Fungal endophyte diversity from tropical forage grass Brachiaria

ABSTRACT

Background

Microbial endophytes can be beneficial to host plants, improving resistance against biotic and abiotic stress. While beneficial fungal endophytes have been well characterised in temperate grasses, knowledge about fungal endophytes of tropical grasses is limited.     

Olive orchard microbiome: characterisation of bacterial communities in soil-plant compartments and their comparison between sustainable and conventional soil management systems

ABSTRACT

Background

Beneficial bacteria-plant interactions play an important role in agriculture, positively affecting plant status and improving product quality. Bacterial endophytes contribute to host plant protection and survival.     

Fungal endophytes associated with Ornithopus compressus growing under semiarid conditions

ABSTRACT

Background

Ornithopus compressus is an important pasture legume of Mediterranean origin that is frequently used for sown pastures under dryland conditions.     

Synthesis of Triazole Nucleoside Derivatives

Abstract

5′-O-Mesyl-2′,3′-O-isopropylidene ribonucleosides (4 and 12) were converted to their 5′-substituted nucleosides in good yields by reacted with NaN₃ or KI. 2′,3′-O-Isopropylidene ribonucleosides (3 and 11) were prepared in good yields from ribonucleosides 1 and 2 with a reaction mixture of acetone and triethyl orthoformate instead of using acetone diethyl acetal. Compound 1 or 2 was treated with 2-acetoxyisobutyryl halide (Cl or Br) to give 1-[2-O-acetyl-3-halo-3-deoxy-5-O-(2,5,5-trimethyl-1,3-dioxolan-4-on-2-yl)-β-D-xylofuranosyl]-1,2,4-triazole-3-carboxamide (19, 22, and 23) in high yields. Instead of using 2-acetoxyisobutyryl bromide, the mixture of 2-acetoxyisobutyryl chloride and NaBr was employed in the synthesis of 22 and 23. Treatment of 19 with an activated Zn/Cu couple and deprotection gave 2′,3′-anhydro nucleoside (21), and treatment of 22 and 23 with an activated Zn/Cu couple and a little of HOAc and deprotection gave corresponding 2′,3′-unsaturated triazole nucleosides (24 and 25), respectively. The biological activity of the compounds (7 ～ 10, 15 ～ 18, and 24) was examined in human liver cancer cells (A-549), lung cancer cells (BEL-7402), and Flu-A cells.

Synthesis of Triazole Nucleoside Derivatives

All authors

Zicheng Li, Shuhua Chen, Ning Jiang & Gang Cui

https://doi.org/10.1081/NCN-120022032

Published online:

07 February 2007

Compound 1.     

5.

Endophytic diversity of hanging velamen roots in the epiphytic orchid Acampe praemorsa     

Azhanthanilkunnathil S. Deepthi 《Plant Ecology & Diversity》2018,11(5-6):649-661

ABSTRACT

Background

The ecological functions of the aerial hanging roots (velamen roots) in orchids are not yet fully understood.     

6.

The Synthesis of [(β‐d‐Ribofuranosyloxy)‐methyl]nucleosides     

《Nucleosides, nucleotides & nucleic acids》2013,32(4):655-669

     

7.

Ichnology Picture     

Ronald K. Pickerill 《Ichnos》2013,20(2)

Ichnology Picture

All authors

Ronald K. Pickerill

https://doi.org/10.1080/10420940600739823

Published online:

26 January 2007

(See Color Plate V)     

8.

Synthesis of 3′-Amino-3′-Deoxyguanosine and 3′-Amino-3′-Deoxyxyloguanosine Monophosphate Hepdirect Prodrugs from Guanosine     

Brett C. Bookser  Nicholas B. Raffaele  K. Raja Reddy  Kevin Fan  Wenjian Huang  Mark D. Erion 《Nucleosides, nucleotides & nucleic acids》2013,32(10):969-986

     

9.

MOLECULAR MODELLING OF 2′-OH MEDIATED HYDROGEN BONDING IN RIBONUCLEOS(T)IDES BY NMR CONSTRAINED AM1 AND MMX CALCULATIONS     

《Nucleosides, nucleotides & nucleic acids》2013,32(4-7):1211-1217

The intra- and intermolecular hydrogen bonding (ΔGº_298K ≈ 2, kcal mol^?1) of 2′-OH in nucleos(t)ides has been reported by the temperature- and concentration-dependent NMR study in conjunction with dihedral dependence of the NMR derived both endo (³ J _H,H)- and exocyclic (³ JH,OH) coupling constants, nOe contacts and lineshape analyses of hydroxyl protons for EtpA (1), 3′-dA (2), rA (3), 2′-dA (4) [Fig. 1] in DMSO-d ₆ at 500 MHz.

MOLECULAR MODELLING OF 2′-OH MEDIATED HYDROGEN BONDING IN RIBONUCLEOS(T)IDES BY NMR CONSTRAINED AM1 AND MMX CALCULATIONS

All authors

Parag Acharya, Irina Velikian, Sandipta Acharya & Jyoti Chattopadhyaya

https://doi.org/10.1081/NCN-100002521

Published online:

07 February 2007

Figure 1. The schematic representation of the bias of the dymanic two-state pseudorotational equilibrium between the North-type (N, C2′-exo -C3′-endo) and the South-type (S, C3′-exo-C2′-endo) [3a] Thibaudeau, C. and Chattopadhyaya, J. 1999. Stereoelectronic Effects in Nucleosides and Nucleotides and their Structural Implications Sweden: (ISBN 91-506-1351-0), Department of Bioorganic Chemistry, Uppsala University Press (fax: +4618554495). For review see: and references therein [Google Scholar] pseudorotamers of the sugar moeity for EtpA (1), 3′-dA (2), rA (3), 2′-dA (4) and torsion (Φ) around C2′/3′-O bond viz. Φ₁ = Φ_{H2′?C2′?O?H} and Φ₂ = Φ_{H3′?C3′?O?H} except in 1 where the torsion across C3′-O3′ bond is actually ?^? [C4′-C3′-O3′-P].     

10.

PHENYLALKYL BACKBONE MODIFIED OLIGODEOXYNUCLEOTIDES,THEIR SYNTHESIS AND THE INFLUENCE OF THE ALKYL CHAIN LENGTH     

《Nucleosides, nucleotides & nucleic acids》2013,32(4-7):1275-1278

Phenylalkyl modified phosphoramidites (alkyl chain length n = 1,2,3,5; Fig. 1) were synthesised and incorporated into a DNA hexamer (5′-d(GCCp-GCG); p = place of modification). The obtained diastereomeres were separated by RP-HPLC. After hybridisation with the complementary DNA strand T_m-value and thermodynamic data were measured. The stability of duplexes depends on the linker length and the absolute configuration of the backbone modified oligodeoxynucleotides (Rp, Sp).

PHENYLALKYL BACKBONE MODIFIED OLIGODEOXYNUCLEOTIDES, THEIR SYNTHESIS AND THE INFLUENCE OF THE ALKYL CHAIN LENGTH

All authors

Stefan Amberg & Joachim W. Engels

https://doi.org/10.1081/NCN-100002535

Published online:

07 February 2007

Figure 1. Structure of Rp- and Sp-configurated oligomers; synthesised phosphoramidites.     

11.

Anthropogenic pressures within the breeding range of the Hen Harrier Circus cyaneus in Ireland     

Anthony Caravaggi  Sandra Irwin  John Lusby  Marc Ruddock  Allan Mee  Tony Nagle 《Bird Study》2019,66(4):461-470

ABSTRACT

Capsule

Patterns in the frequency and co-occurrence of anthropogenic pressures associated with suitable breeding habitat for Hen Harriers Circus cyaneus demonstrates the need for specific, focussed management and policy options aimed at mitigating impacts on this threatened population.     

12.

Host species identity in annual Brassicaceae has a limited effect on the assembly of root-endophytic fungal communities     

Kyriaki Glynou  Marco Thines 《Plant Ecology & Diversity》2018,11(5-6):569-580

ABSTRACT

Background

Establishing the contribution of host plant genotype to the assembly of root-associated microbial communities can be challenging, since multiple ecological factors may confound the effects purely due to the host, and plant species often do not occur sympatrically.     

13.

Epichloë endophyte effects on leaf blotch pathogen (Rhynchosporium sp.) of tall fescue (Schedonorus phoenix) vary among grass origin and environmental conditions     

Miia Kauppinen  Marjo Helander  Noora Anttila  Irma Saloniemi  Kari Saikkonen 《Plant Ecology & Diversity》2018,11(5-6):625-635

ABSTRACT

Background

Systemic Epichloë endophytes are common fungal symbionts of many cool-season grasses. They are known for their capability of increasing host plant tolerance against biotic and abiotic stressors, including grass pathogens. However, results on endophyte-mediated disease resistance have been ambiguous, and the underlying mechanisms of disease resistance remain unknown.     

14.

Side‐Chain Conformational Restriction in Template‐Competitive Inhibitors of E. coliDNA Polymerase I Klenow Fragment: Synthesis,Structural Characterization and Inhibition Activity     

《Nucleosides, nucleotides & nucleic acids》2013,32(11):1751-1765

     

15.

5′-O-[N-(Amnoacyl)Sulfamoyl]Nucleosides. Synthesis and Antiviral and Cytostatic Activities     

Julia Castro-pichel  Ma. Teresa García-López  Rosario Herranz  Concepción Pérez 《Nucleosides, nucleotides & nucleic acids》2013,32(7):985-1000

Abstract

5′-O-[N-(Aminoacyl)sulfamoyl]-uridines and -thymidines 4a-12a and 4b-12b have been synthesized and tested against Herpes Simplex virus type 2 (HSV-2) and as cytostatics. Condensation of 2′,3′-O-isopropylidene-5′-O-sulfamoyluridine and 3′-O-acetyl-5′-O-sulfamoylthymidine with the N-hydroxysuccinimide esters of Boc-L-Ser(Bzl), (2R, 3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbuta-noic acid [(2R, 3S-N-Z-AHPBA], (2R, 3S) and (2S, 3R)-N-Boc-AHPBA gave 4a,b-7a,b, which after removal of the protecting groups provided 1Oa,b-12a,b. A study of the selective removal of the O-Bzl protecting group from the L-Ser derivatives 4a,b, without hydrogenation of the pyrimidine ring, has been carried out. Only the fully protected uridine derivatives 4a-7a did exhibit high anti-HSV-2 activity, and none of the synthesized compounds showed significant cytostatic activity against HeLa cells cultures.     

16.

Synthesis of Brunfelsamidine Ribonucleoside and Certain Related Compounds by the Stereospecific Sodium Salt Glycosylation Procedure     

Kandasamy Ramasamy  Roland K. Robins  Ganapathi R. Revankar 《Nucleosides, nucleotides & nucleic acids》2013,32(3):385-392

Abstract

A synthesis of 2,4-dideazaribavirin ( 2 ), brunfelsamidine ribonucleoside ( 8c ) and certain related derivatives are described for the first time using the stereospecific sodium salt glycosylation procedure. Glycosylation of the sodium salt of pyrrole-3-carbonitrile ( 4 ) with 1-chloro-2, 3-O-t-isopropylidene-5-O-t-butyldimethylsilyl-α-D-ribofuranose ( 5 ) gave exclusively the corresponding blocked nucleoside ( 6 ) with β-anomeric configuration, which on deprotection provided 1-β-D-ribofuranosylpyrrole-3-carbonitrile ( 7 ). Functional group tranformation of 7 gave 2 , 8c and related 3-substituted pyrrole ribonucleosides. These compounds are devoid of any significant antiviral/antitumor activity invitro.     

17.

Placement,survival and predator identity of Eurasian Curlew Numenius arquata nests on lowland grass-heath     

Natalia B. Zielonka  Robert W. Hawkes  Helen Jones  Robert J. Burnside  Paul M. Dolman 《Bird Study》2019,66(4):471-483

ABSTRACT

Capsule

Within the UK’s largest lowland Eurasian Curlew Numenius arquata population, curlew preferentially nested on physically disturbed (treated) than undisturbed (control) grassland, and low nest survival rates were primarily attributable to predation by Red Fox Vulpes vulpes.     

18.

Il Pinus Mugo Turra Ed Il Pinus Uncinata Miller in Piemonte. Note Critiche e Distribuzione     

Franco Montacchini  Rosanna Caramiello 《Plant biosystems》2013,147(6):529-535

Abstract

«Pinus mugo» Turra and «Pinus uncinata» Miller in Piedmont. Critical notes and distribution. — The Authors have carried on a research on the distribution of Pinus mugo Turra (sensu Fl. Eur.) and Pinus uncinata Miller in all Piedmont Alpes and, having observed the extreme variability of the characters which are employed in the keys of determination to differentiate these two species, they suggest other and more constant characters. These are:

Il Pinus Mugo Turra Ed Il Pinus Uncinata Miller in Piemonte. Note Critiche e Distribuzione

All authors

Franco Montacchini & Rosanna Caramiello

https://doi.org/10.1080/11263506809426488

Published online:

14 September 2009

Table     

19.

A New Synthesis of 9-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)guanine (araF-G)     

《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1339-1342

Abstract

Interesting and very promising antisense properties of 2′-deoxy-2′-fluoroarabinonucleic acids ((a) Wilds, C.J.; Damha, M.J. 2′-Deoxy-2′-fluoroarabinonucleosides and oligonucleotides (2′F-ANA): synthesis and physicochemical studies. Nucl. Acids Res. 2000, 28, 3625–3635; (b) Viazovkina, E.; Mangos, M.; Elzagheid, M.I.; Damha, M.J. Current Protocols in Nucleic Acid Chemistry 2002, 4.15.1–4.15.21) (2′F-ANA) has encouraged our research group to optimize the synthetic procedures for 2′-deoxy-2′-fluoro-β-D-arabinonucleosides (araF-N). The synthesis of araF-U, araF-T, araF-A and araF-C is straightforward, (Tann, C.H.; Brodfuehrer, P.R.; Brundidge, S.P.; Sapino, C., Jr. Howell H.G. Fluorocarbohydrates in synthesis. An efficient synthesis of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil (β-FIAU) and 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine (β-FMAU). J. Org. Chem. 1985, 50, 3644–3647; Howell, H.G.; Brodfuehrer, P.R.; Brundidge, S.P.; Benigni, D.A.; Sapino, C., Jr. Antiviral nucleosides. A stereospecific, total synthesis of 2′-fluoro-2′-deoxy-β-D-arabinofuranosyl nucleosides. J. Org. Chem. 1988, 53, 85–88; Maruyama, T.; Takamatsu, S.; Kozai, S.; Satoh, Y.; Izana, K. Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine bearing a selectively removable protecting group. Chem. Pharm. Bull. 1999, 47, 966–970) however, the synthesis of the guanine analogue is more complicated and affords poor to moderate yields of araF-G (4) ((a) Elzagheid, M.I.; Viazovkina, E.; Masad, M.J. Synthesis of protected 2′-deoxy-2′-fluoro-β-D-arabinonucleosides. Synthesis of 2′-fluoroarabino nucleoside phosphoramidites and their use in the synthesis of 2′F-ANA. Current Protocols in Nucleic Acid Chemistry 2002, 1.7.1–1.7.19; (b) Tennila, T.; Azhayeva, E.; Vepsalainen, J.; Laatikainen, R.; Azhayev, A.; Mikhailopulo, I. Oligonucleotides containing 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine and -guanine: synthesis, hybridization and antisense properties. Nucleosides, Nucleotides and Nucl. Acids 2000, 19, 1861–1884). Here we describe an efficient synthesis of araF-G (4) that involves coupling of 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D- arabinofuranosyl bromide (1) with 2-chlorohypoxanthine (2) to afford 2-chloro-β-araF-I (3) in 52% yield. Nucleoside (3) was transformed into araF-G (4) by treatment with methanolic ammonia (150°C, 6 h) in 67% yield.     

20.

Improved and Reliable Synthesis of 3′‐Azido‐2′,3′‐dideoxyguanosine Derivatives     

《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):171-181

An improved synthesis of N²‐protected‐3′‐azido‐2′,3′‐dideoxyguanosine 20 and 23 is described. Deoxygenation of 2′‐O‐alkyl (and/or aryl) sulfonyl‐5′‐dimethoxytritylguanosine coupled with [1,2]‐hydride shift rearrangement gave protected 9‐(2‐deoxy‐threo‐pentofuranosyl)guanines ( 10 , 12 and 16 ). This rearrangement was accomplished in high yield with a high degree of stereoselectivity using lithium triisobutylborohydride (l‐Selectride®). Compounds 10 , 12 and 16 were transformed into 3′‐O‐mesylates ( 18 and 21 ), which can be used for 3′‐substitution. The 3′‐azido nucleosides were obtained by treatment of 18 and 21 with lithium azide. This procedure is reproducible with a good overall yield.     

Endophytic diversity of hanging velamen roots in the epiphytic orchid Acampe praemorsa

ABSTRACT

Background

The ecological functions of the aerial hanging roots (velamen roots) in orchids are not yet fully understood.     

Ichnology Picture

Ichnology Picture

All authors

Ronald K. Pickerill

https://doi.org/10.1080/10420940600739823

Published online:

26 January 2007

(See Color Plate V)     

8.

Synthesis of 3′-Amino-3′-Deoxyguanosine and 3′-Amino-3′-Deoxyxyloguanosine Monophosphate Hepdirect Prodrugs from Guanosine     

Brett C. Bookser  Nicholas B. Raffaele  K. Raja Reddy  Kevin Fan  Wenjian Huang  Mark D. Erion 《Nucleosides, nucleotides & nucleic acids》2013,32(10):969-986

     

9.

MOLECULAR MODELLING OF 2′-OH MEDIATED HYDROGEN BONDING IN RIBONUCLEOS(T)IDES BY NMR CONSTRAINED AM1 AND MMX CALCULATIONS     

《Nucleosides, nucleotides & nucleic acids》2013,32(4-7):1211-1217

The intra- and intermolecular hydrogen bonding (ΔGº_298K ≈ 2, kcal mol^?1) of 2′-OH in nucleos(t)ides has been reported by the temperature- and concentration-dependent NMR study in conjunction with dihedral dependence of the NMR derived both endo (³ J _H,H)- and exocyclic (³ JH,OH) coupling constants, nOe contacts and lineshape analyses of hydroxyl protons for EtpA (1), 3′-dA (2), rA (3), 2′-dA (4) [Fig. 1] in DMSO-d ₆ at 500 MHz.

MOLECULAR MODELLING OF 2′-OH MEDIATED HYDROGEN BONDING IN RIBONUCLEOS(T)IDES BY NMR CONSTRAINED AM1 AND MMX CALCULATIONS

All authors

Parag Acharya, Irina Velikian, Sandipta Acharya & Jyoti Chattopadhyaya

https://doi.org/10.1081/NCN-100002521

Published online:

07 February 2007

Figure 1. The schematic representation of the bias of the dymanic two-state pseudorotational equilibrium between the North-type (N, C2′-exo -C3′-endo) and the South-type (S, C3′-exo-C2′-endo) [3a] Thibaudeau, C. and Chattopadhyaya, J. 1999. Stereoelectronic Effects in Nucleosides and Nucleotides and their Structural Implications Sweden: (ISBN 91-506-1351-0), Department of Bioorganic Chemistry, Uppsala University Press (fax: +4618554495). For review see: and references therein [Google Scholar] pseudorotamers of the sugar moeity for EtpA (1), 3′-dA (2), rA (3), 2′-dA (4) and torsion (Φ) around C2′/3′-O bond viz. Φ₁ = Φ_{H2′?C2′?O?H} and Φ₂ = Φ_{H3′?C3′?O?H} except in 1 where the torsion across C3′-O3′ bond is actually ?^? [C4′-C3′-O3′-P].     

10.

PHENYLALKYL BACKBONE MODIFIED OLIGODEOXYNUCLEOTIDES,THEIR SYNTHESIS AND THE INFLUENCE OF THE ALKYL CHAIN LENGTH     

《Nucleosides, nucleotides & nucleic acids》2013,32(4-7):1275-1278

Phenylalkyl modified phosphoramidites (alkyl chain length n = 1,2,3,5; Fig. 1) were synthesised and incorporated into a DNA hexamer (5′-d(GCCp-GCG); p = place of modification). The obtained diastereomeres were separated by RP-HPLC. After hybridisation with the complementary DNA strand T_m-value and thermodynamic data were measured. The stability of duplexes depends on the linker length and the absolute configuration of the backbone modified oligodeoxynucleotides (Rp, Sp).

PHENYLALKYL BACKBONE MODIFIED OLIGODEOXYNUCLEOTIDES, THEIR SYNTHESIS AND THE INFLUENCE OF THE ALKYL CHAIN LENGTH

All authors

Stefan Amberg & Joachim W. Engels

https://doi.org/10.1081/NCN-100002535

Published online:

07 February 2007

Figure 1. Structure of Rp- and Sp-configurated oligomers; synthesised phosphoramidites.     

11.

Anthropogenic pressures within the breeding range of the Hen Harrier Circus cyaneus in Ireland     

Anthony Caravaggi  Sandra Irwin  John Lusby  Marc Ruddock  Allan Mee  Tony Nagle 《Bird Study》2019,66(4):461-470

ABSTRACT

Capsule

Patterns in the frequency and co-occurrence of anthropogenic pressures associated with suitable breeding habitat for Hen Harriers Circus cyaneus demonstrates the need for specific, focussed management and policy options aimed at mitigating impacts on this threatened population.     

12.

Host species identity in annual Brassicaceae has a limited effect on the assembly of root-endophytic fungal communities     

Kyriaki Glynou  Marco Thines 《Plant Ecology & Diversity》2018,11(5-6):569-580

ABSTRACT

Background

Establishing the contribution of host plant genotype to the assembly of root-associated microbial communities can be challenging, since multiple ecological factors may confound the effects purely due to the host, and plant species often do not occur sympatrically.     

13.

Epichloë endophyte effects on leaf blotch pathogen (Rhynchosporium sp.) of tall fescue (Schedonorus phoenix) vary among grass origin and environmental conditions     

Miia Kauppinen  Marjo Helander  Noora Anttila  Irma Saloniemi  Kari Saikkonen 《Plant Ecology & Diversity》2018,11(5-6):625-635

ABSTRACT

Background

Systemic Epichloë endophytes are common fungal symbionts of many cool-season grasses. They are known for their capability of increasing host plant tolerance against biotic and abiotic stressors, including grass pathogens. However, results on endophyte-mediated disease resistance have been ambiguous, and the underlying mechanisms of disease resistance remain unknown.     

14.

Side‐Chain Conformational Restriction in Template‐Competitive Inhibitors of E. coliDNA Polymerase I Klenow Fragment: Synthesis,Structural Characterization and Inhibition Activity     

《Nucleosides, nucleotides & nucleic acids》2013,32(11):1751-1765

     

15.

5′-O-[N-(Amnoacyl)Sulfamoyl]Nucleosides. Synthesis and Antiviral and Cytostatic Activities     

Julia Castro-pichel  Ma. Teresa García-López  Rosario Herranz  Concepción Pérez 《Nucleosides, nucleotides & nucleic acids》2013,32(7):985-1000

Abstract

5′-O-[N-(Aminoacyl)sulfamoyl]-uridines and -thymidines 4a-12a and 4b-12b have been synthesized and tested against Herpes Simplex virus type 2 (HSV-2) and as cytostatics. Condensation of 2′,3′-O-isopropylidene-5′-O-sulfamoyluridine and 3′-O-acetyl-5′-O-sulfamoylthymidine with the N-hydroxysuccinimide esters of Boc-L-Ser(Bzl), (2R, 3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbuta-noic acid [(2R, 3S-N-Z-AHPBA], (2R, 3S) and (2S, 3R)-N-Boc-AHPBA gave 4a,b-7a,b, which after removal of the protecting groups provided 1Oa,b-12a,b. A study of the selective removal of the O-Bzl protecting group from the L-Ser derivatives 4a,b, without hydrogenation of the pyrimidine ring, has been carried out. Only the fully protected uridine derivatives 4a-7a did exhibit high anti-HSV-2 activity, and none of the synthesized compounds showed significant cytostatic activity against HeLa cells cultures.     

16.

Synthesis of Brunfelsamidine Ribonucleoside and Certain Related Compounds by the Stereospecific Sodium Salt Glycosylation Procedure     

Kandasamy Ramasamy  Roland K. Robins  Ganapathi R. Revankar 《Nucleosides, nucleotides & nucleic acids》2013,32(3):385-392

Abstract

A synthesis of 2,4-dideazaribavirin ( 2 ), brunfelsamidine ribonucleoside ( 8c ) and certain related derivatives are described for the first time using the stereospecific sodium salt glycosylation procedure. Glycosylation of the sodium salt of pyrrole-3-carbonitrile ( 4 ) with 1-chloro-2, 3-O-t-isopropylidene-5-O-t-butyldimethylsilyl-α-D-ribofuranose ( 5 ) gave exclusively the corresponding blocked nucleoside ( 6 ) with β-anomeric configuration, which on deprotection provided 1-β-D-ribofuranosylpyrrole-3-carbonitrile ( 7 ). Functional group tranformation of 7 gave 2 , 8c and related 3-substituted pyrrole ribonucleosides. These compounds are devoid of any significant antiviral/antitumor activity invitro.     

17.

Placement,survival and predator identity of Eurasian Curlew Numenius arquata nests on lowland grass-heath     

Natalia B. Zielonka  Robert W. Hawkes  Helen Jones  Robert J. Burnside  Paul M. Dolman 《Bird Study》2019,66(4):471-483

ABSTRACT

Capsule

Within the UK’s largest lowland Eurasian Curlew Numenius arquata population, curlew preferentially nested on physically disturbed (treated) than undisturbed (control) grassland, and low nest survival rates were primarily attributable to predation by Red Fox Vulpes vulpes.     

18.

Il Pinus Mugo Turra Ed Il Pinus Uncinata Miller in Piemonte. Note Critiche e Distribuzione     

Franco Montacchini  Rosanna Caramiello 《Plant biosystems》2013,147(6):529-535

Abstract

«Pinus mugo» Turra and «Pinus uncinata» Miller in Piedmont. Critical notes and distribution. — The Authors have carried on a research on the distribution of Pinus mugo Turra (sensu Fl. Eur.) and Pinus uncinata Miller in all Piedmont Alpes and, having observed the extreme variability of the characters which are employed in the keys of determination to differentiate these two species, they suggest other and more constant characters. These are:

Il Pinus Mugo Turra Ed Il Pinus Uncinata Miller in Piemonte. Note Critiche e Distribuzione

All authors

Franco Montacchini & Rosanna Caramiello

https://doi.org/10.1080/11263506809426488

Published online:

14 September 2009

Table     

19.

A New Synthesis of 9-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)guanine (araF-G)     

《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1339-1342

Abstract

Interesting and very promising antisense properties of 2′-deoxy-2′-fluoroarabinonucleic acids ((a) Wilds, C.J.; Damha, M.J. 2′-Deoxy-2′-fluoroarabinonucleosides and oligonucleotides (2′F-ANA): synthesis and physicochemical studies. Nucl. Acids Res. 2000, 28, 3625–3635; (b) Viazovkina, E.; Mangos, M.; Elzagheid, M.I.; Damha, M.J. Current Protocols in Nucleic Acid Chemistry 2002, 4.15.1–4.15.21) (2′F-ANA) has encouraged our research group to optimize the synthetic procedures for 2′-deoxy-2′-fluoro-β-D-arabinonucleosides (araF-N). The synthesis of araF-U, araF-T, araF-A and araF-C is straightforward, (Tann, C.H.; Brodfuehrer, P.R.; Brundidge, S.P.; Sapino, C., Jr. Howell H.G. Fluorocarbohydrates in synthesis. An efficient synthesis of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil (β-FIAU) and 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine (β-FMAU). J. Org. Chem. 1985, 50, 3644–3647; Howell, H.G.; Brodfuehrer, P.R.; Brundidge, S.P.; Benigni, D.A.; Sapino, C., Jr. Antiviral nucleosides. A stereospecific, total synthesis of 2′-fluoro-2′-deoxy-β-D-arabinofuranosyl nucleosides. J. Org. Chem. 1988, 53, 85–88; Maruyama, T.; Takamatsu, S.; Kozai, S.; Satoh, Y.; Izana, K. Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine bearing a selectively removable protecting group. Chem. Pharm. Bull. 1999, 47, 966–970) however, the synthesis of the guanine analogue is more complicated and affords poor to moderate yields of araF-G (4) ((a) Elzagheid, M.I.; Viazovkina, E.; Masad, M.J. Synthesis of protected 2′-deoxy-2′-fluoro-β-D-arabinonucleosides. Synthesis of 2′-fluoroarabino nucleoside phosphoramidites and their use in the synthesis of 2′F-ANA. Current Protocols in Nucleic Acid Chemistry 2002, 1.7.1–1.7.19; (b) Tennila, T.; Azhayeva, E.; Vepsalainen, J.; Laatikainen, R.; Azhayev, A.; Mikhailopulo, I. Oligonucleotides containing 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine and -guanine: synthesis, hybridization and antisense properties. Nucleosides, Nucleotides and Nucl. Acids 2000, 19, 1861–1884). Here we describe an efficient synthesis of araF-G (4) that involves coupling of 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D- arabinofuranosyl bromide (1) with 2-chlorohypoxanthine (2) to afford 2-chloro-β-araF-I (3) in 52% yield. Nucleoside (3) was transformed into araF-G (4) by treatment with methanolic ammonia (150°C, 6 h) in 67% yield.     

20.

Improved and Reliable Synthesis of 3′‐Azido‐2′,3′‐dideoxyguanosine Derivatives     

《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):171-181

An improved synthesis of N²‐protected‐3′‐azido‐2′,3′‐dideoxyguanosine 20 and 23 is described. Deoxygenation of 2′‐O‐alkyl (and/or aryl) sulfonyl‐5′‐dimethoxytritylguanosine coupled with [1,2]‐hydride shift rearrangement gave protected 9‐(2‐deoxy‐threo‐pentofuranosyl)guanines ( 10 , 12 and 16 ). This rearrangement was accomplished in high yield with a high degree of stereoselectivity using lithium triisobutylborohydride (l‐Selectride®). Compounds 10 , 12 and 16 were transformed into 3′‐O‐mesylates ( 18 and 21 ), which can be used for 3′‐substitution. The 3′‐azido nucleosides were obtained by treatment of 18 and 21 with lithium azide. This procedure is reproducible with a good overall yield.     

MOLECULAR MODELLING OF 2′-OH MEDIATED HYDROGEN BONDING IN RIBONUCLEOS(T)IDES BY NMR CONSTRAINED AM1 AND MMX CALCULATIONS

The intra- and intermolecular hydrogen bonding (ΔGº_298K ≈ 2, kcal mol^?1) of 2′-OH in nucleos(t)ides has been reported by the temperature- and concentration-dependent NMR study in conjunction with dihedral dependence of the NMR derived both endo (³ J _H,H)- and exocyclic (³ JH,OH) coupling constants, nOe contacts and lineshape analyses of hydroxyl protons for EtpA (1), 3′-dA (2), rA (3), 2′-dA (4) [Fig. 1] in DMSO-d ₆ at 500 MHz.

MOLECULAR MODELLING OF 2′-OH MEDIATED HYDROGEN BONDING IN RIBONUCLEOS(T)IDES BY NMR CONSTRAINED AM1 AND MMX CALCULATIONS

All authors

Parag Acharya, Irina Velikian, Sandipta Acharya & Jyoti Chattopadhyaya

https://doi.org/10.1081/NCN-100002521

Published online:

07 February 2007

Figure 1. The schematic representation of the bias of the dymanic two-state pseudorotational equilibrium between the North-type (N, C2′-exo -C3′-endo) and the South-type (S, C3′-exo-C2′-endo) [3a] Thibaudeau, C. and Chattopadhyaya, J. 1999. Stereoelectronic Effects in Nucleosides and Nucleotides and their Structural Implications Sweden: (ISBN 91-506-1351-0), Department of Bioorganic Chemistry, Uppsala University Press (fax: +4618554495). For review see: and references therein [Google Scholar] pseudorotamers of the sugar moeity for EtpA (1), 3′-dA (2), rA (3), 2′-dA (4) and torsion (Φ) around C2′/3′-O bond viz. Φ₁ = Φ_{H2′?C2′?O?H} and Φ₂ = Φ_{H3′?C3′?O?H} except in 1 where the torsion across C3′-O3′ bond is actually ?^? [C4′-C3′-O3′-P].     

10.

PHENYLALKYL BACKBONE MODIFIED OLIGODEOXYNUCLEOTIDES,THEIR SYNTHESIS AND THE INFLUENCE OF THE ALKYL CHAIN LENGTH     

《Nucleosides, nucleotides & nucleic acids》2013,32(4-7):1275-1278

Phenylalkyl modified phosphoramidites (alkyl chain length n = 1,2,3,5; Fig. 1) were synthesised and incorporated into a DNA hexamer (5′-d(GCCp-GCG); p = place of modification). The obtained diastereomeres were separated by RP-HPLC. After hybridisation with the complementary DNA strand T_m-value and thermodynamic data were measured. The stability of duplexes depends on the linker length and the absolute configuration of the backbone modified oligodeoxynucleotides (Rp, Sp).

PHENYLALKYL BACKBONE MODIFIED OLIGODEOXYNUCLEOTIDES, THEIR SYNTHESIS AND THE INFLUENCE OF THE ALKYL CHAIN LENGTH

All authors

Stefan Amberg & Joachim W. Engels

https://doi.org/10.1081/NCN-100002535

Published online:

07 February 2007

Figure 1. Structure of Rp- and Sp-configurated oligomers; synthesised phosphoramidites.     

11.

Anthropogenic pressures within the breeding range of the Hen Harrier Circus cyaneus in Ireland     

Anthony Caravaggi  Sandra Irwin  John Lusby  Marc Ruddock  Allan Mee  Tony Nagle 《Bird Study》2019,66(4):461-470

ABSTRACT

Capsule

Patterns in the frequency and co-occurrence of anthropogenic pressures associated with suitable breeding habitat for Hen Harriers Circus cyaneus demonstrates the need for specific, focussed management and policy options aimed at mitigating impacts on this threatened population.     

12.

Host species identity in annual Brassicaceae has a limited effect on the assembly of root-endophytic fungal communities     

Kyriaki Glynou  Marco Thines 《Plant Ecology & Diversity》2018,11(5-6):569-580

ABSTRACT

Background

Establishing the contribution of host plant genotype to the assembly of root-associated microbial communities can be challenging, since multiple ecological factors may confound the effects purely due to the host, and plant species often do not occur sympatrically.     

13.

Epichloë endophyte effects on leaf blotch pathogen (Rhynchosporium sp.) of tall fescue (Schedonorus phoenix) vary among grass origin and environmental conditions     

Miia Kauppinen  Marjo Helander  Noora Anttila  Irma Saloniemi  Kari Saikkonen 《Plant Ecology & Diversity》2018,11(5-6):625-635

ABSTRACT

Background

Systemic Epichloë endophytes are common fungal symbionts of many cool-season grasses. They are known for their capability of increasing host plant tolerance against biotic and abiotic stressors, including grass pathogens. However, results on endophyte-mediated disease resistance have been ambiguous, and the underlying mechanisms of disease resistance remain unknown.     

14.

Side‐Chain Conformational Restriction in Template‐Competitive Inhibitors of E. coliDNA Polymerase I Klenow Fragment: Synthesis,Structural Characterization and Inhibition Activity     

《Nucleosides, nucleotides & nucleic acids》2013,32(11):1751-1765

     

15.

5′-O-[N-(Amnoacyl)Sulfamoyl]Nucleosides. Synthesis and Antiviral and Cytostatic Activities     

Julia Castro-pichel  Ma. Teresa García-López  Rosario Herranz  Concepción Pérez 《Nucleosides, nucleotides & nucleic acids》2013,32(7):985-1000

Abstract

5′-O-[N-(Aminoacyl)sulfamoyl]-uridines and -thymidines 4a-12a and 4b-12b have been synthesized and tested against Herpes Simplex virus type 2 (HSV-2) and as cytostatics. Condensation of 2′,3′-O-isopropylidene-5′-O-sulfamoyluridine and 3′-O-acetyl-5′-O-sulfamoylthymidine with the N-hydroxysuccinimide esters of Boc-L-Ser(Bzl), (2R, 3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbuta-noic acid [(2R, 3S-N-Z-AHPBA], (2R, 3S) and (2S, 3R)-N-Boc-AHPBA gave 4a,b-7a,b, which after removal of the protecting groups provided 1Oa,b-12a,b. A study of the selective removal of the O-Bzl protecting group from the L-Ser derivatives 4a,b, without hydrogenation of the pyrimidine ring, has been carried out. Only the fully protected uridine derivatives 4a-7a did exhibit high anti-HSV-2 activity, and none of the synthesized compounds showed significant cytostatic activity against HeLa cells cultures.     

16.

Synthesis of Brunfelsamidine Ribonucleoside and Certain Related Compounds by the Stereospecific Sodium Salt Glycosylation Procedure     

Kandasamy Ramasamy  Roland K. Robins  Ganapathi R. Revankar 《Nucleosides, nucleotides & nucleic acids》2013,32(3):385-392

Abstract

A synthesis of 2,4-dideazaribavirin ( 2 ), brunfelsamidine ribonucleoside ( 8c ) and certain related derivatives are described for the first time using the stereospecific sodium salt glycosylation procedure. Glycosylation of the sodium salt of pyrrole-3-carbonitrile ( 4 ) with 1-chloro-2, 3-O-t-isopropylidene-5-O-t-butyldimethylsilyl-α-D-ribofuranose ( 5 ) gave exclusively the corresponding blocked nucleoside ( 6 ) with β-anomeric configuration, which on deprotection provided 1-β-D-ribofuranosylpyrrole-3-carbonitrile ( 7 ). Functional group tranformation of 7 gave 2 , 8c and related 3-substituted pyrrole ribonucleosides. These compounds are devoid of any significant antiviral/antitumor activity invitro.     

17.

Placement,survival and predator identity of Eurasian Curlew Numenius arquata nests on lowland grass-heath     

Natalia B. Zielonka  Robert W. Hawkes  Helen Jones  Robert J. Burnside  Paul M. Dolman 《Bird Study》2019,66(4):471-483

ABSTRACT

Capsule

Within the UK’s largest lowland Eurasian Curlew Numenius arquata population, curlew preferentially nested on physically disturbed (treated) than undisturbed (control) grassland, and low nest survival rates were primarily attributable to predation by Red Fox Vulpes vulpes.     

18.

Il Pinus Mugo Turra Ed Il Pinus Uncinata Miller in Piemonte. Note Critiche e Distribuzione     

Franco Montacchini  Rosanna Caramiello 《Plant biosystems》2013,147(6):529-535

Abstract

«Pinus mugo» Turra and «Pinus uncinata» Miller in Piedmont. Critical notes and distribution. — The Authors have carried on a research on the distribution of Pinus mugo Turra (sensu Fl. Eur.) and Pinus uncinata Miller in all Piedmont Alpes and, having observed the extreme variability of the characters which are employed in the keys of determination to differentiate these two species, they suggest other and more constant characters. These are:

Il Pinus Mugo Turra Ed Il Pinus Uncinata Miller in Piemonte. Note Critiche e Distribuzione

All authors

Franco Montacchini & Rosanna Caramiello

https://doi.org/10.1080/11263506809426488

Published online:

14 September 2009

Table     

19.

A New Synthesis of 9-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)guanine (araF-G)     

《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1339-1342

Abstract

Interesting and very promising antisense properties of 2′-deoxy-2′-fluoroarabinonucleic acids ((a) Wilds, C.J.; Damha, M.J. 2′-Deoxy-2′-fluoroarabinonucleosides and oligonucleotides (2′F-ANA): synthesis and physicochemical studies. Nucl. Acids Res. 2000, 28, 3625–3635; (b) Viazovkina, E.; Mangos, M.; Elzagheid, M.I.; Damha, M.J. Current Protocols in Nucleic Acid Chemistry 2002, 4.15.1–4.15.21) (2′F-ANA) has encouraged our research group to optimize the synthetic procedures for 2′-deoxy-2′-fluoro-β-D-arabinonucleosides (araF-N). The synthesis of araF-U, araF-T, araF-A and araF-C is straightforward, (Tann, C.H.; Brodfuehrer, P.R.; Brundidge, S.P.; Sapino, C., Jr. Howell H.G. Fluorocarbohydrates in synthesis. An efficient synthesis of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil (β-FIAU) and 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine (β-FMAU). J. Org. Chem. 1985, 50, 3644–3647; Howell, H.G.; Brodfuehrer, P.R.; Brundidge, S.P.; Benigni, D.A.; Sapino, C., Jr. Antiviral nucleosides. A stereospecific, total synthesis of 2′-fluoro-2′-deoxy-β-D-arabinofuranosyl nucleosides. J. Org. Chem. 1988, 53, 85–88; Maruyama, T.; Takamatsu, S.; Kozai, S.; Satoh, Y.; Izana, K. Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine bearing a selectively removable protecting group. Chem. Pharm. Bull. 1999, 47, 966–970) however, the synthesis of the guanine analogue is more complicated and affords poor to moderate yields of araF-G (4) ((a) Elzagheid, M.I.; Viazovkina, E.; Masad, M.J. Synthesis of protected 2′-deoxy-2′-fluoro-β-D-arabinonucleosides. Synthesis of 2′-fluoroarabino nucleoside phosphoramidites and their use in the synthesis of 2′F-ANA. Current Protocols in Nucleic Acid Chemistry 2002, 1.7.1–1.7.19; (b) Tennila, T.; Azhayeva, E.; Vepsalainen, J.; Laatikainen, R.; Azhayev, A.; Mikhailopulo, I. Oligonucleotides containing 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine and -guanine: synthesis, hybridization and antisense properties. Nucleosides, Nucleotides and Nucl. Acids 2000, 19, 1861–1884). Here we describe an efficient synthesis of araF-G (4) that involves coupling of 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D- arabinofuranosyl bromide (1) with 2-chlorohypoxanthine (2) to afford 2-chloro-β-araF-I (3) in 52% yield. Nucleoside (3) was transformed into araF-G (4) by treatment with methanolic ammonia (150°C, 6 h) in 67% yield.     

20.

Improved and Reliable Synthesis of 3′‐Azido‐2′,3′‐dideoxyguanosine Derivatives     

《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):171-181

An improved synthesis of N²‐protected‐3′‐azido‐2′,3′‐dideoxyguanosine 20 and 23 is described. Deoxygenation of 2′‐O‐alkyl (and/or aryl) sulfonyl‐5′‐dimethoxytritylguanosine coupled with [1,2]‐hydride shift rearrangement gave protected 9‐(2‐deoxy‐threo‐pentofuranosyl)guanines ( 10 , 12 and 16 ). This rearrangement was accomplished in high yield with a high degree of stereoselectivity using lithium triisobutylborohydride (l‐Selectride®). Compounds 10 , 12 and 16 were transformed into 3′‐O‐mesylates ( 18 and 21 ), which can be used for 3′‐substitution. The 3′‐azido nucleosides were obtained by treatment of 18 and 21 with lithium azide. This procedure is reproducible with a good overall yield.     

PHENYLALKYL BACKBONE MODIFIED OLIGODEOXYNUCLEOTIDES,THEIR SYNTHESIS AND THE INFLUENCE OF THE ALKYL CHAIN LENGTH

Phenylalkyl modified phosphoramidites (alkyl chain length n = 1,2,3,5; Fig. 1) were synthesised and incorporated into a DNA hexamer (5′-d(GCCp-GCG); p = place of modification). The obtained diastereomeres were separated by RP-HPLC. After hybridisation with the complementary DNA strand T_m-value and thermodynamic data were measured. The stability of duplexes depends on the linker length and the absolute configuration of the backbone modified oligodeoxynucleotides (Rp, Sp).

PHENYLALKYL BACKBONE MODIFIED OLIGODEOXYNUCLEOTIDES, THEIR SYNTHESIS AND THE INFLUENCE OF THE ALKYL CHAIN LENGTH

All authors

Stefan Amberg & Joachim W. Engels

https://doi.org/10.1081/NCN-100002535

Published online:

07 February 2007

Figure 1. Structure of Rp- and Sp-configurated oligomers; synthesised phosphoramidites.     

11.

Anthropogenic pressures within the breeding range of the Hen Harrier Circus cyaneus in Ireland     

Anthony Caravaggi  Sandra Irwin  John Lusby  Marc Ruddock  Allan Mee  Tony Nagle 《Bird Study》2019,66(4):461-470

ABSTRACT

Capsule

Patterns in the frequency and co-occurrence of anthropogenic pressures associated with suitable breeding habitat for Hen Harriers Circus cyaneus demonstrates the need for specific, focussed management and policy options aimed at mitigating impacts on this threatened population.     

12.

Host species identity in annual Brassicaceae has a limited effect on the assembly of root-endophytic fungal communities     

Kyriaki Glynou  Marco Thines 《Plant Ecology & Diversity》2018,11(5-6):569-580

ABSTRACT

Background

Establishing the contribution of host plant genotype to the assembly of root-associated microbial communities can be challenging, since multiple ecological factors may confound the effects purely due to the host, and plant species often do not occur sympatrically.     

13.

Epichloë endophyte effects on leaf blotch pathogen (Rhynchosporium sp.) of tall fescue (Schedonorus phoenix) vary among grass origin and environmental conditions     

Miia Kauppinen  Marjo Helander  Noora Anttila  Irma Saloniemi  Kari Saikkonen 《Plant Ecology & Diversity》2018,11(5-6):625-635

ABSTRACT

Background

Systemic Epichloë endophytes are common fungal symbionts of many cool-season grasses. They are known for their capability of increasing host plant tolerance against biotic and abiotic stressors, including grass pathogens. However, results on endophyte-mediated disease resistance have been ambiguous, and the underlying mechanisms of disease resistance remain unknown.     

14.

Side‐Chain Conformational Restriction in Template‐Competitive Inhibitors of E. coliDNA Polymerase I Klenow Fragment: Synthesis,Structural Characterization and Inhibition Activity     

《Nucleosides, nucleotides & nucleic acids》2013,32(11):1751-1765

     

15.

5′-O-[N-(Amnoacyl)Sulfamoyl]Nucleosides. Synthesis and Antiviral and Cytostatic Activities     

Julia Castro-pichel  Ma. Teresa García-López  Rosario Herranz  Concepción Pérez 《Nucleosides, nucleotides & nucleic acids》2013,32(7):985-1000

Abstract

5′-O-[N-(Aminoacyl)sulfamoyl]-uridines and -thymidines 4a-12a and 4b-12b have been synthesized and tested against Herpes Simplex virus type 2 (HSV-2) and as cytostatics. Condensation of 2′,3′-O-isopropylidene-5′-O-sulfamoyluridine and 3′-O-acetyl-5′-O-sulfamoylthymidine with the N-hydroxysuccinimide esters of Boc-L-Ser(Bzl), (2R, 3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbuta-noic acid [(2R, 3S-N-Z-AHPBA], (2R, 3S) and (2S, 3R)-N-Boc-AHPBA gave 4a,b-7a,b, which after removal of the protecting groups provided 1Oa,b-12a,b. A study of the selective removal of the O-Bzl protecting group from the L-Ser derivatives 4a,b, without hydrogenation of the pyrimidine ring, has been carried out. Only the fully protected uridine derivatives 4a-7a did exhibit high anti-HSV-2 activity, and none of the synthesized compounds showed significant cytostatic activity against HeLa cells cultures.     

16.

Synthesis of Brunfelsamidine Ribonucleoside and Certain Related Compounds by the Stereospecific Sodium Salt Glycosylation Procedure     

Kandasamy Ramasamy  Roland K. Robins  Ganapathi R. Revankar 《Nucleosides, nucleotides & nucleic acids》2013,32(3):385-392

Abstract

A synthesis of 2,4-dideazaribavirin ( 2 ), brunfelsamidine ribonucleoside ( 8c ) and certain related derivatives are described for the first time using the stereospecific sodium salt glycosylation procedure. Glycosylation of the sodium salt of pyrrole-3-carbonitrile ( 4 ) with 1-chloro-2, 3-O-t-isopropylidene-5-O-t-butyldimethylsilyl-α-D-ribofuranose ( 5 ) gave exclusively the corresponding blocked nucleoside ( 6 ) with β-anomeric configuration, which on deprotection provided 1-β-D-ribofuranosylpyrrole-3-carbonitrile ( 7 ). Functional group tranformation of 7 gave 2 , 8c and related 3-substituted pyrrole ribonucleosides. These compounds are devoid of any significant antiviral/antitumor activity invitro.     

17.

Placement,survival and predator identity of Eurasian Curlew Numenius arquata nests on lowland grass-heath     

Natalia B. Zielonka  Robert W. Hawkes  Helen Jones  Robert J. Burnside  Paul M. Dolman 《Bird Study》2019,66(4):471-483

ABSTRACT

Capsule

Within the UK’s largest lowland Eurasian Curlew Numenius arquata population, curlew preferentially nested on physically disturbed (treated) than undisturbed (control) grassland, and low nest survival rates were primarily attributable to predation by Red Fox Vulpes vulpes.     

18.

Il Pinus Mugo Turra Ed Il Pinus Uncinata Miller in Piemonte. Note Critiche e Distribuzione     

Franco Montacchini  Rosanna Caramiello 《Plant biosystems》2013,147(6):529-535

Abstract

«Pinus mugo» Turra and «Pinus uncinata» Miller in Piedmont. Critical notes and distribution. — The Authors have carried on a research on the distribution of Pinus mugo Turra (sensu Fl. Eur.) and Pinus uncinata Miller in all Piedmont Alpes and, having observed the extreme variability of the characters which are employed in the keys of determination to differentiate these two species, they suggest other and more constant characters. These are:

Il Pinus Mugo Turra Ed Il Pinus Uncinata Miller in Piemonte. Note Critiche e Distribuzione

All authors

Franco Montacchini & Rosanna Caramiello

https://doi.org/10.1080/11263506809426488

Published online:

14 September 2009

Table     

19.

A New Synthesis of 9-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)guanine (araF-G)     

《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1339-1342

Abstract

Interesting and very promising antisense properties of 2′-deoxy-2′-fluoroarabinonucleic acids ((a) Wilds, C.J.; Damha, M.J. 2′-Deoxy-2′-fluoroarabinonucleosides and oligonucleotides (2′F-ANA): synthesis and physicochemical studies. Nucl. Acids Res. 2000, 28, 3625–3635; (b) Viazovkina, E.; Mangos, M.; Elzagheid, M.I.; Damha, M.J. Current Protocols in Nucleic Acid Chemistry 2002, 4.15.1–4.15.21) (2′F-ANA) has encouraged our research group to optimize the synthetic procedures for 2′-deoxy-2′-fluoro-β-D-arabinonucleosides (araF-N). The synthesis of araF-U, araF-T, araF-A and araF-C is straightforward, (Tann, C.H.; Brodfuehrer, P.R.; Brundidge, S.P.; Sapino, C., Jr. Howell H.G. Fluorocarbohydrates in synthesis. An efficient synthesis of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil (β-FIAU) and 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine (β-FMAU). J. Org. Chem. 1985, 50, 3644–3647; Howell, H.G.; Brodfuehrer, P.R.; Brundidge, S.P.; Benigni, D.A.; Sapino, C., Jr. Antiviral nucleosides. A stereospecific, total synthesis of 2′-fluoro-2′-deoxy-β-D-arabinofuranosyl nucleosides. J. Org. Chem. 1988, 53, 85–88; Maruyama, T.; Takamatsu, S.; Kozai, S.; Satoh, Y.; Izana, K. Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine bearing a selectively removable protecting group. Chem. Pharm. Bull. 1999, 47, 966–970) however, the synthesis of the guanine analogue is more complicated and affords poor to moderate yields of araF-G (4) ((a) Elzagheid, M.I.; Viazovkina, E.; Masad, M.J. Synthesis of protected 2′-deoxy-2′-fluoro-β-D-arabinonucleosides. Synthesis of 2′-fluoroarabino nucleoside phosphoramidites and their use in the synthesis of 2′F-ANA. Current Protocols in Nucleic Acid Chemistry 2002, 1.7.1–1.7.19; (b) Tennila, T.; Azhayeva, E.; Vepsalainen, J.; Laatikainen, R.; Azhayev, A.; Mikhailopulo, I. Oligonucleotides containing 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine and -guanine: synthesis, hybridization and antisense properties. Nucleosides, Nucleotides and Nucl. Acids 2000, 19, 1861–1884). Here we describe an efficient synthesis of araF-G (4) that involves coupling of 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D- arabinofuranosyl bromide (1) with 2-chlorohypoxanthine (2) to afford 2-chloro-β-araF-I (3) in 52% yield. Nucleoside (3) was transformed into araF-G (4) by treatment with methanolic ammonia (150°C, 6 h) in 67% yield.     

20.

Improved and Reliable Synthesis of 3′‐Azido‐2′,3′‐dideoxyguanosine Derivatives     

《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):171-181

An improved synthesis of N²‐protected‐3′‐azido‐2′,3′‐dideoxyguanosine 20 and 23 is described. Deoxygenation of 2′‐O‐alkyl (and/or aryl) sulfonyl‐5′‐dimethoxytritylguanosine coupled with [1,2]‐hydride shift rearrangement gave protected 9‐(2‐deoxy‐threo‐pentofuranosyl)guanines ( 10 , 12 and 16 ). This rearrangement was accomplished in high yield with a high degree of stereoselectivity using lithium triisobutylborohydride (l‐Selectride®). Compounds 10 , 12 and 16 were transformed into 3′‐O‐mesylates ( 18 and 21 ), which can be used for 3′‐substitution. The 3′‐azido nucleosides were obtained by treatment of 18 and 21 with lithium azide. This procedure is reproducible with a good overall yield.     

Anthropogenic pressures within the breeding range of the Hen Harrier Circus cyaneus in Ireland

ABSTRACT

Capsule

Patterns in the frequency and co-occurrence of anthropogenic pressures associated with suitable breeding habitat for Hen Harriers Circus cyaneus demonstrates the need for specific, focussed management and policy options aimed at mitigating impacts on this threatened population.     

Host species identity in annual Brassicaceae has a limited effect on the assembly of root-endophytic fungal communities

ABSTRACT

Background

Establishing the contribution of host plant genotype to the assembly of root-associated microbial communities can be challenging, since multiple ecological factors may confound the effects purely due to the host, and plant species often do not occur sympatrically.     

Epichloë endophyte effects on leaf blotch pathogen (Rhynchosporium sp.) of tall fescue (Schedonorus phoenix) vary among grass origin and environmental conditions

ABSTRACT

Background

Systemic Epichloë endophytes are common fungal symbionts of many cool-season grasses. They are known for their capability of increasing host plant tolerance against biotic and abiotic stressors, including grass pathogens. However, results on endophyte-mediated disease resistance have been ambiguous, and the underlying mechanisms of disease resistance remain unknown.     

5′-O-[N-(Amnoacyl)Sulfamoyl]Nucleosides. Synthesis and Antiviral and Cytostatic Activities

Abstract

5′-O-[N-(Aminoacyl)sulfamoyl]-uridines and -thymidines 4a-12a and 4b-12b have been synthesized and tested against Herpes Simplex virus type 2 (HSV-2) and as cytostatics. Condensation of 2′,3′-O-isopropylidene-5′-O-sulfamoyluridine and 3′-O-acetyl-5′-O-sulfamoylthymidine with the N-hydroxysuccinimide esters of Boc-L-Ser(Bzl), (2R, 3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbuta-noic acid [(2R, 3S-N-Z-AHPBA], (2R, 3S) and (2S, 3R)-N-Boc-AHPBA gave 4a,b-7a,b, which after removal of the protecting groups provided 1Oa,b-12a,b. A study of the selective removal of the O-Bzl protecting group from the L-Ser derivatives 4a,b, without hydrogenation of the pyrimidine ring, has been carried out. Only the fully protected uridine derivatives 4a-7a did exhibit high anti-HSV-2 activity, and none of the synthesized compounds showed significant cytostatic activity against HeLa cells cultures.     

Synthesis of Brunfelsamidine Ribonucleoside and Certain Related Compounds by the Stereospecific Sodium Salt Glycosylation Procedure

Abstract

A synthesis of 2,4-dideazaribavirin ( 2 ), brunfelsamidine ribonucleoside ( 8c ) and certain related derivatives are described for the first time using the stereospecific sodium salt glycosylation procedure. Glycosylation of the sodium salt of pyrrole-3-carbonitrile ( 4 ) with 1-chloro-2, 3-O-t-isopropylidene-5-O-t-butyldimethylsilyl-α-D-ribofuranose ( 5 ) gave exclusively the corresponding blocked nucleoside ( 6 ) with β-anomeric configuration, which on deprotection provided 1-β-D-ribofuranosylpyrrole-3-carbonitrile ( 7 ). Functional group tranformation of 7 gave 2 , 8c and related 3-substituted pyrrole ribonucleosides. These compounds are devoid of any significant antiviral/antitumor activity invitro.     

Placement,survival and predator identity of Eurasian Curlew Numenius arquata nests on lowland grass-heath

ABSTRACT

Capsule

Within the UK’s largest lowland Eurasian Curlew Numenius arquata population, curlew preferentially nested on physically disturbed (treated) than undisturbed (control) grassland, and low nest survival rates were primarily attributable to predation by Red Fox Vulpes vulpes.     

Il Pinus Mugo Turra Ed Il Pinus Uncinata Miller in Piemonte. Note Critiche e Distribuzione

Abstract

«Pinus mugo» Turra and «Pinus uncinata» Miller in Piedmont. Critical notes and distribution. — The Authors have carried on a research on the distribution of Pinus mugo Turra (sensu Fl. Eur.) and Pinus uncinata Miller in all Piedmont Alpes and, having observed the extreme variability of the characters which are employed in the keys of determination to differentiate these two species, they suggest other and more constant characters. These are:

Il Pinus Mugo Turra Ed Il Pinus Uncinata Miller in Piemonte. Note Critiche e Distribuzione

All authors

Franco Montacchini & Rosanna Caramiello

https://doi.org/10.1080/11263506809426488

Published online:

14 September 2009

Table     

A New Synthesis of 9-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)guanine (araF-G)

Abstract

Interesting and very promising antisense properties of 2′-deoxy-2′-fluoroarabinonucleic acids ((a) Wilds, C.J.; Damha, M.J. 2′-Deoxy-2′-fluoroarabinonucleosides and oligonucleotides (2′F-ANA): synthesis and physicochemical studies. Nucl. Acids Res. 2000, 28, 3625–3635; (b) Viazovkina, E.; Mangos, M.; Elzagheid, M.I.; Damha, M.J. Current Protocols in Nucleic Acid Chemistry 2002, 4.15.1–4.15.21) (2′F-ANA) has encouraged our research group to optimize the synthetic procedures for 2′-deoxy-2′-fluoro-β-D-arabinonucleosides (araF-N). The synthesis of araF-U, araF-T, araF-A and araF-C is straightforward, (Tann, C.H.; Brodfuehrer, P.R.; Brundidge, S.P.; Sapino, C., Jr. Howell H.G. Fluorocarbohydrates in synthesis. An efficient synthesis of 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-iodouracil (β-FIAU) and 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)thymine (β-FMAU). J. Org. Chem. 1985, 50, 3644–3647; Howell, H.G.; Brodfuehrer, P.R.; Brundidge, S.P.; Benigni, D.A.; Sapino, C., Jr. Antiviral nucleosides. A stereospecific, total synthesis of 2′-fluoro-2′-deoxy-β-D-arabinofuranosyl nucleosides. J. Org. Chem. 1988, 53, 85–88; Maruyama, T.; Takamatsu, S.; Kozai, S.; Satoh, Y.; Izana, K. Synthesis of 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine bearing a selectively removable protecting group. Chem. Pharm. Bull. 1999, 47, 966–970) however, the synthesis of the guanine analogue is more complicated and affords poor to moderate yields of araF-G (4) ((a) Elzagheid, M.I.; Viazovkina, E.; Masad, M.J. Synthesis of protected 2′-deoxy-2′-fluoro-β-D-arabinonucleosides. Synthesis of 2′-fluoroarabino nucleoside phosphoramidites and their use in the synthesis of 2′F-ANA. Current Protocols in Nucleic Acid Chemistry 2002, 1.7.1–1.7.19; (b) Tennila, T.; Azhayeva, E.; Vepsalainen, J.; Laatikainen, R.; Azhayev, A.; Mikhailopulo, I. Oligonucleotides containing 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-adenine and -guanine: synthesis, hybridization and antisense properties. Nucleosides, Nucleotides and Nucl. Acids 2000, 19, 1861–1884). Here we describe an efficient synthesis of araF-G (4) that involves coupling of 2-deoxy-2-fluoro-3,5-di-O-benzoyl-α-D- arabinofuranosyl bromide (1) with 2-chlorohypoxanthine (2) to afford 2-chloro-β-araF-I (3) in 52% yield. Nucleoside (3) was transformed into araF-G (4) by treatment with methanolic ammonia (150°C, 6 h) in 67% yield.     

Improved and Reliable Synthesis of 3′‐Azido‐2′,3′‐dideoxyguanosine Derivatives

An improved synthesis of N²‐protected‐3′‐azido‐2′,3′‐dideoxyguanosine 20 and 23 is described. Deoxygenation of 2′‐O‐alkyl (and/or aryl) sulfonyl‐5′‐dimethoxytritylguanosine coupled with [1,2]‐hydride shift rearrangement gave protected 9‐(2‐deoxy‐threo‐pentofuranosyl)guanines ( 10 , 12 and 16 ). This rearrangement was accomplished in high yield with a high degree of stereoselectivity using lithium triisobutylborohydride (l‐Selectride®). Compounds 10 , 12 and 16 were transformed into 3′‐O‐mesylates ( 18 and 21 ), which can be used for 3′‐substitution. The 3′‐azido nucleosides were obtained by treatment of 18 and 21 with lithium azide. This procedure is reproducible with a good overall yield.