共查询到20条相似文献,搜索用时 7 毫秒
1.
Mitsuo Sekine Osamu Kurasawa Kohji Seio Koh-Ichiroh Shohda Takeshi Wada 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):1163-1168
Abstract This paper describes the design and synthesis of a conformationally rigid dimer building block Umpc3Um having a propylene bridge linked between the uracil 5-position and 5′-phosphate group of pUm. Oligonucleotides incorporating the dimer unit with either the Sp or Rp configuration were synthesized by use of the phosphoramidite approach. The conformational properties of the dimer units and these oligonucleotides were studied in detail. 相似文献
2.
Abstract The synthesis of several new 5′-deoxy-5′-nucleosideacetic acid derivatives by the reactions of alkoxycarbonylmethylene triphenylphosphoranes with nucleoside 5′-aldehydes is described. 相似文献
3.
José Fiandor María Teresa García-López Federico G. De las Heras 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1325-1334
Abstract Reaction of 3-N-benzyl-5′-deoxy-5′-haloderivatives of uridine with the carbanions derived from diethyl malonate, ethyl acetoacetate, ethyl cyanoacetate and malondinitrile afforded the corresponding highly functionalized 5′-C-chain-extended uridines. 相似文献
4.
Ramon Eritja Victor E. Marquez Ramon Güimil García 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1111-1114
Abstract The preparation of a protected derivative of 5-aza-2′-deoxycytidine carrying the 2-(p-nitrophenyl)ethyl group is described. The new derivative is useful for the preparation of oligonucleotides containing 5-aza-2′-deoxycytidine using a special methodology that avoids the use of ammonia. 相似文献
5.
Tomas Szabó Annika Kers Jacek Stawinski 《Nucleosides, nucleotides & nucleic acids》2013,32(3-5):871-874
Abstract A new approach to the solid phase synthesis of 5′-methylenephosphonate DNA is described. It makes use of intramolecular catalysis which ensures rapid and high-yielding condensations and thus provides a convenient entry to ionic, achiral analogs of thymidylic acids up to 20 nucleotides in length. 相似文献
6.
Bruce S. Ross Guillermo Vasquez Sheri Manalili Elena Lesnik Richard Griffey 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1547-1549
Abstract A short multigram synthesis of 2′-O-methylpseudouridine and its phosphoramidite derivative is described which avoids the use of protecting groups on the nitrogens. A binding study of oligonucleotides containing this modification suggest an increased binding affinity to RNA when compared to oligonucleotides incorporating 2′-O-methyluridine. 相似文献
7.
Laureen C. Colis Debasis Chakraborti Pablo Hilario Christopher McCarty Ashis K. Basu 《Nucleosides, nucleotides & nucleic acids》2013,32(2):67-77
Two different approaches to synthesize oligonucleotides containing the 2 ′-deoxyguanosine adducts formed by nitropyrenes are described. A direct reaction of an unmodified oligonucleotide with an activated nitropyrene derivative is a convenient biomimetic approach for generating the major adducts in DNA. A total synthetic approach, by contrast, involves several synthetic steps, including Buchwald-Hartwig Pd-catalyzed coupling, but can be used for incorporating both the major and minor adducts in DNA in high yield. 相似文献
8.
Novel 4′-cyclopropyl-5′-norcarbocyclic adenosine phosphonic acid analogues were designed and racemically synthesized from propionaldehyde 5 through a de novo acyclic stereoselective route using triple Grignard addition and ring-closing metathesis (RCM) as key reactions. To improve cellular permeability and enhance the anti-HIV activity of this phosphonic acid, SATE phosphonodiester nucleoside prodrug 23 was prepared. The synthesized adenosine phosphonic acids analogues 17, 18, 19, 21, and 23 were subjected to antiviral screening against HIV-1. Compound 23 exhibits enhanced anti-HIV activity than its parent nucleoside phosphonic acid 18. 相似文献
9.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1073-1075
Abstract 5-Carboxy-2′-deoxyuridine is a methyl oxidation product of thymidine. It can be formed by the menadione-mediated photosensitization of thymidine in aerated aqueous solution. Here in we present a new four-step synthesis of the 5-carboxy-2′-deoxyuridine phosphoramidite building block based on the alkaline hydrolysis of 5-trifluoromethyl-2′-deoxyuridine. The phosphoramidite derivative has been incorporated at defined sites into oligonucleotides using the solid phase synthesis approach. 相似文献
10.
Darya S. Novopashina Olesya S. Totskaya Maria I. Meschaninova Dmitry A. Stetsenko Alya G. Venyaminova 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):821-825
We have developed a new method for the preparation of oligodeoxyribonucleotides and oligo(2′-O-methylribonucleotides) that contain a 2′-phosphorylated ribonucleoside residue, and optimized it to avoid 2′ -3′ -isomerization and chain cleavage. Structures of the 2′ -phosphorylated oligonucleotides were confirmed by MALDI-TOF MS and enzymatic digestion, and the stability of their duplexes with DNA and RNA was investigated. 2′-Phosphorylated oligonucleotides may be useful intermediates for the introduction of various chemical groups for a wide range of applications. 相似文献
11.
Ryszard Kierzek Wojciech T. Markiewicz 《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):403-405
Abstract 5′3′-O-protected 4-N-tosyl-2′-deoxycyt id ine was converted with 1,6-diaminohexane to 4-N-/6-ami nohexyl/-2′-deoxycyt id i ne and then into 5′-0-d imethoxytr i ty 1 -k-N-/(-tr if luoroacetamidohexyl 1–2 ′-deoxycyt id ine, The latter was used to prepare oligonucleotides by the phosphoramidite approach. Deprotected oligomers were labeled with biotin. 相似文献
12.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1383-1385
Abstract Oligonucleotides carrying 2′-aldehyde groups were synthesized and coupled to peptides containing an N-terminal cysteine, aminooxy or hydrazide group to give peptide-oligonucleotide conjugates in good yield. The synthesis of a novel phosphoramidite reagent for the incorporation of 2′-O-(2,3-diaminopropyl)uridine into oligonucleotides was also described. Resultant 2′-diaminooligonucleotides may be useful intermediates in further peptide conjugation studies. 相似文献
13.
Ekambar R. Kandimalla Jamal Temsamani Sudhir Agrawal 《Nucleosides, nucleotides & nucleic acids》2013,32(3-5):1031-1035
Abstract 2′-O-methylribonucleoside methylphosphonamidites are synthesized and incorporated into oligonucleotides to obtain chimeric antisense oligonucleotides. The resulting oligonucleotide binds to their target RNA/DNA sequences efficiently and stable in a medium containing bovine serum. 相似文献
14.
Vladimir V. Tolstikov Dmitry A. Stetsenko Victor K. Potapov Eugene D. Sverdlov 《Nucleosides, nucleotides & nucleic acids》2013,32(3):215-225
Abstract 5′-Dimethoxytrityl-5-(3-methoxypropynyl)-2′-deoxyuridine phosphoroamidite was synthesized with the use of commercial 3- methoxypropyne. Oligonucleotides (ODNs) containing 5-(3- ethoxypropynyl)- 2′-deoxyuridine in different positions were prepared. The stabilities of the duplexes formed by these ODNs with the complementary templates are increased in comparison with the unmodified counterparts. On average modified residue incorporated, the Tm is raised by 1°C. 相似文献
15.
Caryn Evilia Xiaolin Zhang Jean Kanyo Ponzy Lu 《Nucleosides, nucleotides & nucleic acids》2013,32(10-11):1809-1820
Abstract A method to convert 5-FdU phosphoramidite to 4-triazol-5- FdU phosphoramidite was used to make deoxyoligonucleotides containing 5- FdC to follow a rare transition between a tandem hairpin and a single hairpin form, which results in moving a distant 5-FdC, 5-FdU bases into juxtaposition. 相似文献
16.
Ajay Kumar 《Nucleosides, nucleotides & nucleic acids》2013,32(5):441-447
Abstract A novel method for the synthesis of oligonucleotides with terminal-3′-phosphate using universal CPG polymer support is described. 相似文献
17.
Novel 5′-deoxycarbocyclic purine phosphonic acid analogs with the 4′-electropositive moiety, fluorine were designed, and synthesized from glyceraldehyde. The cyclopentenol intermediate, 9, was successfully synthesized by the ring-closing metathesis of divinyl 8. The condensation reaction of cyclopentanol 15 with purine bases under Mitsunobu conditions successfully afforded the desired phosphonate analogs. The synthesized nucleoside phosphonic acid analogs, 19, 22, 26, and 29, were subjected to antiviral screening against human immunodeficiency virus (HIV)-1. Guanine phosphonic acid analog 29 showed significant anti-HIV activity (EC50 = 10.3 μM). 相似文献
18.
V. Petyuk M. Zenkova R. Giege V. Vlassov 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):1459-1461
Abstract Interaction of yeast tRNAPhe with oligodeoxyribonucleotides (ONs), complementary to the nucleotides 62–76 was investigated. Results of gel-mobility shift assay and RNase A probing evidence that the ONs containing the sequence complementary to the tRNA ACCA end can easily invade the hairpin structure under physiological conditions. The limiting step of association process is the tRNA unfolding. 相似文献
19.
Natalya Ramzaeva Helmut Rosemeyer Frank Seela 《Nucleosides, nucleotides & nucleic acids》2013,32(3-5):947-950
Abstract The rate and velocity of the photoconversion of 2-chloro-2′-deoxyadenosine into 2′-deoxyisoguanosine within oligonucleotides was found to be sequence-specific and depends on the nearest neighbor. 相似文献
20.
María-José Camarasa Federico G. De las Heras María Jesús Pérez-Pérez 《Nucleosides, nucleotides & nucleic acids》2013,32(4):533-546
Abstract Reaction of 3′-0-(t-butyldimethylsilyl)-2′-deoxythymidine-5′-carboxaldehyde and 2′,3′-dideoxythymidine-5′-carboxaldehyde with acetone afforded a 3:2 mixture of the two (5′R)- and (5′S)-5′-acetonylthymidine derivatives. 相似文献