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1.
Abstract 2′ -Deoxy-3-isoadenylyl(3′-5′)thymidine and thymidylyl-(3′-5′)-2′-deoxy-3-isoadenosine have been synthesized by mild protection/deprotection methodology that circumvents facile N3-Cl′ hydrolytic cleavage of the 2′-deoxy-3-isoadenosine moiety. 相似文献
2.
Purshotam Bhan Anila Bhan Mikung Hong John G. Hartwell June M. Saunders Glenn D. Hoke 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1195-1199
Abstract ABSTRACT: 3′-Deoxy-(2′-5′) oligonucleotides bind selectively to complementary RNA but not to DNA. 3′-Deoxy-(2′-5′) phosphorothioate ODN chimeras embedded with a short stretch of 3′-5′ phosphorothioate cassette are potent inhibitors of steroid 5-α-reductasc expression with significantly less non-specific interactions in cell culture. 相似文献
3.
Abstract The solid-phase preparation of oligodeoxyribonucleotides covalently linked via nucleic bases with normal (3′-5′) or inverted (5′-5′) polarities is reported. The key-step of these syntheses is the preparation of the tethered dimers. 相似文献
4.
Akira Matsuda Hitomi Okajima Akira Masuda Akio Kakefuda Yuichi Yoshimura Tohru Ueda 《Nucleosides, nucleotides & nucleic acids》2013,32(2-4):197-226
Abstract New methods for the synthesis of 2′,3′-didehydro-2′,3′-dideoxy-2′ (and 3′)-methyl-5-methyluridines and 2′,3′-dideoxy-2′ (and 3′)-methylidene pyrimidine nucleosides have been developed from the corresponding 2′ (and 3′)-deoxy-2′ (and 3′)-methylidene pyrimidine nucleosides. Treatment of a 3′-deoxy-3′-methylidene-5-methyluridine derivative 8 with 1,1′-thiocarbonyldiimidazole gave the allylic rearranged 2′,3′-didehydro-2′,3′-dideoxy-3′-[(imidazol-1-yl)carbonylthiomethyl] derivative 24. On the other hand, reaction of 8 with methyloxalyl chloride afforded 2′-O-methyloxalyl ester 25. Radical deoxygenation of both 24 and 25 gave 26 exclusively. Palladium-catalyzed reduction of 2′,5′-di-O-acetyl-3′-deoxy-3′-methylidene-5-methyluridine (32) with triethylammonium formate as a hydride donor regioselectively afforded the 2′,3′-dideoxy-3′-methylidene derivative 35 and 2′,3′-didehydro-2′,3′-dideoxy-3′-methyl derivative 34 in a ratio of 95:5 in 78% yield. These reactions were used on the corresponding 2′-deoxy-2′-methylidene derivatives. An alternative synthesis of 2′,3′-dideoxy-2′-methylidene pyrimidine nucleosides (43, 52, and 54) was achieved from the corresponding 1-(3-deoxy-β-D-thero-pentofuranosyl)pyrimidines (44 and 45). The cytotoxicity against L1210 and KB cells and inhibitory activity of the pathogenicity of HIV-1 are also described 相似文献
5.
Masako Muraoka Akiko Iida Seizo Takahashi Tomohiko Ebata Seiichi Uesugi 《Nucleosides, nucleotides & nucleic acids》2013,32(6):1317-1332
Abstract Self complementary diribonucleoside monophosphates containing 2-aminoadenosine (n2A) and uridine (U) residues, (2′-5′) n2ApU (1), (3′-5′) n2ApU (2), (2′-5′) Upn2A (3) and (3′-5′) Upn2A (4), were synthesized by condensation of suitably protected nucleoside and nucleotide units using dicyclohexylcarbodiimide (DCC). The dimers, (3) and (41, were also obtained from uridine 2′,3′-cyclic phosphate and unprotected 2-aminoadenosine using 2,4,6-triisopropylbenzenesulfonyl chloride (TPS-Cl) as the condensing agent. The conformational properties of these dimers were examined by UV, CD and NMR spectroscopy. The results reveal that the 2′-5′ isomers take a stacked conformation, which contains a larger base-base overlap and is more stable against thermal perturbation with respect to the 3′-5′ isomers. The n2ApU isomers have more stacked structure than the Upn2A isomers. 相似文献
6.
M. Nemer N. Thëriault A. Schifman K. K. Ogilvie 《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):257-258
Abstract Several symmetrically linked (3′-3′, 2′-2’ and 5′-5′) diribonucleoside monophosphates were prepared using the phosphodichloridite procedure. The 3′-3’ and 2′-2’ dimers showed unusual lability towards both acid and base due to the two hydroxyls adjacent to the phosphate moiety. 相似文献
7.
Jeroen C. Verheijen Ling Chen Suzanne F. Bayly Paul F. Torrence Gijsbert A. van der Marel J. H. Van Boom 《Nucleosides, nucleotides & nucleic acids》2013,32(10-12):1821-1830
Abstract Fully automated solid-phase synthesis gave access to a hybrid in which 5′-phosphorylated-2′-5′-linked oligoadenylate (2–5A) is connected to the 5′-terminus of DNA which, in turn, is linked at the 3′-end to PNA [2–5A-(5′)-DNA-(3′)-PNA chimera]. This novel antisense molecule retains full RNase L activation potency while suffering only a slight reduction in binding affinity. 相似文献
8.
Mikko Oivanen Ekaterina V. Efimtseva Sergey N. Mikhailov 《Nucleosides, nucleotides & nucleic acids》2013,32(8):1325-1331
Abstract The first-order rate constants for hydrolysis of 3′-C-methyluridylyl(2′,5′)- and -(3′,5′)adenosine and the corresponding native dinucleoside monophosphates (2′,5′- and 3′,5′-UpA) have been determined as a function of hydroxide-ion concentration (0.025 - 7 M) at 25°C. In addition to the effects on the hydrolytic stability of the compounds, the effects of the 3′-C-methyl substitution on the kinetically determined pK a values for the sugar hydroxyls of the undine moiety are discussed. 相似文献
9.
Interaction of (2′ -5′) and (3′ -5′) Linked 2-Aminoadenylyl-3-aminoadenosines with Polyuridylic Acid
Masako Muraoka Seizo Takahashi Seiichi Uesugi 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1503-1518
Abstract 2′-5′ and 3′-5′ linked 2-aminoadenylyl-2-aminoadenosines [(2′-5′)n2Apn2A (1) and (3′-5′)n2Apn2A (2)] were synthesized by condensation of 5′-O-monomethoxytrityl-N 2 N 6-dibenzoyl-2-aminoadenosine and N 2,N 6,2′,3′-O-tetrabenzoyl-2-aminoadenosine 5′-phosphate using dicyclohexylcarbodiimide (DCC). The conformational properties of these dimers 1 and 2 were examined by UV, NMR and CD spectroscopy. The results reveal that the 2′-5′-isomer 1 takes a stacked conformation, which contains a larger base-base overlap and is more stable against thermal perturbation with respect to the 3′-5′-isomer 2. Interactions of 1 and 2 with polyuridylic acid (Poly (U)) were also examined by Tm, mixing curves, UV and CD spectra. Both the dinucleoside isomers 1 and 2 formed a complex of 1 : 2 stoichiometry with poly(U), which was much more stable than that of the corresponding ApA isomer 相似文献
10.
Zbigniew J. Lesnikowski 《Nucleosides, nucleotides & nucleic acids》2013,32(9):1621-1638
Abstract An approach to the stereocontrolled synthesis of P-homochiral thiooligoribonucleotide: (Rp,Rp)- and (Sp,Sp)-diastereomers of uridinylyl′(3′, 5′)uridinylyl(3′,5′)uridine di (0,0-phosphorothioate) (9) is decribed. The influence of 2′-protection on the efficiency and stereochemistry of the coupling reaction is discussed. 相似文献
11.
Wojciech T. Markiewicz Anna Niewczyk Zofia Gdaniec Dorota A. Adamiak Zbigniew Dauter Wojciech Rypniewski 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):411-424
Abstract Minor nucleosides found in several eukaryotic initiator tRNAsi Met, O-β-D-ribofuranosyl(1″→2′)adenosine and -guanosine (Ar and Gr), as well as their pyrimidine analogues, were obtained from N-protected 3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)ribonucleosides and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose in the presence of tin tetrachloride in 1,2-dichloroethane. A crystal structure has been solved for 2′-O-ribosyluridine. The 3′-phosphoramidites of protected 2′-O-ribosylribonucleosides were prepared as the reagents for 2′-O-ribofuranosyloligonucleotides synthesis. O-β-D-Ribofuranosyl(1″→2′)adenylyl(3′→5′)guanosine (ArpG) was obtained and its structure was analysed by NMR spectroscopy. 相似文献
12.
Frank Seela Harald Debelak Hans Reuter Guide Kastner Igor A. Mikhailopulo 《Nucleosides, nucleotides & nucleic acids》2013,32(4):729-744
Abstract The 2′-O-methyl (2) and the 3′-O-methyl (3) derivatives of 1-deazaadenosine (1) were prepared. Single crystal X-ray analysis as well as 1H and 13C NMR studies were performed on the 3′-O-methyl-1-deazaadenosine 3. In the solid state, the glycosyl torsion angle (χ = 64.7°) is in the syn-range which is caused by an intramolecular (5′)CH2OH…N(3) hydrogen bond. The ribofuranose moiety adopts a 2 E (C-3′-exo; S) conformation and the orientation of the exocyclic C(4′)-C(5′) bond is + sc (γ(+)g). The conformation in solution was found to be very similar to that in solid state. Whereas the 2′-O-methyl derivative of 1 is a strong inhibitor of adenosine deaminase the 3′-O-methyl derivative is neither inhibitor nor substrate. 相似文献
13.
Abstract Two RNA sequences, AAA and AUG, were studied by the conformational search program CICADA and by molecular dynamics (MD) in the framework of the AMBER force field, and also via thorough PDB database search. CICADA was used to provide detailed information about conformers and conformational interconversions on the energy surfaces of the above molecules. Several conformational families were found for both sequences. Analysis of the results shows differences, especially between the energy of the single families, and also in flexibility and concerted conformational movement. Therefore, several MD trajectories (altogether 16 ns) were run to obtain more details about both the stability of conformers belonging to different conformational families and about the dynamics of the two systems. Results show that the trajectories strongly depend on the starting structure. When the MD start from the global minimum found by CICADA, they provide a stable run, while MD starting from another conformational family generates a trajectory where several different conformational families are visited. The results obtained by theoretical methods are compared with the thorough database search data. It is concluded that all except for the highest energy conformational families found in theoretical result also appear in experimental data. Registry numbers: adenylyl-(3′ →5′)-adenylyl-(3′ →5′)-adenosine [917-44-2] adenylyl-(3′ →5′)-uridylyl-(3′ →5′)-guanosine [3494-35-7] 相似文献
14.
Rosa Chillemi Annalinda Contino Vincenzo Cucinotta Sebastiano Sciuto 《Nucleosides, nucleotides & nucleic acids》2013,32(4):953-962
Abstract A thermodynamic and proton NMR study has been carried out in order to characterize the behaviour of 2′-deoxyadenylyl-(3′→5′)-2′-deoxyadenosine towards the protonation. Conformational changes occurring following two protonation steps are discussed. 相似文献
15.
S. H. Gray C. F. Ainsworth C. L. Bell S. S. Danyluk M. Maccoss 《Nucleosides, nucleotides & nucleic acids》2013,32(5):435-452
Abstract Two different synthetic routes using phosphotriester methodology have been utilized to prepare deoxyribonucleotidyl (3′–5′) arabinonucleosides containing 9-β-D-arabinofuranosyladenine (ara-A, vidarabine) and 1-β-D-arabinofuranosylcytosine (ara-C, cytarabine) at the 3′-terminus in amounts and purity (greater than 95%) suitable for NMR analysis. 相似文献
16.
E. Bojarska R. Kraciuk J. Wierzchowski Z. Wieczorek J. Stępiński M. Jankowska 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):1125-1126
Abstract Hydrolysis of the following four cap analogs: m7G(5′)ppp(5′)A, m7G(5′)ppp(5′)m6A, m7G(5′)ppp(5′)m2′OG and m7G(5′)ppp(5′)2′dG catalyzed by homogeneous human Fhit protein and yellow lupin Ap3A hydrolase has been investigated. The hydrolysis products were identified by HPLC analysis and the Km and Vmax values calculated based on the data obtained by the fluorimetric method. 相似文献
17.
Abstract A synthetic approach is described to obtain from AICA-riboside acyclic analogues of 2′-deoxyribosides in which the C(2′)-C(3′) bond is cleaved and the natural configuration (E) at the anomeric C (1′)-position is retained. 相似文献
18.
J. Bogan L. Ignatovich E. Stankevic 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):1183-1185
Abstract A solid-phase reversed(5′-3′) oligodeoxyribonucleotide synthesis on oxalyl and succinyl aminopropyl controlled-pore glass (CPG) is presented. Oxalyl linked oligomers are deprotected without cleavage fiom the support. 相似文献
19.
Mitsuo Sekine Kouji Seio Takahiko Satoh Kensaku Sakamoto Shigeyuki Yokoyama 《Nucleosides, nucleotides & nucleic acids》2013,32(3-4):305-321
Abstract 5-(Methylaminomethyl)uridine-containing uridylyl (3′-5′) uridine derivatives (14, 26, and 29), which were the original and modified sequences corresponding to the first letter (position 34) and the 5′-upper ribonucleoside (position 33) in the anticodon loop of minor tRNAArg, have been synthesized via 5-(methylaminomethyl)uridine derivatives (4 and 24). 相似文献
20.
Jeroen C. Verheijen Anne-Marie M. van Roon Alexander C. van der Laan Gijsbert A. van der Marel Jacques H. van Boom 《Nucleosides, nucleotides & nucleic acids》2013,32(3):493-508
Abstract The synthesis and evaluation of DNA-(3′)-PNA chimeras containing rigid linkers based on (R/S)-4-hydroxy-D/L-proline are described. It is shown that installment of the trans-L-linker using the tetrabutylammonium salt of (R)-4-(4,4′-dimethoxytrityloxy)-N-(thymin-1-yl)acetyl-L-proline (2) leads to a DNA-(3′)-PNA chimera which hybridizes efficiently with complementary RNA. 相似文献