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Ingrid Luyten RobertM. Esnouf SergeyN. Mikhailov EkaterinaV. Efimtseva Paul Michiels HansA. Heus CeesW. Hilbers Piet Herdewijn 《Helvetica chimica acta》2000,83(6):1278-1289
The solution structure of the self‐complementary deca‐ribonucleotide 5′‐r(GCGA*AUUCGC)‐3′ containing 9‐[2‐O‐(β‐D ‐ribofuranosyl)‐β‐D ‐ribofuranosyl]adenine (A*), a modified nucleotide that occurs in lower eukaryotic methionine initiator tRNAs (tRNAsiMet), was determined by NMR spectroscopy. Unexpectedly, the modification has no effect on the thermal stability of the duplex. However, the extra ribose moiety is in the C(3′)‐endo conformation and takes up a well‐defined position in the minor groove, which is in agreement with its position in tRNAsiMet as determined by X‐ray crystallography. Molecular‐dynamics simulations on the RNA duplex in H2O show that the position of the extra ribofuranose moiety seems to be stabilized by bridged H‐bonds (mediated by two H2O molecules) to the backbone of the complementary chain. 相似文献
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Edward N. Timofeev Sergey N. Mikhailov Andrei N. Zuev Ekaterina V. Efimtseva Piet Herdewijn Robert L. Somers Marc M. Lemaitre 《Helvetica chimica acta》2007,90(5):928-937
2′‐Deoxy‐1‐methyladenosine was incorporated into synthetic oligonucleotides by phosphoramidite chemistry. Chloroacetyl protecting group and controlled anhydrous deprotection conditions were used to avoid Dimroth rearrangement. Hybridization studies of intramolecular duplexes showed that introduction of a modified residue into the loop region of the oligonucleotide hairpin increases the melting temperature. It was shown that modified oligonucleotides may be easily transformed into oligonucleotides containing 2′‐deoxy‐N6‐methyladenosine. 相似文献
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G. V. Gurskaya N. E. Zhukhlistova Yu. V. Nekrasov G. V. Bobkov E. V. Efimtseva S. N. Mikhailov 《Crystallography Reports》2005,50(3):395-399
The crystal structure of a disaccharide nucleoside, 2′-O-β-D-ribopyranosylcytidine, is studied using X-ray diffraction (space group P21, a = 6.827(2) Å, b = 12.813(3) Å, c = 9.532(2) Å, β = 92.934(5)°, V = 832.7(4) Å3, Z = 2). The stereochemical features of the molecular structure of 2′-O-β-D-ribopyranosylcytidine are analyzed, and the structural data are compared with those obtained for the previously studied disaccharide nucleoside 2′-O-β-D-ribofuranosyluridine. 相似文献
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Zavgorodnii S. G. Efimtseva E. V. Mikhailov S. N. Tsilevich T. L. Yavorskii A. É. Florent'ev V. L. 《Chemistry of Heterocyclic Compounds》1988,24(2):186-191
A convenient method for the synthesis of 1,5-dihydroxy-3-oxa-2-pentyl derivatives of nucleic bases, which consists in the condensation of trimethylsilyl derivatives of nucleic bases with 1,2,5-triacetoxy-3-oxapentane in the presence of SnCl4, is proposed. Optically active derivatives — (R)- and (S)-1-(1,5-dihydroxy-3-oxa-2-pentyl)uracil, respectively — were obtained by periodate oxidation of -L- and -D-arabinopyranosyluracil.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 223–228, February, 1988. 相似文献
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EkaterinaV. Efimtseva GeorgiiV. Bobkov SergeyN. Mikhailov Arthur VanAerschot Guy Schepers Roger Busson Jef Rozenski Piet Herdewijn 《Helvetica chimica acta》2001,84(8):2387-2397
Disaccharide nucleosides with 2′‐O‐(D ‐arabinofuranosyl), 2′‐O‐(L ‐arabinofuranosyl), 2′‐O‐(D ‐ribopyranosyl), 2′‐O‐(D ‐erythrofuranosyl), and 2′‐O‐(5‐azido‐5‐deoxy‐D ‐ribofuranosyl) substituents were synthesized. These modified nucleosides were incorporated into oligonucleotides (see Table). Single substitution resulted in a ΔTm of +0.5 to −1.4° for DNA/RNA and a ΔTm of −0.8 to −4.7° for DNA/DNA duplexes. These disaccharide nucleosides can be well accommodated in RNA/DNA duplexes, and the presence of a NH2−C(5″) group has a beneficial effect on duplex stability. 相似文献
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EkaterinaV. Efimtseva AlexandraA. Shelkunova SergeyN. Mikhailov Koen Nauwelaerts Jef Rozenski Eveline Lescrinier Piet Herdewijn 《Helvetica chimica acta》2003,86(2):504-514
The efficient synthesis of O‐β‐D ‐ribofuranosyl‐(1″→2′)‐guanosine‐5″‐O‐phosphate and O‐β‐D ‐ribofuranosyl‐(1″→2′)‐adenosine‐5″‐O‐phosphate, minor tRNA components, have been developed, and their conformational properties were examined by NMR spectroscopy. 相似文献
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The glycosylation of 1,3,4-tri-O-benzoyl-2-desoxy--D-ribopyranose by bis-trimethylsilylthymine in the presence of SnCl4 and F3CS02OSiMe3 was studied. It was shown that the stereo-selectivity and directivity of the reaction are dependent on the choice of catalyst. The 1-(2-desoxy-- and -D-ribopyranosyl)-thymines obtained were converted into 3,4-seco-2-desoxythymidines.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 947–951, July, 1988.The authors wish to express their gratitude to M. Ya. Karpeiskii, S. V. Meshkov, and M. I. Struchkov for their help in the investigation. 相似文献
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