Expanding the genetic alphabet:: Non-epimerizing nucleoside with the pyDDA hydrogen-bonding pattern

被引：57

作者：

Hutter, D

Benner, SA ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

[2] Univ Florida, Dept Anat & Cell Biol, Gainesville, FL 32611 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 25期

关键词：

D O I：

10.1021/jo034900k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6-Amino-3-(2'-deoxy-beta-D-ribofuranosyl)-5-nitro-1H-pyridin-2-one (4), a C-glycoside exhibiting the nonstandard pgammaDDA hydrogen-bonding pattern, was synthesized via Heck coupling. The nitro group greatly enhances the stability of the nucleoside toward acid-catalyzed epimerization without leading to significant deprotonation of the heterocycle at physiological pH. These results make nucleoside 4 a promising candidate for an expanded genetic alphabet.

引用

页码：9839 / 9842

页数：4

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