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.
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页码：9839 / 9842
页数：4
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