Expanding the genetic alphabet:: Non-epimerizing nucleoside with the pyDDA hydrogen-bonding pattern
Expanding the genetic alphabet:: Non-epimerizing nucleoside with the pyDDA hydrogen-bonding pattern
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DOI：
10.1021/jo034900k
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发表时间：
2003-12-12
影响因子：
3.6
通讯作者：
Benner, SA
中科院分区：
文献类型：
--
作者：
Hutter, D;Benner, SA
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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.