扩展遗传字母表：具有pyDDA氢键模式的非差向异构化核苷。
Expanding the genetic alphabet: non-epimerizing nucleoside with the pyDDA hydrogen-bonding pattern.
作者信息
Hutter Daniel, Benner Steven A
机构信息
Department of Chemistry and Department of Anatomy and Cell Biology, University of Florida, Gainesville, Florida 32611-7200
出版信息
J Org Chem. 2003 Dec 12;68(25):9839-42. doi: 10.1021/jo034900k.
6-Amino-3-(2'-deoxy-beta-D-ribofuranosyl)-5-nitro-1H-pyridin-2-one (4), a C-glycoside exhibiting the nonstandard pyDDA 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.
6-氨基-3-(2'-脱氧-β-D-呋喃核糖基)-5-硝基-1H-吡啶-2-酮(4)是一种具有非标准pyDDA氢键模式的C-糖苷，通过Heck偶联反应合成。硝基极大地增强了核苷对酸催化差向异构化的稳定性，而不会导致在生理pH值下杂环发生明显的去质子化。这些结果使核苷4成为扩展遗传字母表的一个有前景的候选物。
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