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Expanding the Genetic Alphabet: Non-epimerizing Nucleoside with the PyDDA Hydrogen-bonding Pattern

Overview
Journal J Org Chem
Publisher American Chemical Society
Specialty Chemistry
Date 2003 Dec 6
PMID 14656120
Citations 17
Authors
Daniel Hutter
Steven A Benner
Affiliations
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Abstract

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.

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