Literature DB >> 14656120

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

Daniel Hutter1, Steven A Benner.   

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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Year:  2003        PMID： 14656120     DOI： 10.1021/jo034900k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  12 in total

1.  Structural basis for a six nucleotide genetic alphabet.

Authors:  Millie M Georgiadis; Isha Singh; Whitney F Kellett; Shuichi Hoshika; Steven A Benner; Nigel G J Richards
Journal:  J Am Chem Soc       Date:  2015-05-18       Impact factor: 15.419

2.  Synthesis and antibacterial evaluation of new N- and S-glycosides analogues with dinitrophenyl-substituted heterocyclic bases.

Authors:  Fatima Belkhadem; Adil A Othman
Journal:  Mol Divers       Date:  2016-10-19       Impact factor: 2.943

3.  Amplification, mutation, and sequencing of a six-letter synthetic genetic system.

Authors:  Zunyi Yang; Fei Chen; J Brian Alvarado; Steven A Benner
Journal:  J Am Chem Soc       Date:  2011-09-06       Impact factor: 15.419

Review 4.  Cell-free biology: exploiting the interface between synthetic biology and synthetic chemistry.

Authors:  D Calvin Harris; Michael C Jewett
Journal:  Curr Opin Biotechnol       Date:  2012-04-04       Impact factor: 9.740

5.  2'-deoxy-1-methylpseudocytidine, a stable analog of 2'-deoxy-5-methylisocytidine.

Authors:  Hyo-Joong Kim; Nicole A Leal; Steven A Benner
Journal:  Bioorg Med Chem       Date:  2009-03-27       Impact factor: 3.641

Review 6.  The expanded genetic alphabet.

Authors:  Denis A Malyshev; Floyd E Romesberg
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-25       Impact factor: 15.336

7.  Investigation of the DNA-dependent cyclohexenyl nucleic acid polymerization and the cyclohexenyl nucleic acid-dependent DNA polymerization.

Authors:  Veerle Kempeneers; Marleen Renders; Matheus Froeyen; Piet Herdewijn
Journal:  Nucleic Acids Res       Date:  2005-07-12       Impact factor: 16.971

8.  Triplex-forming properties and enzymatic incorporation of a base-modified nucleotide capable of duplex DNA recognition at neutral pH.

Authors:  David A Rusling
Journal:  Nucleic Acids Res       Date:  2021-07-21       Impact factor: 16.971

9.  Artificially expanded genetic information system: a new base pair with an alternative hydrogen bonding pattern.

Authors:  Zunyi Yang; Daniel Hutter; Pinpin Sheng; A Michael Sismour; Steven A Benner
Journal:  Nucleic Acids Res       Date:  2006-10-29       Impact factor: 16.971

10.  Enzymatic incorporation of a third nucleobase pair.

Authors:  Zunyi Yang; A Michael Sismour; Pinpin Sheng; Nyssa L Puskar; Steven A Benner
Journal:  Nucleic Acids Res       Date:  2007-06-18       Impact factor: 16.971
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