Unit

UNIT 13.7 Stereoselective Synthesis of Sugar Nucleotides Using Neighboring Group Participation

  1. Shannon C. Timmons,
  2. David L. Jakeman

Published Online: 1 DEC 2007

DOI: 10.1002/0471142700.nc1307s31

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Timmons, S. C. and Jakeman, D. L. 2007. Stereoselective Synthesis of Sugar Nucleotides Using Neighboring Group Participation. Current Protocols in Nucleic Acid Chemistry. 31:13.7:13.7.1–13.7.16.

Author Information

  1. Dalhousie University, Halifax, Nova Scotia, Canada

Publication History

  1. Published Online: 1 DEC 2007
  2. Published Print: DEC 2007

Abstract

A straightforward, efficient method for the chemical synthesis of sugar nucleotides derived from d-mannose and l-fucose precursors is described. This synthetic strategy involves the coupling of acylated glycosyl bromides with nucleoside 5′-diphosphates, which enables the exploitation of neighboring group participation to exclusively prepare diastereomerically pure sugar nucleotides of desired 1,2-trans anomeric configuration. This is the first stereoselective direct coupling approach to sugar nucleotide synthesis. Following deprotection using triethylamine and purification via C18 reversed-phase ion-pair chromatography, UDP- and GDP-α-d-mannose as well as UDP- and GDP-β-l-fucose were obtained in good yield in only four synthetic steps from d-mannose and l-fucose. Curr. Protoc. Nucleic Acid Chem. 31:13.7.1-13.7.16. © 2007 by John Wiley & Sons, Inc.

Keywords:

  • sugar nucleotides;
  • glycosylation;
  • glycosyl bromides;
  • nucleoside 5′-diphosphates;
  • neighboring group participation;
  • glycosyltransferases;
  • oligosaccharides;
  • glycoconjugates