A convenient synthesis of nucleoside diphosphate glycopyranoses and other polyphosphorylated bioconjugates

Saskia Wolf; Tanja Zismann; Nathalie Lunau; Svenja Warnecke; Silke Wendicke; Chris Meier

doi:10.1016/j.ejcb.2009.10.013

A convenient synthesis of nucleoside diphosphate glycopyranoses and other polyphosphorylated bioconjugates

Eur J Cell Biol. 2010 Jan;89(1):63-75. doi: 10.1016/j.ejcb.2009.10.013. Epub 2009 Dec 31.

Authors

Saskia Wolf¹, Tanja Zismann, Nathalie Lunau, Svenja Warnecke, Silke Wendicke, Chris Meier

Affiliation

¹ Institute of Organic Chemistry, Department of Chemistry, Faculty of Sciences, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.

PMID: 20045214
DOI: 10.1016/j.ejcb.2009.10.013

Abstract

In this review, we summarize results obtained using a conceptionally new chemical synthesis of NDP-sugars based on cycloSaligenyl (cycloSal) nucleotides as starting material (cycloSal technique). The cycloSal technique not only leads to stereoisomerically defined NDP-sugars in high yield, but the same principle provides very efficient routes towards nucleoside di- and -triphosphates. Moreover, sugar-nucleotides such as CMP-Neu5Ac and dinucleoside polyphosphates are available. Thus, the method offers a nearly universal chemical access towards a large number of highly interesting bioconjugates and biomolecules.

Publication types

Research Support, Non-U.S. Gov't
Review

MeSH terms

Biochemistry / methods*
Glycoconjugates / chemical synthesis*
Glycoconjugates / chemistry
Nucleoside Diphosphate Sugars / chemical synthesis*
Nucleoside Diphosphate Sugars / chemistry
Phosphorylation

Substances

Glycoconjugates
Nucleoside Diphosphate Sugars