Jump to main content
Jump to site search

Issue 3, 2012
Previous Article Next Article

Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid

Author affiliations

Abstract

The short syntheses of each of the mono-acetates of N-acetyl-D-neuraminic acid are reported. These are important molecules for studying the mechanism and function of enzymes which utilise Neu5Ac as a substrate. However, until now these molecules were not available as pure compounds and instead had to be studied as mixtures. Neu4,5Ac2 and Neu5,8Ac2 were synthesised from a common precursor in 2 and 4 steps respectively, while Neu2,4Ac2 and Neu5,7Ac2 were synthesised in 3 and 4 steps respectively from another common precursor. Both precursors could be easily prepared in 3 steps from Neu5Ac itself. Importantly, no scrambling of the anomeric stereochemistry was detected throughout the course of these syntheses.

Graphical abstract: Synthesis of the complete series of mono acetates of N-acetyl-d-neuraminic acid

Back to tab navigation

Supplementary files

Publication details

The article was received on 08 Aug 2011, accepted on 30 Sep 2011 and first published on 03 Oct 2011


Article type: Paper
DOI: 10.1039/C1OB06348K
Citation: Org. Biomol. Chem., 2012,10, 529-535
  •   Request permissions

    Synthesis of the complete series of mono acetates of N-acetyl-D-neuraminic acid

    P. A. Clarke, N. Mistry and G. H. Thomas, Org. Biomol. Chem., 2012, 10, 529
    DOI: 10.1039/C1OB06348K

Search articles by author

Spotlight

Advertisements