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Synthesis of the complete series of mono acetates of N-acetyl-d-neuraminic acid†
Paul A. Clarke,Nimesh Mistry,Gavin H. Thomas
Organic & Biomolecular Chemistry Pub Date : 10/03/2011 00:00:00 , DOI:10.1039/C1OB06348K
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
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