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Issue 98, 2012
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De novo chemoenzymatic synthesis of sialic acid

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Abstract

A chemoenzymatic synthesis of sialic acid from inexpensive N-acetyl-D-glucosamine is described. In a three-step Wittig–protection–ozonolysis strategy manno-configured aldehydes are obtained. Treatment with oxaloacetate in the presence of macrophomate synthase affords the signature α-keto-γ-hydroxy acid moiety with high diastereoselectivity.

Graphical abstract: De novo chemoenzymatic synthesis of sialic acid

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Article information


Submitted
06 Oct 2012
Accepted
24 Oct 2012
First published
24 Oct 2012

Chem. Commun., 2012,48, 11987-11989
Article type
Communication

De novo chemoenzymatic synthesis of sialic acid

P. Stallforth, S. Matthies, A. Adibekian, D. G. Gillingham, D. Hilvert and P. H. Seeberger, Chem. Commun., 2012, 48, 11987
DOI: 10.1039/C2CC37305J

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