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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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Publication details

The article was received on 06 Oct 2012, accepted on 24 Oct 2012 and first published on 24 Oct 2012


Article type: Communication
DOI: 10.1039/C2CC37305J
Citation: Chem. Commun., 2012,48, 11987-11989
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    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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