De novochemoenzymatic synthesis of sialic acid

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 alpha -keto- gamma...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2012-11, Vol.48 (98), p.11987-11989
Main Authors: Stallforth, Pierre, Matthies, Stefan, Adibekian, Alexander, Gillingham, Dennis G, Hilvert, Donald, Seeberger, Peter H
Format: Article
Language:English
Subjects:
Aldehydes
Signatures
Strategy
Synthesis
Online Access:Get full text
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Summary: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 alpha -keto- gamma -hydroxy acid moiety with high diastereoselectivity.
ISSN:1359-7345
1364-548X
DOI:10.1039/c2cc37305j