Issue 98, 2012
From the journal:

Chemical Communications

De novo chemoenzymatic synthesis of sialic acid†

Pierre Stallforth,‡§a   Stefan Matthies,§a   Alexander Adibekian,a   Dennis G. Gillingham,||b   Donald Hilvertb  and  Peter H. Seeberger*a  

* Corresponding authors

a Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam-Golm, Germany and Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany
E-mail: peter.seeberger@mpikg.mpg.de
Fax: +49 331 567 9302
Tel: +49 331 567 9301

b Laboratory of Organic Chemistry, ETH Zurich, 8093 Zurich, Switzerland

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

DOI
https://doi.org/10.1039/C2CC37305J
Article type
Communication
Submitted
06 Oct 2012
Accepted
24 Oct 2012
First published
24 Oct 2012

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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