Communication

The Direct Formation of Glycosyl Thiols from Reducing Sugars Allows One‐Pot Protein Glycoconjugation^†

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 1865‐275‐652

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David P. Gamblin Dr.

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 1865‐275‐652

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Benjamin G. Davis Dr.

E-mail address: Ben.Davis@chem.ox.ac.uk

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 1865‐275‐652

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Gonçalo J. L. Bernardes

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 1865‐275‐652

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David P. Gamblin Dr.

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 1865‐275‐652

Search for more papers by this author

Benjamin G. Davis Dr.

E-mail address: Ben.Davis@chem.ox.ac.uk

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK, Fax: (+44) 1865‐275‐652

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First published: 01 June 2006

https://doi.org/10.1002/anie.200600685

Citations: 92

^†

We gratefully acknowledge the Fundação para a Ciência e a Tecnologia, Portugal for the award of a doctoral fellowship (G.J.L.B., grant BD/16997/2004), and the EPRSC (D.P.G.). We also thank Katie J. Doores and Dr. Graeme Horne for helpful discussions, and Alister French and Norberto Reis for graphics.

Abstract

Sweet and easy: A one‐pot method consisting of direct thionation (1) followed by thiol‐mediated chemoselective ligation (2) can be used for site‐selective protein glycosylation. This procedure, which uses the Lawesson reagent, has been shown to be fully compatible with unprotected sugars, the products of which can be directly used in a selenenylsulfide protein glycosylation strategy.