Communication

From Disulfide‐ to Thioether‐Linked Glycoproteins^†

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Elizabeth J. Grayson Dr.

Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK

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Sam Thompson

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Justin M. Chalker

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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James C. Errey Dr.

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Farid El Oualid Dr.

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Timothy D. W. Claridge Dr.

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Benjamin G. Davis Prof.

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Gonçalo J. L. Bernardes

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Elizabeth J. Grayson Dr.

Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK

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Sam Thompson

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Justin M. Chalker

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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James C. Errey Dr.

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Farid El Oualid Dr.

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Timothy D. W. Claridge Dr.

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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Benjamin G. Davis Prof.

Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865‐285002

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First published: 03 March 2008

https://doi.org/10.1002/anie.200704381

Citations: 89

^†

We thank the Fundação para a Ciência e a Tecnologia, Portugal (G.J.L.B.), the Rhodes Trust (J.M.C), and the European Commission (F.E.O.) for financial support and the Daphne Jackson Trust for a returner's fellowship funded by the Royal Commission for the Exhibition of 1851 (E.J.G.).

Abstract

Strengthening the bond: The introduction of a thiol tag in combination with chemoselective ligation to form a disulfide‐linked bioconjugate is a selective and useful method for site‐selective protein glycosylation. The phosphine‐mediated desulfurization of such glycoconjugates to their reductant‐resistant thioether‐linked counterparts completes a convergent, site‐selective synthesis of thioether‐linked glycoproteins (see scheme).