Communication

A Coordinated Synthesis and Conjugation Strategy for the Preparation of Homogeneous Glycoconjugate Vaccine Candidates^†

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

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149

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Justin M. Chalker

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149

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Dr. Omar Boutureira

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149

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Dr. Julia R. Koeppe

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149

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Prof. Benjamin G. Davis

Corresponding Author

E-mail address: ben.davis@chem.ox.ac.uk

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149 Search for more papers by this author

Dr. Elizabeth J. Grayson

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

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Dr. Gonçalo J. L. Bernardes

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149

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Justin M. Chalker

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149

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Dr. Omar Boutureira

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149

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Dr. Julia R. Koeppe

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149

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Prof. Benjamin G. Davis

Corresponding Author

E-mail address: ben.davis@chem.ox.ac.uk

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA (UK), Fax: (+44) 1865‐285‐002 http://users.ox.ac.uk/∼dplb0149

First published: 31 March 2011

https://doi.org/10.1002/anie.201006327

Citations: 52

^†

We gratefully acknowledge the Leverhulme Trust (E.J.G.), FCT and Gulbenkian, Portugal (G.J.L.B.), The Rhodes Trust and the National Science Foundation (J.M.C.), EC (Marie Curie IEF, O.B.), and The International AIDS Vaccine Initiative (J.R.K., G.J.L.B.) for financial support. We thank Prof. M. G. Finn for kindly providing p75m/Qβ plasmid. B.G.D. is a Royal Society Wolfson Research Merit Award recipient.

Abstract

A sweet solution: A strategy for the synthesis of well‐defined carbohydrate‐based vaccines is presented. The approach couples complex oligosaccharide synthesis to site‐specific conjugation methodology to provide pure glycoprotein vaccine candidates (see scheme).