Parasite glycoconjugates. Part 12. Synthesis of deoxy, fluorodeoxy and aminodeoxy disaccharide phosphates, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania

Dmitry V. Yashunsky; Yury E. Tsvetkov; Michael A. J. Ferguson; Andrei V. Nikolaev

doi:10.1039/B106182H

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Parasite glycoconjugates. Part 12.¹ Synthesis of deoxy, fluorodeoxy and aminodeoxy disaccharide phosphates, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania

Dmitry V. Yashunsky,^a Yury E. Tsvetkov,^a Michael A. J. Ferguson^b and Andrei V. Nikolaev*^a

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* Corresponding authors

^a Carnelley Building, School of Life Sciences (Chemistry), University of Dundee, Dundee, UK

^b Wellcome Trust Building, School of Life Sciences (Biochemistry), University of Dundee, Dundee, UK

Abstract

A set of phosphodisaccharides, structural analogues of the β-D-galactosyl-(1→4)-α-D-mannosyl phosphate 1, are synthesized using the Koenigs–Knorr method for the glycosylation reactions and the glycosyl hydrogenphosphonate method for phosphorylation. The compounds were tested as acceptor substrates/putative inhibitors for the Leishmania α-D-mannosylphosphate transferase.

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Article information

DOI: https://doi.org/10.1039/B106182H
Article type: Paper
Submitted: 12 Jul 2001
Accepted: 20 Nov 2001
First published: 21 Dec 2001

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J. Chem. Soc., Perkin Trans. 1, 2002, 242-256

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Parasite glycoconjugates. Part 12. Synthesis of deoxy, fluorodeoxy and aminodeoxy disaccharide phosphates, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania

D. V. Yashunsky, Y. E. Tsvetkov, M. A. J. Ferguson and A. V. Nikolaev, J. Chem. Soc., Perkin Trans. 1, 2002, 242 DOI: 10.1039/B106182H

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Journal of the Chemical Society, Perkin Transactions 1