Synthesis of beta-D-Galp-(1 - 4)-alpha-D-Manp methanephosphonate, a substrate analogue for the elongating alpha-D-mannosyl phosphate transferase in the Leishmania

An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparatio...

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Bibliographic Details
Published inTetrahedron letters Vol. 42; no. 31; pp. 5305 - 5308
Main Authors Borodkin, VS, Ferguson, MAJ, Nikolaev, AV
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 30.07.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
carbohydrates
ACCEPTOR SUBSTRATE
PHOSPHONATE
phosphonic acids and derivatives
D-MANNOPYRANOSYLPHOSPHATE TRANSFERASE
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Summary:An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/S0040-4039(01)00961-3