Volume 28, Issue 50
Natural Products
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ChemInform Abstract: Preparation of Fluorinated Galactosyl Nucleoside Diphosphates to Study the Mechanism of the Enzyme Galactopyranose Mutase.

A. BURTON

A. BURTON

Sch. Chem., Univ. Birmingham, Edgbaston, Birmingham B15 2TT, UK

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P. WYATT

P. WYATT

Sch. Chem., Univ. Birmingham, Edgbaston, Birmingham B15 2TT, UK

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G.-J. BOONS

G.-J. BOONS

Sch. Chem., Univ. Birmingham, Edgbaston, Birmingham B15 2TT, UK

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First published: 02 August 2010

Abstract

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ChemInform Abstract

The synthesis of two fluorinated galactosyl nucleoside diphosphates ( VIII) and (IX) using a novel latent → active phosphorylation strategy based on the isomerization of substituted allyl to vinyl glycoside (cf. (II) → (III)) and subsequent phosphorylation with dibenzyl hydrogenphosphate (IV) is given. Both synthesized diphosphates do not inhibit the enzyme galactopyranose mutase in the direction pyranose → furanose but both compounds inhibit the reverse reaction.

chemical structure image

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