Synthesis of a library of variously modified 4-methylumbelliferyl xylosides and a structure–activity study of human β4GalT7 - Université de Lorraine Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2017

Synthesis of a library of variously modified 4-methylumbelliferyl xylosides and a structure–activity study of human β4GalT7

Abstract

Proteoglycans (PGs) are complex macromolecules that are composed of glycosaminoglycan (GAG) chains covalently attached to a core protein through a tetrasaccharide linker. The biosynthesis of PGs is complex and involves a large number of glycosyltranferases. Here we present a structure–activity study of human β4GalT7, which transfers the first Gal residue onto a xyloside moiety of the linkage region. An efficient and regiocontrolled synthesis of a library of modified analogs of 4-methylumbelliferyl xyloside (XylMU) is reported herein. Hydroxyl groups at the position C-2, C-3 or C-4 have been epimerized and/or replaced by a hydrogen or a fluorine, while the anomeric oxygen was replaced by either a sulfur or a sulfone. The effect of these compounds on human β4GalT7 activity in vitro and on GAG biosynthesis in cellulo was then evaluated.
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hal-01709254 , version 1 (14-02-2018)

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Samir Dahbi, Jean-Claude Jacquinet, Isabelle Bertin-Jung, Anne Robert, Nick Ramalanjaona, et al.. Synthesis of a library of variously modified 4-methylumbelliferyl xylosides and a structure–activity study of human β4GalT7. Organic & Biomolecular Chemistry, 2017, 15 (45), pp.9653 - 9669. ⟨10.1039/c7ob02530k⟩. ⟨hal-01709254⟩
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