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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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https://hal.univ-lorraine.fr/hal-01709254
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Submitted on : Wednesday, February 14, 2018 - 5:14:48 PM
Last modification on : Wednesday, November 3, 2021 - 7:55:59 AM

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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 and Biomolecular Chemistry, Royal Society of Chemistry, 2017, 15 (45), pp.9653 - 9669. ⟨10.1039/c7ob02530k⟩. ⟨hal-01709254⟩

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