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Issue 45, 2017
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Synthesis of a library of variously modified 4-methylumbelliferyl xylosides and a structure–activity study of human β4GalT7

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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.

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

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Publication details

The article was received on 12 Oct 2017, accepted on 27 Oct 2017 and first published on 27 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02530K
Citation: Org. Biomol. Chem., 2017,15, 9653-9669
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    Synthesis of a library of variously modified 4-methylumbelliferyl xylosides and a structure–activity study of human β4GalT7

    S. Dahbi, J. Jacquinet, I. Bertin-Jung, A. Robert, N. Ramalanjaona, S. Gulberti, S. Fournel-Gigleux and C. Lopin-Bon, Org. Biomol. Chem., 2017, 15, 9653
    DOI: 10.1039/C7OB02530K

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