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Naphthyl Thio- and Carba-xylopyranosides for Exploration of the Active Site of-1,4-Galactosyltransferase 7 (4GalT7)
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-5657-8635
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2017 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 71, p. 18057-18065Article in journal (Refereed) Published
Abstract [en]

Xyloside analogues with substitution of the endocyclic oxygen atom by sulfur or carbon were investigated as substrates for -1,4-galactosyltransferase7 (4GalT7), a key enzyme in the biosynthesis of glycosaminoglycan chains. The analogues with an endocyclic sulfur atom proved to be excellent substrates for 4GalT7, and were galactosylated approximately fifteen times more efficiently than the corresponding xyloside. The 5a-carba--xylopyranoside in the d-configuration proved to be a good substrate for 4GalT7, whereas the enantiomer in the l-configuration showed no activity. Further investigations by X-ray crystallography, NMR spectroscopy, and molecular modeling provided a rationale for the pronounced activity of the sulfur analogues. Favorable - interactions between the 2-naphthyl moiety and a tyrosine side chain of the enzyme were observed for the thio analogues, which open up for the design of efficient GAG primers and inhibitors.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2017. Vol. 23, no 71, p. 18057-18065
Keywords [en]
carbohydrates, enzymes, structure-activity relationships, xylosides
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-152501DOI: 10.1002/chem.201704267ISI: 000418356700030PubMedID: 29024190OAI: oai:DiVA.org:su-152501DiVA, id: diva2:1181057
Funder
Magnus Bergvall FoundationSwedish Research CouncilKnut and Alice Wallenberg Foundation
Note

Open Access 2020-01-01

Available from: 2018-02-07 Created: 2018-02-07 Last updated: 2019-09-06Bibliographically approved

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