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Naphthyl Thio- and Carba-xylopyranosides for Exploration of the Active Site of-1,4-Galactosyltransferase 7 (4GalT7)
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0001-5657-8635
Vise andre og tillknytning
2017 (engelsk)Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, nr 71, s. 18057-18065Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
Wiley-VCH Verlagsgesellschaft, 2017. Vol. 23, nr 71, s. 18057-18065
Emneord [en]
carbohydrates, enzymes, structure-activity relationships, xylosides
HSV kategori
Identifikatorer
URN: urn:nbn:se:su:diva-152501DOI: 10.1002/chem.201704267ISI: 000418356700030PubMedID: 29024190OAI: oai:DiVA.org:su-152501DiVA, id: diva2:1181057
Forskningsfinansiär
Magnus Bergvall FoundationSwedish Research CouncilKnut and Alice Wallenberg Foundation
Merknad

Open Access 2020-01-01

Tilgjengelig fra: 2018-02-07 Laget: 2018-02-07 Sist oppdatert: 2019-09-06bibliografisk kontrollert

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