Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
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.
Show others and affiliations
Number of Authors: 102017 (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
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
Available from: 2018-02-07 Created: 2018-02-07 Last updated: 2018-02-07Bibliographically approved

Open Access in DiVA

No full text in DiVA

Other links

Publisher's full textPubMed

Search in DiVA

By author/editor
Ståhle, JonasWidmalm, GöranEllervik, Ulf
By organisation
Department of Organic Chemistry
In the same journal
Chemistry - A European Journal
Chemical Sciences

Search outside of DiVA

GoogleGoogle Scholar

doi
pubmed
urn-nbn

Altmetric score

doi
pubmed
urn-nbn
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf