The browser you are using is not supported by this website. All versions of Internet Explorer are no longer supported, either by us or Microsoft (read more here: https://www.microsoft.com/en-us/microsoft-365/windows/end-of-ie-support).

Please use a modern browser to fully experience our website, such as the newest versions of Edge, Chrome, Firefox or Safari etc.

Default user image.

Sophie Manner

Director of studies

Default user image.

Synthesis of Double-Modified Xyloside Analogues for Probing the β4GalT7 Active Site

Author

  • Daniel Willén
  • Dennis Bengtsson
  • Sebastian Clementson
  • Emil Tykesson
  • Sophie Manner
  • Ulf Ellervik

Summary, in English

Monosubstituted naphthoxylosides have been shown to function as substrates for, and inhibitors of, the enzyme β4GalT7, a key enzyme in the biosynthetic pathway leading to glycosaminoglycans and proteoglycans. In this article, we explore the synthesis of 16 xyloside analogues, modified at two different positions, as well as their function as inhibitors of and/or substrates for the enzyme. Seemingly simple compounds turned out to require complex synthetic pathways. A meta-analysis of the synthetic work shows that, regardless of the abundance of methods available for carbohydrate synthesis, even simple modifications can turn out to be problematic, and double modifications present additional challenges due to conformational, steric, and stereoelectronic effects.

Department/s

  • Centre for Analysis and Synthesis

Publishing year

2018-02-02

Language

English

Pages

1259-1277

Publication/Series

Journal of Organic Chemistry

Volume

83

Issue

3

Document type

Journal article

Publisher

The American Chemical Society (ACS)

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 0022-3263