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

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Abstract

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.

Details

Authors
Organisations
External organisations
  • Lund University
Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Organic Chemistry
Original languageEnglish
Pages (from-to)1259-1277
Number of pages19
JournalJournal of Organic Chemistry
Volume83
Issue number3
Publication statusPublished - 2018 Feb 2
Publication categoryResearch
Peer-reviewedYes