Synthesis of Double-Modified Xyloside Analogues for Probing the β4GalT7 Active Site
Research output: Contribution to journal › Article
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.
|Research areas and keywords||
Subject classification (UKÄ) – MANDATORY
|Number of pages||19|
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 2018 Feb 2|