141020-13-5Relevant articles and documents
From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides
Stick, Robert V.,Stubbs, Keith A.
, p. 321 - 335 (2007/10/03)
The treatment of various glycosyl acceptors, each containing a reactive thiol group, with the appropriate glycosyl donor and a glycoside hydrolase or glycosynthase, failed to yield any thioglycosides - only the products of O-glycosylation were formed. However, thioglycosides were formed when a thioglycoligase was used to mediate the reaction between acceptor and donor. In fact, pyranose acceptors possessing a thiol group at C3, C4 or C6 (but not C2) were all capable of conversion into thioglycosides. Some comment is given regarding the mechanism of the various processes.