From glycoside hydrolases to thioglycoligases: the synthesis of thioglycosides |
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| Institution: | 1. Department of Mathematics and Natural Sciences, College of Sciences and Human Studies, Prince Mohammad Bin Fahd University, Al Khobar, Kingdom of Saudi Arabia;2. Department of Mathematics and Natural Sciences, College of Sciences and Human Studies, Deanship of Research Development, Prince Mohammad Bin Fahd University, Al Khobar, Kingdom of Saudi Arabia;1. Department of Pharmaceutical Chemistry, University of Debrecen, Debrecen, Hungary;2. Research Group for Oligosaccharide Chemistry of HAS, University of Debrecen, Debrecen, Hungary;3. Glycoptim Ltd., Debrecen, Hungary |
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| Abstract: | 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. |
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