TY - JOUR
T1 - From glycoside hydrolases to thioglycoligases: the synthesis of thioglycosides
AU - Stick, Robert
AU - Stubbs, Keith
PY - 2005
Y1 - 2005
N2 - 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. (C) 2004 Elsevier Ltd. All rights reserved.
AB - 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. (C) 2004 Elsevier Ltd. All rights reserved.
U2 - 10.1016/j.tetasy.2004.12.004
DO - 10.1016/j.tetasy.2004.12.004
M3 - Article
SN - 0957-4166
VL - 16
SP - 321
EP - 335
JO - Tetrahedron: Asymmetry
JF - Tetrahedron: Asymmetry
IS - 2
ER -