[Application of glycosyl fluorides in the study on glycosidases].
Glycosyl fluorides are becoming increasingly important molecules for the study on glycosidases. Firstly, glycosyl fluorides act as substrates for glycosidases hydrolysis. Scecondly, the installation of fluorine elsewhere on the carbohydrate ring modifies the properties of the glycosyl fluoride so that the resultant compounds act as mechanism-based inhibitors to label enzymes in the active site, allowing identification of the catalytic nucleophile. Furthermore, glycosyl fluorides also act as donors for transglycosylation by retaining glycolides. Finally, glycosyl fluorides of the wrong anomeric configuration could be used by retaining glycosidase mutants such as glycosynthases and thioglycosynthases to synthesize carbohydrate with high yields(normally 60% to approximately 90%). Fundamental and applied research in biology, glycobiology and nanobiotechnology would benefit from the possibility of synthesizing tailor-made oligo-/poly-saccharides.
Lu
Li-Li
LL
State Key Laboratory of Microbial Technology, Shandong University, Shandong 250100, China.
Xiao
Min
M
Zhao
Han
H
Wang
Peng
P
Qian
Xin-Min
XM
D000818:Animals; D004791:Enzyme Inhibitors / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry*; D005959:Glucosidases / Q000378:metabolism*; D006026:Glycoside Hydrolases / Q000378:metabolism*; D006027:Glycosides / Q000737:chemistry*; D016695:Glycosyltransferases / Q000378:metabolism; D006801:Humans; D006868:Hydrolysis; D013379:Substrate Specificity
D004791:Enzyme Inhibitors; D006027:Glycosides; D016695:Glycosyltransferases; D005959:Glucosidases; D006026:Glycoside Hydrolases; D005459:Fluorides