Now, writing in Nature, Benjamin Davis, Ming Joo Koh and co-workers report a photoinduced method for chemical glycosylation, which can use unprotected native sugars. A ‘cap and glycosylate’ method is developed which converts the more acidic anomeric hydroxyl group of the native sugar or carbohydrate substrate to the corresponding 2,3,5,6-tetrafluoropyridine-4-thioglycoside (capping), and then uses a desulfurative coupling reaction to form a range of C-, S-, Se-, and O-glycosides (glycosylating).
“Glycosyltransferases can promote selective glycosylation at the anomeric site without protecting groups,” says Koh. “We wanted to mimic that by designing a chemical approach to directly activate and functionalize native sugars to access the desired glycoside products.”
“Glycosyltransferases can promote selective glycosylation at the anomeric site without protecting groups,” says Koh. “We wanted to mimic that by designing a chemical approach to directly activate and functionalize native sugars to access the desired glycoside products.”
Protecting-group-free radical glycosylation | Nature Synthesis
