Direct Radical Functionalization of Native Sugars
Benjamin Davis and Ming Joo Koh use a ‘cap and glycosylate’ strategy to radically functionalize native sugars.
Carbohydrates exist ubiquitously in numerous living organisms, and their conjugates mediate various crucial biological processes. Inspired by biological S-glycosylation, a biomimetic ‘cap and glycosylate’ strategy to directly transfer native sugars into various classes of glycosides and glycoconjugates, thereby by-passing unnecessary protecting group manipulation, has been recently revealed by Professor Benjamin G. Davis from the Rosalind Franklin Institute and University of Oxford (both in the UK) and Prof. Ming Joo Koh (National University of Singapore, Singapore). This direct radical functionalization approach now provides a streamlined access to what the authors consider is essentially equivalent to a ‘clean’, unprotected glycosyl moiety that allows diverse and robust formation of C-, S-, Se-glycosides, as well as O-glycosides. Moreover, because of its aqueous and biocompatibility, this protocol can be readily and seamlessly applied even to biomacromolecules, realizing the direct post-translational chemical glycosylation of proteins from sugars that come directly from nature.
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