Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 3, 2013
Previous Article Next Article

On the reactivity and selectivity of donor glycosides in glycochemistry and glycobiology: trapped covalent intermediates

Author affiliations

Abstract

The reactivity of sugar donors and the stability of covalent intermediates formed in both chemical and biological systems is an active subject of study in both glycochemistry and glycobiology. Knowledge of the structure of these intermediates is vital for understanding reactivity and stereoselectivity in glycosidic bond formation, and in glycosidic bond destruction in the case of enzymatic hydrolysis. For chemical reactions, tuning of the electron-withdrawing power of the carbohydrate side chains allows for stabilization of covalent anomeric triflates thereby enabling chemo-, regio- and stereoselective glycosylations. Retaining glycosidase-mediated hydrolysis reactions in turn often involve a covalent intermediate. The existence of such covalent intermediates was convincingly demonstrated at the beginning of this century by making use of modified glycosyl substrates tuned such that stable adducts are formed efficiently but the ensuing hydrolysis is slowed down. Recently this concept has also been used in the design of glycosidase activity-based probes. This review describes recent investigations on different carbohydrate decoration patterns to influence both chemical and biological reactivity and selectivity.

Graphical abstract: On the reactivity and selectivity of donor glycosides in glycochemistry and glycobiology: trapped covalent intermediates

Back to tab navigation

Article information


Submitted
27 Sep 2012
Accepted
05 Nov 2012
First published
06 Nov 2012

Chem. Sci., 2013,4, 897-906
Article type
Perspective

On the reactivity and selectivity of donor glycosides in glycochemistry and glycobiology: trapped covalent intermediates

M. T. C. Walvoort, G. A. van der Marel, H. S. Overkleeft and J. D. C. Codée, Chem. Sci., 2013, 4, 897
DOI: 10.1039/C2SC21610H

Social activity

Search articles by author

Spotlight

Advertisements