Structural and biochemical evidence for a boat-like transition state in β-mannosidases View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2008-05

AUTHORS

Louise E Tailford, Wendy A Offen, Nicola L Smith, Claire Dumon, Carl Morland, Julie Gratien, Marie-Pierre Heck, Robert V Stick, Yves Blériot, Andrea Vasella, Harry J Gilbert, Gideon J Davies

ABSTRACT

Enzyme inhibition through mimicry of the transition state is a major area for the design of new therapeutic agents. Emerging evidence suggests that many retaining glycosidases that are active on alpha- or beta-mannosides harness unusual B2,5 (boat) transition states. Here we present the analysis of 25 putative beta-mannosidase inhibitors, whose Ki values range from nanomolar to millimolar, on the Bacteroides thetaiotaomicron beta-mannosidase BtMan2A. B2,5 or closely related conformations were observed for all tightly binding compounds. Subsequent linear free energy relationships that correlate log Ki with log Km/kcat for a series of active center variants highlight aryl-substituted mannoimidazoles as powerful transition state mimics in which the binding energy of the aryl group enhances both binding and the degree of transition state mimicry. Support for a B2,5 transition state during enzymatic beta-mannosidase hydrolysis should also facilitate the design and exploitation of transition state mimics for the inhibition of retaining alpha-mannosidases--an area that is emerging for anticancer therapeutics. More... »

PAGES

306

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/nchembio.81

DOI

http://dx.doi.org/10.1038/nchembio.81

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1044600073

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/18408714


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