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Cyclic amidine sugars as transition-state analogue inhibitors of glycosidases: Potent competitive inhibitors of mannosidases

Academic Article
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Overview

authors

  • Heck, M. P.
  • Vincent, S. P.
  • Murray, B. W.
  • Bellamy, F.
  • Wong, Chi-Huey
  • Mioskowski, C.

publication date

  • February 2004

journal

  • Journal of the American Chemical Society  Journal

abstract

  • A series of monocyclic glycoamidines bearing different exocyclic amine, alcohol, or alkyl functionalities and bicyclic amidines derived from D-glucose and D-mannose were synthesized and tested as inhibitors of various glycosidases. All the prepared compounds demonstrated good to excellent inhibition toward glycosidases. In particular, the biscationic D-mannoamidine 9b bearing an exocyclic ethylamine moiety proved to be a selective competitive inhibitor of alpha- and beta-mannosidases (K(i) = 6 nM) making it the most potent inhibitor of these glycosidases reported to date. A favorable B(2,5) boat conformation might explain the selectivity of mannosidase inhibition compared to other glycosidases.

subject areas

  • Amidines
  • Binding, Competitive
  • Carbohydrate Conformation
  • Carbohydrate Metabolism
  • Carbohydrates
  • Enzyme Inhibitors
  • Mannosidases
  • Structure-Activity Relationship
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja037822r

PubMed ID

  • 14971930
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Additional Document Info

start page

  • 1971

end page

  • 1979

volume

  • 126

issue

  • 7

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