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Exploring a multivalent approach to α-L-fucosidase inhibition

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Published copy (DOI)

Author(s)

  • Elena Moreno-Clavijo
  • Ana T. Carmona
  • Antonio J. Moreno-Vargas
  • Lidia Molina
  • Daniel W. Wright
  • Gideon J. Davies
  • Inmaculada Robina

Department/unit(s)

Publication details

JournalEuropean Journal of Organic Chemistry
DateE-pub ahead of print - 19 Sep 2013
DatePublished (current) - 10 Oct 2013
Issue number32
Number of pages9
Pages (from-to)7328-7336
Early online date19/09/13
Original languageEnglish

Abstract

To probe the utility of a multivalent approach for fucosidase inhibition, a series of di- and tri-valent imino sugars based on L-fuco-configured 1,4-imino- and 1,4-bis(imino)-cyclitol epitopes has been synthesized and analyzed for fucosidase inhibition with the best trivalent species yielding a modest improvement in binding constant. Structural analysis of a representative pair of mono- and tri-valent imino sugars has been performed on a bacterial fucosidase, BtFuc2970. The 3D structures show binding of the imino-cyclitol in the 3E conformation, consistent with the known pathway for fucosidase action. Di- and tri-valent imino sugars based on L-fuco-configured 1,4-imino- and 1,4-bis(imino)-cyclitol moieties present α-L-fucosidase inhibitory activities in the μM and nM range.

    Research areas

  • Carbohydrates, Enzymes, Glycoconjugates, Imino sugars, Inhibitors, Structure-activity relationships

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