Stereoselective synthesis of (2S,3S,4R,5S)-5-methylpyrrolidine-3,4-diol derivatives that are highly selective alpha-L-fucosidase inhibitors

Antonio J Moreno-Vargas; Ana T Carmona; Federico Mora; Pierre Vogel; Inmaculada Robina

doi:10.1039/b508855k

Stereoselective synthesis of (2S,3S,4R,5S)-5-methylpyrrolidine-3,4-diol derivatives that are highly selective alpha-L-fucosidase inhibitors

Chem Commun (Camb). 2005 Oct 21:(39):4949-51. doi: 10.1039/b508855k. Epub 2005 Sep 8.

Authors

Antonio J Moreno-Vargas¹, Ana T Carmona, Federico Mora, Pierre Vogel, Inmaculada Robina

Affiliation

¹ Department of Organic Chemistry, Faculty of Chemistry, University of Seville, P. O. Box 553, E-41071 Seville, Spain.

PMID: 16205810
DOI: 10.1039/b508855k

Abstract

N-Phenylaminomethyl benzimidazolyl moieties attached at C-2 of (2S,3S,4R,5S)-5-methylpyrrolidine-3,4-diol increase the potency and selectivity of the inhibitory activity of these systems towards alpha-L-fucosidases.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology*
Molecular Structure
Pyrrolidines / analysis*
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry
Stereoisomerism
alpha-L-Fucosidase / antagonists & inhibitors*
alpha-L-Fucosidase / metabolism

Substances

(2S,3S,4R,5S)-5-methylpyrrolidine-3,4-diol
Enzyme Inhibitors
Pyrrolidines
alpha-L-Fucosidase