Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 7, Issue 6, Pages 1192-1202Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b819867e
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Funding
- Ministerio de Educacion y Ciencia of Spain [CTQ2004-00649/BQU, CTQ2007-61254/BQU, CTQ2008-01565/BQU]
- Junta de Andalucia [FQM-345]
- Swiss National Science Foundation
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The stereoselective synthesis of new 3,4-dihydroxypyrrolidine derivatives starting from D-mannose, D-ribose and L-fucose is presented. Two synthetic strategies employing organometallic addition to hemiacetalic sugars followed by selective nucleophilic displacement or conjugate addition of ammonia to conjugate aldonic esters as key steps, are used. The new compounds were assayed for their inhibitory activity towards 13 commercially available glycosidases. Compounds that share the absolute configuration at C(2,3,4,5) of L-fucopyranosides and incorporate aromatic moieties are potent and selective inhibitors of alpha-L-fucosidases in the nM range.
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