Synthesis of all-cis 2,5-imino-2,5-dideoxy-fucitol and its evaluation as a potent fucosidase and galactosidase inhibitor.
Bioorg Med Chem Lett
; 20(24): 7410-3, 2010 Dec 15.
Article
em En
| MEDLINE
| ID: mdl-21050758
ABSTRACT
We here describe a simple and efficient synthetic method for a non-hydrolysable precursor of a GDP-fucose analogue The synthesis of the racemic aminofuranofucitol 3 from sorbic alcohol by nitroso-Diels-Alder reaction. This 'all-cis-pyrrolidine', with all substituents occupying a cis position, has been determined as a potent inhibitor of α-L-fucosidase and a moderate inhibitor of α- and ß-D-galactosidase. The good recognition of this fucose moiety analogue by specific enzymes is thus confirmed. The C-anomeric bond in this particular structure is in the ß-position and makes this compound an interesting candidate for further chemical modifications. Influence of the methyl and hydroxymethyl groups on the inhibition potency is discussed.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Pirrolidinas
/
Álcoois Açúcares
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1-Desoxinojirimicina
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Inibidores Enzimáticos
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Alfa-L-Fucosidase
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Galactosidases
Idioma:
En
Ano de publicação:
2010
Tipo de documento:
Article