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2005
Carbohydrates
U 0500
Looking Glass Inhibitors: L-DMDP, a More Potent and Specific Inhibitor
of α-Glucosidases than the Enantiomeric Natural Product DMDP. —
05- 185 L-DMDP
(VII), a pyrrolidine-based sugar mimic, is synthesized from the acetonide (I)
of D-gulonolactone in an overall yield of approximately 11%. The formation of (VII)
requires the introduction of a nitrogen bridge between C-2, with retention of configuration, and C-5, with inversion of configuration, and adjustment of the oxidation level
at C-1. An azide epimerization is necessary to equilibrate the trans-azido-lactone (II)
to the more stable all cis-azido-lactone (III). The correct oxidation level at C-1 is
achieved by reduction of (III). Finally, a leaving group at C-5 is installed, prior to reduction of the azide to permit cyclization by the amine. L-DMDP is a highly specific
inhibitor of a number of plant and mammalian α-glucosidases but is not an inhibitor of
bacterial and yeast α-glucosidases. — (YU, C.-Y.; ASANO, N.; IKEDA, K.; WANG,
M.-X.; BUTTERS, T. D.; WORMALD, M. R.; DWEK, R. A.; WINTERS, A. L.;
NASH, R. J.; FLEET*, G. W. J.; Chem. Commun. (Cambridge) 2004, 17, 1936-1937;
Chem. Res. Lab., Dep. Chem., Univ. Oxford, Oxford OX1 3TA, UK; Eng.) —
H. Hoennerscheid
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