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  • Glycosidase inhibition by all 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols prepared from the enantiomers of glucuronolactone.

Glycosidase inhibition by all 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols prepared from the enantiomers of glucuronolactone.

The Journal of organic chemistry (2012-08-30)
Benjamin J Ayers, Nigel Ngo, Sarah F Jenkinson, R Fernando Martínez, Yousuke Shimada, Isao Adachi, Alexander C Weymouth-Wilson, Atsushi Kato, George W J Fleet
ABSTRACT

The enantiomers of glucuronolactone are excellent chirons for the synthesis of the 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidine ring by nitrogen substitution at C2 and C5, with either retention or inversion of configuration; the stereochemistry at C3 may be adjusted during the synthesis to give seven stereoisomers from each enantiomer. A definitive side-by-side comparison of the glycosidase inhibition of a panel of 13 glycosidases showed that 8 of the 10 stereoisomers showed significant inhibition of at least one glycosidase.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
D-(+)-Glucuronic acid γ-lactone, ≥99%