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

Journal article

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.

Authors: Ayers, B; Ngo, N; Jenkinson, S; Martínez, R; Shimada, Y

• Publication status: Published
• Journal: Journal of organic chemistry More from this journal
• Volume: 77
• Issue: 18
• Pages: 7777-7792
• Publication date: 2012-09-01
• DOI: 10.1021/jo301243s
• EISSN: 1520-6904
• ISSN: 0022-3263
• Language: English
• Keywords: Glucuronates; Stereoisomerism; Enzyme Inhibitors; Imino Sugars; Glycoside Hydrolases; Structure-Activity Relationship