Glycosidase Inhibition by All 10 Stereoisomeric 2,5-Dideoxy-2,5-iminohexitols Prepared from the Enantiomers of Glucuronolactone

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• 作者：Benjamin J. Ayers ; Nigel Ngo ; Sarah F. Jenkinson ; R. Fernando Mart铆nez ; Yousuke Shimada ; Isao Adachi ; Alexander C. Weymouth-Wilson ; Atsushi Kato ; George W. J. Fleet
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：September 21, 2012
• 年：2012
• 卷：77
• 期：18
• 页码：7777-7792
• 全文大小：690K
• 年卷期：v.77,no.18(September 21, 2012)
• ISSN：1520-6904

文摘

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.