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Review | Special issue | Vol 67, No. 1, 2006, pp.461-488
Published online, 26th August, 2005
DOI: 10.3987/REV-05-SR(T)3
gem-Diamine 1-N-Iminosugars, a New Family of Glycosidase Inhibitors: Synthesis and Biological Activity

Yoshio Nishimura

*Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan

Abstract

Specific inhibitors of glycosidases are useful for unraveling how glycoconjugates regulate biological functions, and also for developing the new drugs for the serious diseases associated with both the biosynthesis and the degradation of glycoconjugate such as cancer, tumor metastasis, inflammatory disorders, viral and bacterial infections and so forth. This article describes the synthesis and biological activity of gem-diamine 1-N-iminosugars, a new class of glycosidase inhibitors, with a nitrogen atom in place of the anomeric carbon. New inhibitors that may mimic the glycopyranosyl cation, the putative intermediate of enzymatic glycosidic hydrolysis, have shown strong and specific inhibition against glycosidases. The inhibitors also illustrate a promising candidate of new drugs for tumor metastasis.