Design and Synthesis of Aminocyclopentanol Glycosidase Inhibitors: Modification of Mannostatin A and Trehazolamine

Title: Design and Synthesis of Aminocyclopentanol Glycosidase Inhibitors: Modification of Mannostatin A and Trehazolamine

Volume: 6 Issue: 1

Author(s): Seiichiro Ogawa, Miki Kanto and Chikara Uchida

Affiliation:

Keywords: Drug design, glycosidase inhibitors, aminocyclitols, bioactive cyclitols, natural product syntheses, diastereoselective synthesis, chemical modification, structure-inhibitory activity relationships

Abstract: Convenient synthesis of the α-mannosidase inhibitor mannostatin A from myo-inositol is described by a method, which is generally applicable for provision of aminocyclopentanols of biological interest. Elucidation of structure-inhibitory activity relationships was carried out by chemical modification, leading to discovery of a very potent amino(methoxy)cyclopentanetriol. Similar studies of the trehalase inhibitor trehazolin stimulated development of a new type of aminocyclopentanol glycosidase inhibitor featuring ring contract mimicking of valiolamine, with implications for understanding of the structure and activity relationships of glycosidase inhibitors of this type.

Cite this article as:

Ogawa Seiichiro, Kanto Miki and Uchida Chikara, Design and Synthesis of Aminocyclopentanol Glycosidase Inhibitors: Modification of Mannostatin A and Trehazolamine, Current Bioactive Compounds 2010; 6 (1) . https://dx.doi.org/10.2174/157340710790711791