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The synthesis of tetrazoles derived from D-manno and D- rhamnopyranose from L-gulonolactone and of L-rhamnopyranose from D-gulonolactone is described. These and other materials are assessed as inhibitors of glycosidases. The [4.3.0] tetrazoles of D-manno- and D-rhamnopyranose are inhibitors of human liver α-mannosidase. In contrast the D-furanose analogues show no inhibitory activity whilst the [3.3.0] L-rhamno furanotetrazole is a potent rhamnosidase inhibitor, a potential inhibitor of mycobacterial cell wall biosynthesis and as such may provide a strategy for the treatment of tuberculosis.

Original publication

DOI

10.1016/S0040-4020(99)00137-4

Type

Journal article

Journal

Tetrahedron

Publication Date

01/01/1999

Volume

55

Pages

4489 - 4500