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Paper | Regular issue | Vol 100, No. 4, 2020, pp.609-621
Published online, 19th March, 2020
DOI: 10.3987/COM-20-14236
■ The Synthesis and Glycosidase Inhibitory Activity of Analogues of Tiruchanduramine

Zackary J. R. Ashworth, Barbara Bartholomew, Daniel M. Evans, Josephine Forde-Thomas, Karl F. Hoffmann, Reece Murdoch, Robert J. Nash, Hazel Sharp, Helen Whiteland, and Patrick J. Murphy*

*School of Natural Sciences, Bangor University, Gwynedd, LL57 2UW, UK

Abstract

Five analogues (7a-e) of the metabolite tiruchanduramine 1 were prepared. Compounds 7d and 7e were specific inhibitors of yeast α-glucosidase, whilst 7e specifically inhibited Bacillus α-glucosidase. Compounds 7b and 7c were the best inhibitors of β-glucosidase. All 5 compounds inhibited β-galactosidase, but once again 7e was the best inhibitor. It was apparent that different chain lengths in the compounds 7a-e affect the degree of inhibition. Some of the synthetic analogues show significantly improved inhibition of α-glucosidases when compared to tiruchanduramine 1 and also improved specificity.