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Aglycon specificity profiling of alpha-glucosidases using synthetic probes.

Hakamata W, Muroi M, Kadokura K, Nishio T, Oku T, Kimura A, Chiba S, Takatsuki A

Animal and Cellular Systems Laboratory, The Institute of Physical and Chemical Research (RIKEN), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan. hakamata@nihs.go.jp

We designed and synthesized hydrogen bond based probes 1-8 with the exception of known glycosidase inhibition mechanisms, and aglycon specificity of 11 different sources of alpha-glucosidases were investigated using their probes. Probe 4 (2,6-anhydro-1-deoxy-1-[(1-oxopentyl-5-hydroxy)amino]-D-glycero-D-ido-heptitol) showed a potent inhibition of S. cerevisiae alpha-glucosidase among all alpha-glucosidases. Probe 4 was found to be a competitive inhibitor for S. cerevisiae alpha-glucosidase with Ki 0.13 mM.

Published 16 February 2005 in Bioorg Med Chem Lett, 15(5): 1489-92.
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