Organic Letters 1999-09-09

Anomer-selective inhibition of glycosidases using aminocyclopentanols.

E Leroy, J L Reymond

Index: Org. Lett. 1(5) , 775-7, (1999)

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Abstract

[reaction: see text] (1S,2S,3S,4R,5R)-4-amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1 is prepared stereoselectively from D-lyxose and displays anomer-selective inhibition for beta-galactosidase (Ki = 3.0 x 10(-6) M) and beta-glucosidase (Ki = 1.5 x 10(-7) M), over alpha-galactosidase (Ki = 2.3 x 10(-5) M) and alpha-glucosidase (IC50 = 1.0 x 10(-4) M). There is no observable cross-reactivity with alpha-mannosidase, beta-mannosidase, or alpha-L-fucosidase.

Related Compounds

  • Cyclopentanol

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