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Journal of Lipid Research, Vol. 14, 133-137, March 1973
Copyright © 1973 by Lipid Research, Inc.

N-Hexyl-O-glucosyl sphingosine, an inhibitor of glucosyl ceramide ßbeta;-glucosidase

John S. Erickson and Norman S. Radin

Mental Health Research Institute, University of Michigan, Ann Arbor, Michigan 48104

A synthetic analog of glucocerebroside, N-hexyl-O-glucosyl sphingosine, was found to inhibit the glucosidase in rat spleen that hydrolyzes glucocerebroside. At a concentration of 1 µm, the analog inhibited the enzyme by 48%. The mode of action appeared to be competitive, probably aided by tight binding of the amine group to a carboxyl group near the enzyme's active site. Increasing or decreasing the chain length of the n-alkyl group attached to the nitrogen atom led to decreased effectiveness. The inhibitory effect was maximal at pH 7.0, but it was still considerable at the enzyme's optimal pH, 5.0. It is suggested that the compound may be useful for inducing an animal model of Gaucher's disease.

Supplementary key words cerebroside glucosidase • glucosyl sphingosine preparation • cerebroside synthesis

Submitted on June 19, 1972
Accepted on October 24, 1972

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