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Journal of Lipid Research, Vol. 14, 611-617, November 1973
Copyright © 1973 by Lipid Research, Inc.

Preparation and analysis of benzoylated cerebrosides

Robert H. McCluer and James E. Evans

Eunice Kennedy Shriver Center for Mental Retardation, W. E. Fernald State School, Waltham, Massachusetts 02154 and Department of Biochemistry, Boston University, Boston, Massachusetts 02118

The benzoylation of cerebrosides with benzoyl chloride and with benzoic anhydride is described, and the derivatives that contained hydroxy and nonhydroxy fatty acids were isolated by high pressure liquid chromatography (HPLC). Studies on the structures of these derivatives and the products formed by mild alkaline hydrolysis are reported. Reaction of cerebrosides containing nonhydroxy fatty acids with benzoyl chloride results in amide-acylation in addition to normal O-acylation. Mild alkali treatment of the N-diacyl derivative results in the formation of N-benzoyl psychosine. Derivatization with benzoic anhydride avoids amide-acylation. These derivatives are useful for the HPLC analysis of cerebrosides.

Supplementary key words high pressure liquid chromatography benzoyl chloride • benzoic anhydride • nuclear magnetic resonance

Submitted on December 14, 1972
Revised on June 15, 1973
Accepted on July 10, 1973


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