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Journal of Lipid Research, Vol. 41, 2089-2093, December 2000
Copyright © 2000 by Lipid Research, Inc.

Methods

Methanolysis of sphingomyelin: toward an epimerization-free methodology for the preparation of D-erythro-sphingosylphosphocholine

Correspondence to: Robert Bittman

It is well known that acid hydrolysis of natural sphingomyelin in aqueous methanol or 1-butanol at refluxing temperature is accompanied by epimerization at the C-3 position of the long-chain base. An improved procedure for the hydrolysis of commercially available, naturally occurring sphingomyelin is described. Prolonged exposure (3;–4 days) of sphingomyelin to freshly prepared 0.5 M anhydrous methanolic hydrogen chloride (generated by trapping the gas evolved from the reaction of concentrated sulfuric acid with solid sodium chloride in anhydrous methanol) at 50°C resulted in cleavage of the amide side chain. The extent of epimerization of the allylic alcohol stereocenter was quantified by integration of the C-5 signal of the ¹³C nuclear magnetic resonance spectrum of lysosphingomyelin.

The method described here is superior to the traditional acid hydrolysis methods because it provides the product as a 10:1 ratio of D-erythro/L-threo epimers; in contrast, a ratio of 1.3:1 was obtained by the previous methods. We also report that use of dichloromethane as a cosolvent with N,N-dimethylformamide in the reaction of lysosphingomyelin with an activated fatty acid reduced the time required for completion of the N-acylation reaction. — Bittman, R., and C. A. Verbicky. Methanolysis of sphingomyelin: toward an epimerization-free methodology for the preparation of D-erythro-sphingosylphosphocholine. J. Lipid Res. 2000. 41: 2089;–2093.

Supplementary key words: lysosphingomyelin, acid hydrolysis, acylation of lysosphingomyelin

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