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- W2132940503 abstract "Hammarstrom (6) has described a method to prepare ceramides by direct coupling of the long-chain bases and fatty acids in the presence of a mixed carbodiimide. No 0-acyl derivatives are formed. Yields of ceramide were 60-75% based on long-chain base and 30-37.5% based on fatty acid. N-Hydroxysuccinimide esters of fatty acids are stable crystalline compounds which are easily prepared in high yield (7). They have been used for the synthesis of N-acyl amino acids (7) and fatty acyl co~ (8). A~ described in this report, they can also be used for the direct Nacylation of sphingenine or sphinganine. The reaction proceeds in high yield from small amounts of starting material. The product ceramides are pure after one recrystallization. Materials. trans-2-Hexadecenoic acid was synthesized by the method of Shapiro, Segal, and Flowers (9). CERAMIDES have been implicated as intermediates in the Palmitic, stearic, and lignoceric acids were purchased biosynthesis of sphingomyelin and cerebrosides and are from Sigma Ckmical CO., St. Louis, Mo. [1-'4c1important constituents of all sphingolipids. '4C-labeled Palmitic and [ 1 -'4C]stearic acids were purchased from ceramides are useful as substrates for enzyme studies and New England Nuclear, Boston, Mass. N-Hydroxystudies of sphingolipid metabolism in the whole animal. succinimide (Aldrich Chemical CO., Milwaukee, Wis.) Some previously reported syntheses of ceramides was recrystallized from ethyl acetate before use. Dihave used appropriate fatty acid chlorides to acylate cyclohexylcarbodiimide was obtained from Pierce Chembenzoyl sphingenine or psychosine (1, 2). The inter- ical C0.j Rockford, 111. DL-Sphinganine (DL-erJ'thrO-173mediate compounds formed are then hydrolyzed to dihydroxy-2-aminooctadecane) was from Nutritional Bioproduce the desired ceramide. Direct acylation of chemical Corp., Cleveland, Ohio. DL-Sphingenine (DLsphingenine or sphinganine by an acid chloride can er~thro-trans-l,3-dih~drox~-2-amino-4-octadecene)" @default.
- W2132940503 created "2016-06-24" @default.
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- W2132940503 date "1972-11-01" @default.
- W2132940503 modified "2023-09-24" @default.
- W2132940503 title "Synthesis of ceramides using N-hydroxysuccinimide esters" @default.
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- W2132940503 doi "https://doi.org/10.1016/s0022-2275(20)39355-x" @default.
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