Preparation and analysis of benzoylated cerebrosides.
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.
D000478:Alkylation; D001565:Benzoates / Q000032:analysis; D002554:Cerebrosides / Q000032:analysis* / Q000138:chemical synthesis; D002725:Chloroform; D002845:Chromatography; D004121:Dimethyl Sulfoxide; D005227:Fatty Acids; D005690:Galactose / Q000032:analysis; D006027:Glycosides / Q000032:analysis; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D011725:Pyridines; D012972:Sodium Hydroxide; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013110:Sphingosine / Q000032:analysis
D001565:Benzoates; D002554:Cerebrosides; D005227:Fatty Acids; D006027:Glycosides; D011725:Pyridines; D012972:Sodium Hydroxide; D002725:Chloroform; D013110:Sphingosine; D005690:Galactose; D004121:Dimethyl Sulfoxide