title: Picomole scale stereochemical analysis of sphingosines and dihydrosphingosines.
abstract: We have developed a simple picomole (low nanogram) scale HPLC scheme which can separate all eight isomers of sphingosine and dihydrosphingosine thus leading to the identification of their relative and absolute configurations. The amino group of the sample is derivatized to its fluorescent N-naphthimide which is analyzed by normal and chiral phase HPLC, coupled with fluorescence peak detection. If necessary, the results of this HPLC method can be further corroborated by measurements of circular dichroic (CD) spectra of the N-naphthimido-derivatives and/or N,O-chromophoric derivatives.
authors.affiliation: Department of Chemistry, Columbia University, New York, NY 10027, USA.
authors.forename: A
authors.initials: A
authors.lastname: Kawamura
authors.forename: N
authors.initials: N
authors.lastname: Berova
authors.forename: V
authors.initials: V
authors.lastname: Dirsch
authors.forename: A
authors.initials: A
authors.lastname: Mangoni
authors.forename: K
authors.initials: K
authors.lastname: Nakanishi
authors.forename: G
authors.initials: G
authors.lastname: Schwartz
authors.forename: A
authors.initials: A
authors.lastname: Bielawska
authors.forename: Y
authors.initials: Y
authors.lastname: Hannun
authors.forename: I
authors.initials: I
authors.lastname: Kitagawa
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D004791:Enzyme Inhibitors / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011493:Protein Kinase C / Q000037:antagonists & inhibitors*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004791:Enzyme Inhibitors; D011493:Protein Kinase C; D013110:Sphingosine; C005682:safingol