Chemistry of Succinimido Esters. XVII.*1

The erythro/threo Separation of Sphingolipid Bases Labelled with N-Succinimidyl Benzoates by Normal Phase HPLC

Abstract

The sensitive determination of erythro/threo ratios of sphingolipid bases without trimethylsilylation was made using synthetic Cn-dihydrosphingosines (1) labelled by N-succinimidyl benzoates (2). Compound (1) reacted with (2) in a refluxing acetonitrile to give the corresponding N-arylcarbonyl derivative, (3). The erythro and threo isomers of (1) could be separated on a normal phase HPLC column in the form of (3) which was detectable at 254nm. The erythro content of (1) as determined by the present method using (2) with a different substituent showed good agreement and was essentially the same as that by the GLC method using O, O-di-TMS derivative of (3).