Electron impact and chemical ionization mass spectrometry of cyclic boronate derivatives of sphingosines and related compounds

0030-493X

Chemistry ; Analytical Chemistry and Spectroscopy

Wiley InterScience Backfile Collection 1832-2000

Chemistry and Pharmacology

Electron impact and isobutane chemical ionization mass spectrometric data are reported for cyclic boronate esters of sphinganine and 4-sphingenine and of the related N-ethyl, N-dimethylaminomethylene and acetone Schiff base compounds. Fragmentation of the 6-membered boronate ring is promoted by the presence of the 2-amino or 2-imino substituent and by Δ4 unsaturation. Evidence is presented for a transannular interaction stabilizing the ion formed by loss of the alkyl or aryl group, attached to the boron atom, in the case of the N-dimethylaminomethylene derivatives. An NH2 migration is postulated to occur in 4-sphingenine boronates under electron impact. Mass spectrometric data are also reported for 4D-hydroxysphinganine bis-boronates.

2 Ill.

Electronic Resource