Utility of Nicotinoyl Derivatives in Structural Studies of Mono- and Diacylglycerols by Gas Chromatography/Mass Spectrometry. Part 3—Application to Acylglycerols with Methyl Branchings and Epoxy and Cyclopropyl Rings

✍ Scribed by Zöllner, P.; Schmid, R.

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 597 KB
• Volume: 31
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/(sici)1096-9888(199604)31:4<411::aid-jms314>3.0.co;2-2

✦ Synopsis

Mono-and diacylglycerols with methyl branches and epoxy and cyclopropyl rings were synthesized and, suhsequently converted into their nicotinoyl derivatives by reaction with nicotinic acid and N,N'dicyclohexylcarhodiimide in the presence of N,N-dimethyl-4-aminopyridine. The resulting nicotinoyl derivatives were examined by gas chromatography/mass spectrometry (GC/MS). Their electron impact mass spectra reveal the structures of mono-and diacylglycerols in greater detail than the mass spectra of other acylglycerol derivatives.

The positions of methyl branches and epoxy and cyclopropyl rings in mono-and diacylglycerols can he determined from characteristic features in the fragmentation patterns, which are caused by radical-induced cleavage of the alkyl chains following random hydrogen abstraction by the pyridine nucleus. These results offer a promising approach to the structural analysis of glycerophospholipids by means of GC/MS.