In situ formation of C-glycosides during electrospray ionization tandem mass spectrometry of a series of synthetic amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine.
In this communication, the structural analysis of six synthetic O-Linked amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine was performed by electrospray ionization mass spectrometry in the positive ion mode, with a QqTOF-MS/MS hybrid instrument. The MS/MS analyses provided evidence for the "in situ" formation, in the collision cell of the tandem mass spectrometer, of an unexpected and unique [C-glycoside]+ product ion, resulting from an ion-molecule reaction between the N-acetyl-D-glucosamine oxonium ion and the neutral cholesta-3,5-diene molecule. Quasi MS3 analysis of this ion resulted in the dissociation of the precursor [C-glycoside]+ ion, which produced the expected third generation N-acetyl-D-glucosamine oxonium and the protonated cholesta-3,5-diene product ions.
Banoub
Joseph
J
Department of Fisheries and Oceans, St. John's, Newfoundland, Canada. Banoubjo@dfo-mpo.gc.ca
Boullanger
Paul
P
Lafont
Dominique
D
Cohen
Alejandro
A
El Aneed
Anas
A
Rowlands
Elizabeth
E
D000117:Acetylglucosamine / Q000737:chemistry*; D006017:Glycolipids / Q000737:chemistry*; D006027:Glycosides; D057927:Hydrophobic and Hydrophilic Interactions; D008081:Liposomes / Q000737:chemistry; D009005:Monosaccharides / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
C438934:C-glycoside; D006017:Glycolipids; D006027:Glycosides; D008081:Liposomes; D009005:Monosaccharides; D000117:Acetylglucosamine