Structural determination of cyclitol derivatives by fast-atom bombardment tandem mass spectrometry.
Three cyclitol derivatives were isolated from the marine sponge Sarcotragus sp. by reversed-phase high-performance liquid chromatography and analyzed by fast-atom bombardment mass spectrometry (FAB-MS). Their structural elucidation was carried out with FAB tandem mass spectrometry (FAB-MS/MS). FAB-MS spectra produced a significant abundance of the sodium adducts [M+Na]+ and [M+2Na-H]+ from a mixture of m-NBA and NaI. In addition, trifluoroacetylation of the cyclitol derivatives was used for confirmation of the presence of the cyclitol ring. High abundance [M-5H+5CF3CO+Na]+ ions were observed in the FAB-MS spectra of the trifluoroacetyl-cyclitol derivatives. Collision-induced dissociation (CID) of the [M+Na]+ ions produced diverse product ions via a series of dissociative processes. Charge-remote fragmentation (CRF) patterns of [M+Na]+ ions were very useful for the identification of product ions which are characteristic for the cyclitol ring and long hydrocarbon chains substituted at the glycerol backbone. Moreover, the CID-MS/MS spectra of the [M+Na]+ ions yielded characteristic product ions at m/z 53, 83, 113, 155 and 171 for the cyclitol moiety, and at m/z 213, 229 and 245 for the glycerol backbone attached to the cyclitol ring.
Gil
Ji Hye
JH
Hazardous Substance Research Team, Korea Basic Science Institute, Seoul 136-701, Korea.
Seo
JungJu
J
Kim
Kang-Jin
KJ
Jung
Jee H
JH
Jung
Ok-Sang
OS
Kim
Min-Sun
MS
Hong
Jongki
J
D000818:Animals; D003516:Cycloparaffins / Q000737:chemistry* / Q000302:isolation & purification; D011161:Porifera / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014269:Trifluoroacetic Acid / Q000737:chemistry
D003516:Cycloparaffins; D014269:Trifluoroacetic Acid