Fast atom bombardment and collisional activation mass spectrometry of retinyl phosphate mannose synthesized by liver membranes.
Fast atom bombardment (FAB) and collisional activation dissociation (CAD) mass-analysed ion kinetic energy (MIKE) spectra have confirmed the structures of retinyl phosphate (Ret-P), retinyl phosphate mannose (Ret-P-Man) and guanosine 5'-diphospho-D-mannose (GDP-Man). Ret-P-Man was made in vitro while Ret-P and GDP-Man were chemically synthesized. Positive ion FAB mass spectrometry of Ret-P showed an observable short-lived spectrum with a mass ion at m/z 367 [M + H]+, and a major fragment ion at m/z 269 [M + H - H3PO4]+. Negative ion FAB mass spectrometry of Ret-P showed a strong stable spectrum with a parent ion at m/z 365 [M - H]-, a glycerol (G) adduct ion at m/z 457 [M - H + G]- and a dimer ion at m/z 731 [2M - H]-. GDP-Man showed an intense spectrum with parent ion at m/z 604 [M - H]- and cationized species at m/z 626 [M + Na - 2H]- and 648 [M + 2Na - 3H]-. Negative ion FAB mass spectrometry of Ret-P-Man showed a parent ion at m/z 527 [M - H]- and a fragment ion at m/z 259 [C6H12PO9]-. The CAD-MIKE spectra showed structurally significant fragment ions at m/z 442 and 361 for the [M - H]- ion of GDP-Man, and at m/z 509, 406, 364 and 241 for the [M - H]- ion of Ret-P-Man. FAB and CAD-MIKE spectra have been applied successfully to confirm the structure of Ret-P-Man made in vitro from Ret-P and GDP-Man.
Clifford
A J
AJ
Silverman-Jones
C S
CS
Creek
K E
KE
De Luca
L M
LM
Tondeur
Y
Y
D000818:Animals; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004224:Diterpenes; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism*; D013058:Mass Spectrometry; D008566:Membranes / Q000378:metabolism; D011103:Polyisoprenyl Phosphate Monosaccharides / Q000096:biosynthesis*; D011105:Polyisoprenyl Phosphate Sugars / Q000096:biosynthesis*; D051381:Rats
D004224:Diterpenes; D011103:Polyisoprenyl Phosphate Monosaccharides; D011105:Polyisoprenyl Phosphate Sugars; C013101:mannosylretinylphosphate