Diastereoselective fragmentation of chiral α-aminophosphonic acids/metal ion aggregates

TitoloDiastereoselective fragmentation of chiral α-aminophosphonic acids/metal ion aggregates
Tipo di pubblicazioneArticolo su Rivista peer-reviewed
Anno di Pubblicazione2006
AutoriFilippi, A., Speranza M., Paladini A., De Carolis R., Guidoni A.G., Laganà A., and Satta M.
RivistaJournal of Mass Spectrometry
Parole chiave(1 aminopropyl)phosphonic acid, Amino acids, article, Chemical composition, Chiral discrimination, Chirality, Cluster fragmentation, collisionally activated dissociation, complex formation, diastereoisomer, Dissociation, fragmentation reaction, Gas, Lithium compounds, Mass Spectrometry, metal ion, Metal ion aggregates, Nickel compounds, phosphoramidic acid, priority journal, Quadrupole mass spectrometry, Silver compounds, Sodium compounds, unclassified drug

Diastereomeric clusters of general formula [MAB2]+ and [MA2B]+ (M = Li(I), Na(I), Ag(I), Ni(II)-H, or Cu(II)-H; A = (R)-(-)- and (S)-(+)-(1-aminopropyl)phosphonic acid; B = (1R)-(-)- and (1S)-(+)-(1-aminohexyl)phosphonic acid) have been readily generated in the electrospray ionization (ESI) source of a triple-quadrupole mass spectrometer and their collision-induced dissociation (CID) investigated. CID of diastereomeric complexes, e.g. [MAS(BS)2] + and [MAR(BS)2]+, leads to fragmentation patterns characterized by Rhomo = [MA SBS]+/[M(BS)2] + and Rhetero = [MARBS] +/[M(BS)2]+ abundance ratios, which depend upon the relative stability of the diastereomeric [MASB S]+ and [MARBS]+ complexes in the gas phase. The chiral resolution factor Rchiral = Rhomo/Rhetero is found to depend not only on the nature of the M ion but also on that of the fragmenting species, whether [MAB 2]+ or [MA2B]+. The origin of this behavior is discussed. Copyright © 2005 John Wiley & Sons, Ltd.


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