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Article Dans Une Revue International Journal of Mass Spectrometry Année : 2012

Origin of enantioselective reduction of quaternary copper D,L amino acid complexes under vibrational activation conditions

Résumé

Phenylglycine (Phg), a non natural amino acid was used as chiral selector for the distinction of L/D amino acids through enantioselective Cu(II) redn. The investigation of the chiral effects was performed based on the dissocn. of copper quaternary complexes involving phenylglycine: [Cu(II),(Phg,AA1,AA2-H)]+. The main cleavage was the competitive formal loss of Phg and [Phg-H]* yielding the [Cu(II),(AA1,AA2-H)]+ and [Cu(I),(AA1,AA2)]+ ions resp. The later involving a stepwise process with CO2 loss and a concomitant Cu(II) redn. The relative extent of this competitive process appeared to be strongly enantioselective. This led the authors to explore the origin of the obsd. enantiomeric redn. from dissocns. of copper-AA complexes. With this aim, smaller [Cu(II),(Phg,AA-H)]+ ternary complexes have been investigated and MSn together with double resonance-IRMPD expts. have been conducted. The existence of zwitterions was considered in order explain the role of gas phase acidity and proton affinity on the enantioselective redn.

Dates et versions

hal-00708852 , version 1 (15-06-2012)

Identifiants

Citer

Carlos Afonso, Denis Lesage, Francoise Fournier, Valérie Mancel, Tabet Jean-Claude. Origin of enantioselective reduction of quaternary copper D,L amino acid complexes under vibrational activation conditions. International Journal of Mass Spectrometry, 2012, 312, pp.185-194. ⟨10.1016/j.ijms.2011.08.011⟩. ⟨hal-00708852⟩
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