Enantiomeric differentiation of β‐amino alcohols under electrospray ionization mass spectrometric conditions |
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| Authors: | R. Karthikraj Ramesh Kumar Chitumalla Kotamarthi Bhanuprakash S. Prabhakar M. Vairamani |
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| Affiliation: | 1. National Centre for Mass Spectrometry, CSIR‐Indian Institute of Chemical Technology, , Hyderabad, 500007 A.P., India;2. Inorganic and Physical chemistry division, CSIR‐Indian Institute of Chemical Technology, , Hyderabad, 500007 A.P., India;3. School of Bio‐Engineering, SRM University, , Chennai, 603203 T.N., India |
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| Abstract: | The enantiomeric differentiation of a series of chiral β‐amino alcohols (A) is attempted, for the first time, by applying the kinetic method using L‐proline, L‐tryptophan, 4‐iodo‐L‐phenylalanine or 3, 5‐diiodo‐L‐tyrosine as the chiral references (Ref) and Cu2+ or Ni2+ ion (M) as the central metal ion. The trimeric diastereomeric adduct ions, [M+(Ref)2+A‐H]+, formed under electrospray ionization conditions, are subjected for collision‐induced dissociation (CID) experiments. The products ions, formed by the loss of either a reference or an analyte, detected in the CID spectra are evaluated for the enantiomeric differentiation. All the references showed enantiomeric differentiation and the Rchiral values are better for the aromatic alcohols than for aliphatic alcohols. Notably, the Rchiral values of the aliphatic amino alcohols enhanced when Ni2+ is used as the central metal ion. The experimental results are well supported by computational studies carried out on the diastereomeric dimeric complexes. The computational data of amino alcohols is correlated with that of amino acids to understand the structural interaction of amino alcohols with reference molecule and central metal ion and their role on the stabilization of the dimeric complexes. Application of flow injection MS/MS method is also demonstrated for the enantiomeric differentiation of the amino alcohols. Copyright © 2014 John Wiley & Sons, Ltd. |
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| Keywords: | amino alcohols enantiomeric differentiation collision‐induced dissociation Cooks' kinetic method electrospray ionization mass spectrometry |
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