Chiral recognition in solution and the gas phase. Experimental and theoretical studies of aromatic D- and L-amino acid-Cu(II)-chiragen complexes

Journal of Mass Spectrometry : JMS
Jennifer L SeymourPavel Kocovský

Abstract

This study was focused on distinguishing L- and D-enantiomers of amino acids using electrospray ionization mass spectrometry (ESI-MS) of ternary complexes with Cu(II) and chiral derivatives of bipyridine. A pinene-annulated derivative of 2,2'-bipyridine, (5R,7S,8S)-(--)-5,6,7,8-tetrahydro-6,6,8-trimethyl-2-(pyridin-2-yl)-5,7-methanoquinoline, called a chiragen, was used as the auxiliary ligand bound to Cu(II) to study the complexation of D- and L-phenylalanine and D- and L-tryptophan and their detection by MS. NMR studies showed that the D- and L-amino acid complexes can be distinguished in solution by the difference in the amount of band broadening of the alpha-carbon proton, with the D-complex showing greater broadening from a more intense interaction with the paramagnetic copper center. In ESI-MS studies, the ion abundances for the analyte complexes were compared with those of internal standards to investigate competition in binding to Cu(II)chiragen between the internal standard and D- and L-amino acids. The D-Phe complex showed stronger binding than the L-Phe complex, although differences in response related to solvent effects were also apparent. In studies involving two separate internal standards, the Trp enantiomers wer...Continue Reading

Citations

Jun 26, 2007·Journal of the American Society for Mass Spectrometry·Sangeeta KumariKotamarthi Bhanuprakash
Oct 25, 2008·Journal of the American Society for Mass Spectrometry·Anna R M HyyryläinenPirjo Vainiotalo
May 3, 2007·Mass Spectrometry Reviews·Frantisek Turecek
Jan 16, 2007·Chemical Communications : Chem Comm·Maddula RavikumarMariappanadar Vairamani
Nov 9, 2004·Journal of Mass Spectrometry : JMS
Nov 19, 2017·Journal of Mass Spectrometry : JMS·Aleš MarekFrantišek Tureček
Mar 19, 2013·Physical Chemistry Chemical Physics : PCCP·Petr MilkoKarel Lemr
May 2, 2008·The Journal of Organic Chemistry·Andrei V MalkovPavel Kocovský

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