Competition between salt bridge and non-zwitterionic structures in deprotonated amino acid dimers

Physical Chemistry Chemical Physics : PCCP
S HeilesEvan R Williams

Abstract

Structures of deprotonated Cys, Asp, Glu, Phe, Pro, His homo dimers as well as [2Cys - 3H]-, [Asp + Glu - H]- and [2Glu - 2H + Na]- are investigated with infrared multiple-photon dissociation (IRMPD) spectroscopy between 650 and 1850 cm-1 and theory. The IRMPD spectra of all investigated complexes but [2His - H]-, [2Phe - H]- and [2Pro - H]- indicate that the structures consist of a neutral non-zwitterionic (NZ) and a deprotonated form of the amino acids. In contrast, the spectrum of [2His - H]- is complex and indicates the presence of multiple isomers and/or interactions between His and [His - H]-, so that its structure differs from that of the other deprotonated amino acid dimers. For [2Phe - H]- and especially for [2Pro - H]-, some IRMPD bands can only be explained by the presence of salt bridge (SB) structures in the dimer in which a deprotonated amino acid interacts with a zwitterionic neutral amino acid. Computational results indicate that SB structures are lower in energy at 298 K than corresponding NZ structures for neutral-anion complexes in which SB formation is not disrupted by amino acid side chains or conformational constraints, such as in [2Glu - H]- and [2Cys - 3H]- for which NZ structures are most consistent wit...Continue Reading

References

Feb 1, 1995·Nature Structural Biology·C D WaldburgerR T Sauer
Jan 1, 1997·Annual Review of Physical Chemistry·C L Perrin, J B Nielson
Feb 8, 2003·Science·Knut R AsmisLudger Wöste
Feb 15, 2003·Journal of the American Society for Mass Spectrometry·Dunmin Mao, D J Douglas
Feb 12, 2004·Journal of the American Chemical Society·Catherine KapotaGilles Ohanessian
Feb 26, 2005·Chemical Reviews·Michael Meot-Ner
Mar 18, 2005·Journal of the American Chemical Society·Han-Bin OhFred W McLafferty
Jan 13, 2006·Journal of the American Chemical Society·Nick C PolferRobert C Dunbar
Feb 16, 2006·Journal of the American Chemical Society·W D PriceE R Williams
Apr 8, 2006·The Journal of Physical Chemistry. B·Christopher F RodriquezK W Michael Siu
Oct 13, 2007·Journal of the American Chemical Society·Matthew F BushEvan R Williams
Nov 2, 2007·The Journal of Physical Chemistry. a·Matthew W ForbesRebecca A Jockusch
Mar 28, 2008·The Journal of Physical Chemistry. a·Jos Oomens, Jeffrey D Steill
May 1, 2008·Journal of the American Chemical Society·Matthew F BushEvan R Williams
Nov 8, 2008·Physical Chemistry Chemical Physics : PCCP·Jeng-Da Chai, Martin Head-Gordon
Mar 10, 2009·Journal of the American Chemical Society·Jos OomensBritta Redlich
Jul 25, 2009·Journal of the American Chemical Society·James S PrellEvan R Williams
Sep 29, 2011·Journal of the American Society for Mass Spectrometry·Christopher M LeavittMark A Johnson
Sep 29, 2011·Journal of the American Society for Mass Spectrometry·Ronghu WuTerry B McMahon
Apr 25, 2012·Journal of the American Society for Mass Spectrometry·Georgios PapadopoulosThomas R Rizzo
Jun 20, 2012·Journal of the American Chemical Society·Ulrich J Lorenz, Thomas R Rizzo
Aug 10, 2012·Chemical Reviews·Michael Meot-Ner Mautner
May 28, 2013·The Journal of Physical Chemistry. a·Robert C DunbarK W Michael Siu
Feb 6, 2014·Journal of the American Society for Mass Spectrometry·Zhe ZhangRichard W Vachet

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Citations

Nov 2, 2021·Journal of the American Society for Mass Spectrometry·Simon BecherSven Heiles

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