Mass spectrometric and quantum-chemical study on the structure, stability, and chirality of protonated serine dimers

Ferenc Pollreisz, A. Gömöry, G. Schlosser, K. Vékey, Iván Solt, A. Császár

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9 Citations (Scopus)

Abstract

Stability and structure of homo- and heterochiral protonated serine (Ser) dimers were investigated by a combination of mass spectrometry and ab initio quantum chemical calculations. This established that the energy difference between the most stable homo- and heterochiral forms is very small: tandem mass spectrometry with Cooks' kinetic method yielded a negligible difference in Gibbs free energy (0.2 ± 0.2 kJ mol 1). The various isomeric forms of (Ser)2H+ and their energetics were determined by extensive electronic-structure calculations, which yielded homo- and heterochiral forms of the isomers with distinctly different relative energies. The most stable homochiral isomer is stabilized by two hydrogen bonds and is far more stable than any other homochiral isomer. The most stable heterochiral isomer has completely different features, and it is characterized by a salt-bridge structure. This clearly shows that salt-bridge structures do exist in the gas phase even in comparatively small molecules and in the absence of particularly basic or acidic functional groups.

Original languageEnglish
Pages (from-to)5908-5916
Number of pages9
JournalChemistry - A European Journal
Volume11
Issue number20
DOIs
Publication statusPublished - Oct 7 2005

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Chirality
Isomers
Dimers
Serine
Mass spectrometry
Salts
Gibbs free energy
Functional groups
Electronic structure
Hydrogen bonds
Gases
Molecules
Kinetics

Keywords

  • Amino acids
  • Chirality
  • Focal-point analysis
  • Hydrogen bonds
  • Mass spectrometry

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "Stability and structure of homo- and heterochiral protonated serine (Ser) dimers were investigated by a combination of mass spectrometry and ab initio quantum chemical calculations. This established that the energy difference between the most stable homo- and heterochiral forms is very small: tandem mass spectrometry with Cooks' kinetic method yielded a negligible difference in Gibbs free energy (0.2 ± 0.2 kJ mol 1). The various isomeric forms of (Ser)2H+ and their energetics were determined by extensive electronic-structure calculations, which yielded homo- and heterochiral forms of the isomers with distinctly different relative energies. The most stable homochiral isomer is stabilized by two hydrogen bonds and is far more stable than any other homochiral isomer. The most stable heterochiral isomer has completely different features, and it is characterized by a salt-bridge structure. This clearly shows that salt-bridge structures do exist in the gas phase even in comparatively small molecules and in the absence of particularly basic or acidic functional groups.",
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T1 - Mass spectrometric and quantum-chemical study on the structure, stability, and chirality of protonated serine dimers

AU - Pollreisz, Ferenc

AU - Gömöry, A.

AU - Schlosser, G.

AU - Vékey, K.

AU - Solt, Iván

AU - Császár, A.

PY - 2005/10/7

Y1 - 2005/10/7

N2 - Stability and structure of homo- and heterochiral protonated serine (Ser) dimers were investigated by a combination of mass spectrometry and ab initio quantum chemical calculations. This established that the energy difference between the most stable homo- and heterochiral forms is very small: tandem mass spectrometry with Cooks' kinetic method yielded a negligible difference in Gibbs free energy (0.2 ± 0.2 kJ mol 1). The various isomeric forms of (Ser)2H+ and their energetics were determined by extensive electronic-structure calculations, which yielded homo- and heterochiral forms of the isomers with distinctly different relative energies. The most stable homochiral isomer is stabilized by two hydrogen bonds and is far more stable than any other homochiral isomer. The most stable heterochiral isomer has completely different features, and it is characterized by a salt-bridge structure. This clearly shows that salt-bridge structures do exist in the gas phase even in comparatively small molecules and in the absence of particularly basic or acidic functional groups.

AB - Stability and structure of homo- and heterochiral protonated serine (Ser) dimers were investigated by a combination of mass spectrometry and ab initio quantum chemical calculations. This established that the energy difference between the most stable homo- and heterochiral forms is very small: tandem mass spectrometry with Cooks' kinetic method yielded a negligible difference in Gibbs free energy (0.2 ± 0.2 kJ mol 1). The various isomeric forms of (Ser)2H+ and their energetics were determined by extensive electronic-structure calculations, which yielded homo- and heterochiral forms of the isomers with distinctly different relative energies. The most stable homochiral isomer is stabilized by two hydrogen bonds and is far more stable than any other homochiral isomer. The most stable heterochiral isomer has completely different features, and it is characterized by a salt-bridge structure. This clearly shows that salt-bridge structures do exist in the gas phase even in comparatively small molecules and in the absence of particularly basic or acidic functional groups.

KW - Amino acids

KW - Chirality

KW - Focal-point analysis

KW - Hydrogen bonds

KW - Mass spectrometry

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