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Volumn 129, Issue 17, 2007, Pages 5403-5407

Are carboxyl groups the most acidic sites in amino acids? Gas-phase acidity, H/D exchange experiments, and computations on cysteine and its conjugate base

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CARBOXYLATION; DENSITY FUNCTIONAL THEORY; DEUTERIUM; FOURIER TRANSFORMS; MASS SPECTROMETERS;

EID: 34247877609     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0666194     Document Type: Article
Times cited : (77)

References (36)
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    • Additional data on valine, isoleucine, leucine, and methionine were cited in ref 1 and can be found in: Locke, M. J. Ph.D. Thesis, University of California, Irvine, CA, 1981.
    • Additional data on valine, isoleucine, leucine, and methionine were cited in ref 1 and can be found in: Locke, M. J. Ph.D. Thesis, University of California, Irvine, CA, 1981.
  • 4
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    • Mallard, W. G, Linstrom, P. J, Eds, National Institute of Standards and Technology: Gaithersburg, MD 20899
    • Bartmess, J. E. NIST Chemistry WebBook, NIST Standard Reference Database Number 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD 20899 (http://webbook.nist.gov).
    • NIST Chemistry WebBook, NIST Standard Reference Database Number 69
    • Bartmess, J.E.1
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    • 34247878327 scopus 로고    scopus 로고
    • Reed, D. R. Ph.D. Thesis, University of Minnesota, Minneapolis, MN, 2001.
    • Reed, D. R. Ph.D. Thesis, University of Minnesota, Minneapolis, MN, 2001.
  • 10
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    • Bowers, M. T, Ed, Academic Press: New York
    • Bartmess, J. E.; McIver, R. T., Jr. In Gas Phase Ion Chemistry; Bowers, M. T., Ed.; Academic Press: New York, 1979; Vol. 2, pp 87-121.
    • (1979) Gas Phase Ion Chemistry , vol.2 , pp. 87-121
    • Bartmess, J.E.1    McIver Jr., R.T.2
  • 23
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    • Gaussian, Inc, Pittsburgh, PA
    • Pople, J. A.; et al. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003.
    • (2003) Gaussian 03
    • Pople, J.A.1
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    • PCModel, version 8.5; Serena Software: Bloomington, IN, 2003.
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    • 34247864427 scopus 로고    scopus 로고
    • Low-energy C-N rotamers for 2, 3, and 9 are provided in the Supporting Information.
    • Low-energy C-N rotamers for 2, 3, and 9 are provided in the Supporting Information.
  • 30
    • 34247867055 scopus 로고    scopus 로고
    • -1) computations.
    • -1) computations.
  • 31
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    • 2nd ed, Worth Publishers: New York
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    • (1975) Biochemistry , pp. 79
    • Lehninger, A.L.1
  • 32
    • 33846081923 scopus 로고    scopus 로고
    • During the review process a photoelectron spectrum of the M - 1 ion of cysteine produced by electrospray ionization appeared which indicates the presence of a sulfur anion: Woo, H.-K.; Lau, K.-C.; Wang, X.-B.; Wang, L.-S. J. Phys. Chem. A 2006, 110, 12603-12606.
    • During the review process a photoelectron spectrum of the M - 1 ion of cysteine produced by electrospray ionization appeared which indicates the presence of a sulfur anion: Woo, H.-K.; Lau, K.-C.; Wang, X.-B.; Wang, L.-S. J. Phys. Chem. A 2006, 110, 12603-12606.
  • 33
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    • -1 from the G3B3 acidity, but this was not done, and the directly computed value is given.
    • -1 from the G3B3 acidity, but this was not done, and the directly computed value is given.
  • 35
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    • For a description of different hydrogen-deuterium exchange pathways, see
    • For a description of different hydrogen-deuterium exchange pathways, see: Campbell, S.; Rodgers, M. T.; Marzluff, E. M.; Beauchamp, J. L. J. Am. Chem. Soc. 1995, 117, 12840-12854.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 12840-12854
    • Campbell, S.1    Rodgers, M.T.2    Marzluff, E.M.3    Beauchamp, J.L.4
  • 36
    • 34247858129 scopus 로고    scopus 로고
    • An error of ±2 eu was assumed for ΔS0 acid, and a similar value of 23.8 is obtained using B3LYP/6-31G(d) geometries and unsealed vibrational frequencies. If the kADO rate is used instead of k-1 in determining the acidity, the reported value is unaffected
    • -1 in determining the acidity, the reported value is unaffected.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.