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Volumn 111, Issue 2, 2007, Pages 485-489

Density functional theory methods as powerful tools to elucidate amino acid oxidation mechanisms. A case study on methionine model peptide

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATION THEORY; OXIDATION; PROBABILITY DENSITY FUNCTION; PROTONS; REACTION KINETICS; TIME DOMAIN ANALYSIS;

EID: 84962449685     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp066443s     Document Type: Article
Times cited : (12)

References (58)
  • 35
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    • Lide, D. R, Ed, CRC Press: Boca Raton, FL
    • Lide, D. R., Ed. CRC Handbook of Chemistry and Physics; CRC Press: Boca Raton, FL, 2002.
    • (2002) CRC Handbook of Chemistry and Physics
  • 44
    • 84962364193 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Zakrzewski, V. G, Montgomery, J. A, Stratmann, R. E, Burant, J. C, Dapprich, S, Millam, J. M, Daniels, A. D, Kudin, K. N, Strain, M. C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Salvador, P, Dannenberg, J. J, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Baboul, A. G, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaroni, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nanayakkara, A, Challacombe, M, Gill, P. M. W, Johnson, B, Chen, W, Wong, M. W, Andres, J. L, Gonzalez, C, Head-Gordon, M, Replogle, E. S, Pople, J. A. Gaussian 98, revision A.11, Gaussian, Inc, Pittsburgh, PA, 2001
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaroni, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11, Gaussian, Inc.: Pittsburgh, PA, 2001.
  • 45
    • 84962470332 scopus 로고    scopus 로고
    • The Gaussian 03 program was also employed to do calculations. Both programs give identical energetic parameters and similar absorption spectra. For instance, the Gaussian 03-derived absorption peaks for 4, 6, 8, 9, 11, and 12 are 278, 405, 446, 440, 395, 266 (and 312) nm, respectively. However, Gaussian 03 failed to calculate spectra of molecules 2 and 5. Therefore, Gaussian 98 is preferentially selected.
    • The Gaussian 03 program was also employed to do calculations. Both programs give identical energetic parameters and similar absorption spectra. For instance, the Gaussian 03-derived absorption peaks for 4, 6, 8, 9, 11, and 12 are 278, 405, 446, 440, 395, 266 (and 312) nm, respectively. However, Gaussian 03 failed to calculate spectra of molecules 2 and 5. Therefore, Gaussian 98 is preferentially selected.
  • 46
    • 84962395011 scopus 로고    scopus 로고
    • The addition reaction of 1 is thermodynamically favored with a ΔH value of -10.29 kcal/mol.
    • The addition reaction of 1 is thermodynamically favored with a ΔH value of -10.29 kcal/mol.
  • 47
    • 84962470375 scopus 로고    scopus 로고
    • The overlap electronic density was calculated according to the second term of the right part of eq 1
    • The overlap electronic density was calculated according to the second term of the right part of eq 1.
  • 48
    • 84962464867 scopus 로고    scopus 로고
    • In fact, the structures containing the S-N bond cannot be optimized
    • In fact, the structures containing the S-N bond cannot be optimized.
  • 49
    • 84962464871 scopus 로고    scopus 로고
    • The cyclization processes are exoergic, with ΔH values of -8.07 and -9.48 kcal/mol for reactions 3 → 6 and 3 → 9, respectively.
    • The cyclization processes are exoergic, with ΔH values of -8.07 and -9.48 kcal/mol for reactions 3 → 6 and 3 → 9, respectively.
  • 50
    • 84962470389 scopus 로고    scopus 로고
    • The predicted absorption peak of 440 nm is in accordance with an earlier theoretical estimation, 453 nm.27b
    • 27b
  • 52
    • 84962470364 scopus 로고    scopus 로고
    • It should be pointed out that in 11, a S-O bond still exists although is rather weak, with an overlap electronic density of 0.02, which is weaker than the S-N bond, which holds an overlap electronic density of 0.06
    • It should be pointed out that in 11, a S-O bond still exists (although is rather weak), with an overlap electronic density of 0.02, which is weaker than the S-N bond, which holds an overlap electronic density of 0.06.
  • 55
    • 84962470379 scopus 로고    scopus 로고
    • 31c
    • 31c


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.