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Volumn 110, Issue 5, 2006, Pages 1718-1725

Electron-transfer oxidation properties of unsaturated fatty acids and mechanistic insight into lipoxygenases

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON-TRANSFER OXIDATION; LASER FLASH PHOTOLYSIS; UNSATURATED FATTY ACIDS;

EID: 33644779089     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp054648f     Document Type: Article
Times cited : (34)

References (90)
  • 34
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    • Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany
    • Hammes-Schiffer, S. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 189-237.
    • (2001) Electron Transfer in Chemistry , vol.1 , pp. 189-237
    • Hammes-Schiffer, S.1
  • 39
    • 0024538444 scopus 로고
    • et) of oxidation of arachidonic acid and cyclohexene with cerium(IV) ammonium nitrate; see: Wiseman, J. S. Biochemistry 1989, 28, 2106.
    • (1989) Biochemistry , vol.28 , pp. 2106
    • Wiseman, J.S.1
  • 40
    • 0001504721 scopus 로고
    • et and the reduction potentials of Ce(IV) as reported for the electron-transfer oxidation of olefins by iron-(III) complexes (Fukuzumi, S.; Kochi, J. K. J. Am. Chem. Soc. 1982, 104, 7599)
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 7599
    • Fukuzumi, S.1    Kochi, J.K.2
  • 41
    • 33947090337 scopus 로고
    • -1) for the electron-transfer oxidation of arachidonic acid with Ce(IV) certainly indicates that the electron-transfer process is coupled with the subsequent deprotonation process of the resulting radical cation, when the electron transfer is not the sole rate-determining step.
    • (1972) J. Org. Chem. , vol.37 , pp. 916
    • Miller, L.L.1    Nordblom, G.D.2    Maeda, E.A.3
  • 59
    • 0000487132 scopus 로고    scopus 로고
    • Jortner, J., Bixon, M., Eds.; John Wiley & Sons: New York
    • 41-42 the application to analyze intermolecular electron-transfer reactions has been limited because of the change in the reorganization energy of intermolecular electron-transfer reactions, which varies depending on the driving force of electron transfer. See: (a) Malaga, N.; Miyasaka, H. In Electron Transfer-From Isolated Molecules to Biomolecules; Jortner, J., Bixon, M., Eds.; John Wiley & Sons: New York, 1999. Part 2, p 431.
    • (1999) Electron Transfer-from Isolated Molecules to Biomolecules , Issue.2 PART , pp. 431
    • Malaga, N.1    Miyasaka, H.2
  • 65
    • 84955395805 scopus 로고    scopus 로고
    • Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany
    • (b) Fukuzumi, S.; Guldi, D. M. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 270-337.
    • (2001) Electron Transfer in Chemistry , vol.2 , pp. 270-337
    • Fukuzumi, S.1    Guldi, D.M.2
  • 66
    • 33644778347 scopus 로고    scopus 로고
    • note
    • The work terms required to bring the products and the reactants of cation sensitizers together to the mean separation in the precursor complex are zero, because both the reactants and products include neutral species. The work term for the products of neutral sensitizers in a highly polar solvent such as MeCN can also be neglected; see refs 38, 39, and 41.
  • 71
    • 33644771874 scopus 로고    scopus 로고
    • note
    • +* because the electron-transfer processes would be endergonic. This shows sharp contrast to the results in Figure 4 and Figure 5.
  • 72
    • 33644786646 scopus 로고    scopus 로고
    • note
    • The first-order decay indicates that the deprotonation of linoleic acid radical cation involves the solvent. However, the residual water may also be involved in the deprotonation step.
  • 74
    • 33644771875 scopus 로고    scopus 로고
    • note
    • + indicates that the proton transfer occurs in the cage in competition with the escape from the cage. The rather slow escape rate from the cage indicates that there is π-π interaction between oleic radical cation and AcrHV.
  • 77
    • 33644783369 scopus 로고    scopus 로고
    • note
    • 1DCA* in contrast to the results in Figure 6.
  • 86
    • 33644785539 scopus 로고    scopus 로고
    • note
    • + in solution; see ref 49.
  • 87
    • 33644773202 scopus 로고    scopus 로고
    • note
    • red2.3RT (= 10.81, T = 298 K) in terms of logarithm of the rate constant. In such a case, an outersphere PCET pathway in the reaction of linoleic acid with Fe(III)-OH can be definitely ruled out.
  • 89
    • 33644755219 scopus 로고    scopus 로고
    • note
    • ox/RT); F is Faraday constant and T = 298 K.
  • 90
    • 33847087736 scopus 로고
    • For the distinction between outer-sphere and inner-sphere electron-transfer processes, see: Fukuzumi, S.; Wong. C. L.; Kochi, J. K. J. Am. Chem. Soc. 1980, 102, 2928.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 2928
    • Fukuzumi, S.1    Wong, C.L.2    Kochi, J.K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.