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Volumn 47, Issue 18, 2008, Pages 3461-3463

Influence of amino acid side chains on long-distance electron transfer in peptides: Electron hopping via "stepping stones"

Author keywords

Aromatic amino acids; Electron hopping; Electron transfer; Peptides

Indexed keywords

AMINES; AMINO ACIDS; CHEMICAL REACTIONS; ELECTRON TRANSITIONS; ORGANIC ACIDS; PEPTIDES; PROTEINS;

EID: 43849113277     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705588     Document Type: Article
Times cited : (116)

References (28)
  • 4
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    • Refinement of this model, by taking protein dynamics into account, enabled good agreement with the experimental data (Refs. [1,2]) to be achieved: T. R. Prytkova, I. V. Kurnikov, D. N. Beratan, Science 2007, 315, 622;
    • Refinement of this model, by taking protein dynamics into account, enabled good agreement with the experimental data (Refs. [1,2]) to be achieved: T. R. Prytkova, I. V. Kurnikov, D. N. Beratan, Science 2007, 315, 622;
  • 6
    • 53549123395 scopus 로고    scopus 로고
    • for further recent contributions on the influence of backbone conformations on electronic coupling, see
    • for further recent contributions on the influence of backbone conformations on electronic coupling, see E. W. Schlag, S .-Y. Sheu, D.-Y. Yang, H. L. Selzle, S. H. Lin, Angew. Chem. 2007, 119, 3258;
    • (2007) Angew. Chem , vol.119 , pp. 3258
    • Schlag, E.W.1    Sheu, S.-Y.2    Yang, D.-Y.3    Selzle, H.L.4    Lin, S.H.5
  • 10
    • 5644228647 scopus 로고    scopus 로고
    • For further experiments in which a charge hopping through side chains or peptide bonds are discussed, see K. Yanagisawa, T. Morita, S. Kimura, J. Am. Chem. Soc. 2004, 126, 12780;
    • For further experiments in which a charge hopping through side chains or peptide bonds are discussed, see K. Yanagisawa, T. Morita, S. Kimura, J. Am. Chem. Soc. 2004, 126, 12780;
  • 16
    • 53549099234 scopus 로고    scopus 로고
    • The enantioselective syntheses of the new aromatic amino acids follow the Erlenmeyer-azlactone synthesis and are reported in: M. Cordes, O. Jacques, A. Köttgen, C. Jasper, H. Boudebous, B. Giese, Adv. Synth. Catal., in press.
    • The enantioselective syntheses of the new aromatic amino acids follow the Erlenmeyer-azlactone synthesis and are reported in: M. Cordes, O. Jacques, A. Köttgen, C. Jasper, H. Boudebous, B. Giese, Adv. Synth. Catal., in press.
  • 17
    • 12944281484 scopus 로고    scopus 로고
    • The CD spectra of compounds 1a-d, 6, and 7 show a negative band around 206 nm and a positive band around 229 nm, which are characteristic of a PPII helix. The helices do not melt upon heating to 80°C. The PPII helix has a repeat unit of three proline molecules with an axial translation of 3.2 Å per residue, see, for example: S. Kakinoki, Y. Hirano, M. Oka, Polym. Bull. 2005, 53, 109. In an ideal PPII helix, the side chains of the donor, acceptor, and relay amino acids in compounds 1a-d will be at an angle of 120° to each other.
    • The CD spectra of compounds 1a-d, 6, and 7 show a negative band around 206 nm and a positive band around 229 nm, which are characteristic of a PPII helix. The helices do not melt upon heating to 80°C. The PPII helix has a repeat unit of three proline molecules with an axial translation of 3.2 Å per residue, see, for example: S. Kakinoki, Y. Hirano, M. Oka, Polym. Bull. 2005, 53, 109. In an ideal PPII helix, the side chains of the donor, acceptor, and relay amino acids in compounds 1a-d will be at an angle of 120° to each other.
  • 18
    • 0032539233 scopus 로고    scopus 로고
    • We have already used and studied a similar system for the injection of a positive charge into the heterocyclic bases of DNA: E. Meggers, M. E. Michel-Beyerle, B. Giese, J. Am. Chem. Soc. 1998, 120, 12950;
    • We have already used and studied a similar system for the injection of a positive charge into the heterocyclic bases of DNA: E. Meggers, M. E. Michel-Beyerle, B. Giese, J. Am. Chem. Soc. 1998, 120, 12950;
  • 21
    • 53549088173 scopus 로고    scopus 로고
    • Degassed solutions of 1a-d, 6, and 7 (5 mm in acetonitrile/water 3:1) were irradiated at a wavelength of 308 nm in a quartz cell of 4.5 cm path length with a Lambda-Physik COMPex 205 laser (pulse width: 25 ns, 100-150 mJ per pulse) at RT. An iStar 720 ICCD camera (Andor) was used for the detection of transient absorption spectra 40 ns after irradiation. The signals of five flashes were accumulated to improve the signal/noise ratios.
    • Degassed solutions of 1a-d, 6, and 7 (5 mm in acetonitrile/water 3:1) were irradiated at a wavelength of 308 nm in a quartz cell of 4.5 cm path length with a Lambda-Physik COMPex 205 laser (pulse width: 25 ns, 100-150 mJ per pulse) at RT. An iStar 720 ICCD camera (Andor) was used for the detection of transient absorption spectra 40 ns after irradiation. The signals of five flashes were accumulated to improve the signal/noise ratios.
  • 22
    • 53549120754 scopus 로고    scopus 로고
    • -1. Therefore, UV detection of the intermediates before 40 ns is not useful.
    • -1. Therefore, UV detection of the intermediates before 40 ns is not useful.
  • 28
    • 53549098675 scopus 로고    scopus 로고
    • The oxidation potentials of the aromatic amino acids were measured in acetonitrile by differential pulse voltammetry with ferrocene as an internal standard (working electrode: glassy carbon,(TBA)PF6 as electrolyte (TBA, tetrabutylammonium, scan rate 100 mVs-1, N-Ac-2,4-dimethoxyphenylalanine methyl ester 0.95 V; N-Ac-2,4,6- trimethoxyphenylalanine methyl ester 0.94 V; N-Ac-tyrosine methyl ester 0.85 V (versus the ferrocene/ferrocinium Fc/Fc, couple
    • +) couple).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.