Photoinduced electron transfer between non-native donor-acceptor moieties incorporated in synthetic polypeptide aggregates

Organic Letters

Volumn 4, Issue 23, 2002, Pages 4001-4004

  Jones II, Guilford ^a   Vullev, Valentine I ^a,b  

^a BOSTON UNIVERSITY   (United States)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; ELECTRON TRANSPORT; LIGHT; PROTEIN CONFORMATION; RADIATION EXPOSURE; SYNTHESIS;

AMINO ACID SEQUENCE; CIRCULAR DICHROISM; ELECTRON TRANSPORT; INDICATORS AND REAGENTS; LIGHT; PEPTIDES; PROTEIN CONFORMATION;

EID: 0037078828     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026656+     Document Type: Article

References (34)

1. For reviews see: Vullev, V. I.; Jones, G, II. Res. Chem. Interm. In press. Ogawa, M. Y. Mol. Supramol. Photochem. 1999, 4, 113. Mutz, M. W.; Wishart, J. F.; McLendon, G. L. Adv. Chem. Ser. 1998, 254, 145-159. Rabanal, F.; Gibney, B. R.; DeGrado, W. F.; Moser, C. C.; Dutton, P. L. Inorg. Chim. Acta 1996, 243, 213.
2. For reviews see: Vullev, V. I.; Jones, G, II. Res. Chem. Interm. In press. Ogawa, M. Y. Mol. Supramol. Photochem. 1999, 4, 113. Mutz, M. W.; Wishart, J. F.; McLendon, G. L. Adv. Chem. Ser. 1998, 254, 145-159. Rabanal, F.; Gibney, B. R.; DeGrado, W. F.; Moser, C. C.; Dutton, P. L. Inorg. Chim. Acta 1996, 243, 213.
3. For reviews see: Vullev, V. I.; Jones, G, II. Res. Chem. Interm. In press. Ogawa, M. Y. Mol. Supramol. Photochem. 1999, 4, 113. Mutz, M. W.; Wishart, J. F.; McLendon, G. L. Adv. Chem. Ser. 1998, 254, 145-159. Rabanal, F.; Gibney, B. R.; DeGrado, W. F.; Moser, C. C.; Dutton, P. L. Inorg. Chim. Acta 1996, 243, 213.
4. For reviews see: Vullev, V. I.; Jones, G, II. Res. Chem. Interm. In press. Ogawa, M. Y. Mol. Supramol. Photochem. 1999, 4, 113. Mutz, M. W.; Wishart, J. F.; McLendon, G. L. Adv. Chem. Ser. 1998, 254, 145-159. Rabanal, F.; Gibney, B. R.; DeGrado, W. F.; Moser, C. C.; Dutton, P. L. Inorg. Chim. Acta 1996, 243, 213.
5. The name TT (i.e., Two Towers) is assigned to series of polypeptides designed to form co-directional helix dimers, e.g., TT1, TT2, etc. The lower-case letter corresponds to the moiety that caps the N-terminus, e.g., "p" for pyrene, "o" for oxopyrene, "b" for butyrate, etc.
6. Fox, M. A.; Galoppini, E. J. Am. Chem. Soc. 1997, 119, 5277. Galoppini, E.; Fox, M. A. J. Am. Chem. Soc. 1996, 118, 2299.
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13. Daugherty, D. L.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 4325.
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15. Jones, G., II.; Vullev, V. I. Org. Lett. 2001, 3, 2457.
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18. 15
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21. 18 was applied as a standard.
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24. Although for TT2o and TT2o± at 337 and 355 nm up to ∼20% of the excitation energy is absorbed by the electron donor, i.e., the carbazole (Cb), we have a reason to believe that the energy (or an electron) is transferred from Cb to the pyrenyl ketone in less than a nanosecond since no carbazole emission or triplet formation has been detected.
25. James, D. R.; Siemiarczuk, A. Rev. Sci. Instrum. 1992, 63, 1710.
26. The emission of OPBA appears to be quenched, probably because of the carboxylate that is 3 σ-bonds away from the chromophore.
27. From emission data it was deduced that in aqueous medium more than ∼85% of the principal chromophore of the polypeptides is in aggregated form and, hence, almost all of the excitation energy is absorbed by aggregated pyrenyl ketone. Therefore, the analysis of the fluorescence quenching is concentrated solely on the red-shifted band of the emission spectra (see Supporting Information for details).
28. Moser, C. C.; Dutton, P. L. Biochim. Biophys. Acta 1992, 1101, 171.
29. Beratan, D. N.; Skourtis, S. S. Curr. Opin. Chem. Biol. 1998, 2, 235.
30. et observed for analogous homo and hetero polypeptide aggregates (Table 1).
31. Jones, G., II.; Vullev, V. I. Photochem. Photobiol. Sci. In press. Vullev, V. I. PhD Dissertation, Boston University, 2001, pp 205-209 and 571-582.
32. Jones, G., II.; Vullev, V. I. Photochem. Photobiol. Sci. In press. Vullev, V. I. PhD Dissertation, Boston University, 2001, pp 205-209 and 571-582.
33. Note that the absorbances of OPy triplet and radical-anion overlap (Figure 3). Hence, the fast component at 500 nm is ascribed to the radical decay, and the slow component to the triplet (Figure 3b and d).
34. This is article No. 13 in the series Photoactive Polypeptides from Boston University.