Reversible photoregulation of helical structures in short peptides under indoor lighting/dark conditions

Organic Letters

Volumn 8, Issue 2, 2006, Pages 285-287

  Fujimoto, Kazuhisa ^a   Amano, Miwo ^a   Horibe, Yohei ^a   Inouye, Masahiko ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS LINKING REAGENT; PEPTIDE;

ARTICLE; CHEMISTRY; PHOTOCHEMISTRY; PROTEIN SECONDARY STRUCTURE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CROSS-LINKING REAGENTS; PEPTIDES; PHOTOCHEMISTRY; PROTEIN STRUCTURE, SECONDARY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 31544482648     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0526524     Document Type: Article

References (25)

1. Sewald, N., Jakubke, H.-D., Eds.; Peptides: Chemistry and Biology; Wiley-VCH: Weinheim, 2002; Chapter 3.
2. Recent papers: (a) Futaki, S.; Kiwada, T.; Sugiura, Y. J. Am. Chem. Soc. 2004, 126, 15762-15769.
3. (b) Lin, J. C.; Barua, B.; Andersen, N. H. J. Am. Chem. Soc. 2004, 126, 13679-13684.
4. (c) Verma, A.; Nakade, H.; Simard, J. M.; Rotello, V. M. J. Am. Chem. Soc. 2004, 126, 10806-10807.
5. (d) Cline, D. J.; Thorpe, C.; Schneider, J. P. J. Am. Chem. Soc. 2003, 125, 2923-2929.
6. (e) Neidigh, J. W.; Fesinmeyer, R. M.; Andersen, N. H. Nat. Struct. Biol. 2002, 9, 425-430.
7. (f) Schafmeister, C. E.; Po, J.; Verdine, G. L. J. Am. Chem. Soc. 2000, 122, 5891-5892.
8. Fujimoto, K.; Oimoto, N.; Katsuno, K.; Inouye, M. Chem. Commun. 2004, 1280-1281.
9. For the photoregulation of helical structures on polypeptides by multiple modifications with photochromic compounds as a pendant style, see: (a) Pieroni, O.; Fissi, A.; Angelini, N.; Lenci, F. Acc. Chem. Res. 2001, 34, 9-17.
10. (b) Inouye, M. In Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Plenum: New York, 1999; Vol. 2, pp 393-402.
11. (c) Goodman, M.; Kossoy, A. J. Am. Chem. Soc. 1966, 88, 5010-5015.
12. (a) Woolley, G. A. Acc. Chem. Res. 2005, 38, 486-493.
13. (b) Zhang, Z.; Burns, D. C.; Kumita, J. R.; Smart, O. S.; Woolley, G. A. Bioconjugate Chem. 2003, 14, 824-829.
14. (c) Kumita, J. R.; Flint, D. G.; Smart, O. S.; Woolley, G. A. Protein Eng. 2002, 15, 561-569.
15. (d) Flint, D. G.; Kumita, J. R.; Smart, O. S.; Woolley, G. A. Chem. Biol. 2002, 9, 391-397.
16. (e) Kumita, J. R.; Smart, O. S.; Woolley, G. A. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 3803-3808.
17. (a) Bertlson, R. C. In Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Plenum: New York, 1999: Vol. 1, pp 11-83.
18. (b) Inouye, M. Coord. Chem. Rev. 1996, 148, 265-283.
19. (c) Guglielmetti, R. In Photochromism Molecules and Systems; Dürr, H., Bouas-Laurent, H., Eds.: Elsevier: Amsterdam, 1990; Chapter 8.
20. Huang, C.-H.; He, S.; DeGrado, W. F.; McCafferty, D. G.; Gai, F. J. Am. Chem. Soc. 2002, 124, 12674-12675 and references therein.
21. Li, X.; Wang, Y.; Matsuura, T.; Meng, J. Heterocycles 1999, 57, 2639-2651.
22. Inouye, M.; Noguchi, Y.; Isagawa, K. Angew. Chem., Int. Ed. Engl. 1994, 35, 1163-1166.
23. Which is which is not determined.
24. For the conversion of ellipticity to % helix, see ref 2f. During the photochromic process of the cross-linked peptides, the CD spectral changes were accompanied by an isodichroic point at 203 nm, and this implied that the chromophoric spiropyran and merocyanine portions do not interfere with the CD spectra.
25. 1H NMR spectrum under the same dark conditions, and (3) the coefficient of the control compound was assumed to be the same as that of the cross-linked peptide.