Development of a new class of photochromic peptides by using diarylethene-based non-natural amino acids

Tetrahedron

Volumn 69, Issue 30, 2013, Pages 6170-6175

  Fujimoto, Kazuhisa ^a   Maruyama, Tatsuya ^b   Okada, Yohei ^b   Itou, Tatsuya ^b   Inouye, Masahiko ^b  

^a KYUSHU SANGYO UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Cyclic peptide; Diarylethene; Non natural amino acid; Photochromic peptide

Indexed keywords

1 (5' BROMO 2' METHYLTHIEN 3' YL) 2 (5' CARBOXY 2' METHYLTHIEN 3' YL)PERFLUOROCYCLOPENTENE; 1 (5' BROMO 2',4' DIMETHYLTHIEN 3' YL) 2 (5' CARBOXY 2' METHYLTHIEN 3' YL)PERFLUOROCYCLOPENTENE; 1 (5' CARBOXY 2' METHYLTHIEN 3' YL) 2 (5' FORMYL 2' METHYLTHIEN 3' YL)PERFLUOROCYCLOPENTENE; 1 (5' CARBOXY 2',4' METHYLTHIEN 3' YL) 2 (5' FORMYL 2',4' METHYLTHIEN 30 YL)PERFLUOROCYCLOPENTENE; AMINO ACID; CYCLOPEPTIDE; DIARYLETHENE; ETHYLENE; PEPTIDE DERIVATIVE; PHOTOCHROMIC PEPTIDE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ISOMERIZATION; PEPTIDE SYNTHESIS; PHOTODEGRADATION; PRIORITY JOURNAL; SOLID PHASE SYNTHESIS; ULTRAVIOLET IRRADIATION;

EID: 84878913977     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.05.044     Document Type: Article

References (34)

1. M. Irie Photochem. Photobiol. Sci. 9 2010 1535 1542
2. M. Irie Proc. Jpn. Acad., Ser. B 86 2010 472 483
3. M. Morimoto, S. Kobatake, and M. Irie Chem. Rec. 4 2004 23 38
4. H. Tian, and S. Yang Chem. Soc. Rev. 33 2004 85 97
5. H. Cahova, and A. Jaeschke Angew. Chem., Int. Ed. 52 2013 1 6
6. S. Barrois, and H.-A. Wagenknecht Beilstein J. Org. Chem. 8 2012 905 914
7. S.-C. Pang, H. Hyun, S. Lee, D. Jang, M.J. Lee, S.H. Kang, and K.-H. Ahn Chem. Commun. 2012 3745 3747
8. W. Tan, J. Zhou, F. Li, T. Yi, and H. Tian Chem. - Asian J. 6 2011 1263 1268
9. X. Piao, Y. Zou, J. Wu, C. Li, and T. Yi Org. Lett. 11 2009 3818 3821
10. A.A. Beharry, and G.A. Woolley Chem. Soc. Rev. 40 2011 4422 4433
11. H. Kashida, X. Liang, and H. Asanuma Curr. Org. Chem. 13 2009 1065 1084
12. C. Renner, and L. Moroder ChemBioChem 7 2006 868 878
13. K. Fujimoto, M. Kajino, I. Sakaguchi, and M. Inouye Chem. - Eur. J. 18 2012 9834 9840
14. D. Mitra, D.R. Banerjee, A.K. Das, and A. Basak Bioorg. Med. Chem. Lett. 20 2010 6831 6835
15. A. Basak, D. Mitra, A.K. Das, D. Mohottalage, and A. Basak Bioorg. Med. Chem. Lett. 20 2010 3977 3981
16. K. Rück-Braun, S. Kempa, B. Priewisch, A. Richter, S. Seedorff, and L. Wallach Synthesis 2009 4256 4267
17. A. Basak, D. Mitra, M. Kar, and K. Biradha Chem. Commun. 2008 3067 3069
18. A. Aemissegger, and D. Hilvert Nat. Protoc. 2 2007 161 167
19. J.L. Seon, K.A. Byeong, and Y.P. Soo Macromolecules 38 2005 6236 6239
20. N. Soh, K. Yoshida, H. Nakajima, K. Nakano, T. Imato, T. Fukaminato, and M. Irie Chem. Commun. 2007 5206 5208
21. M. Irie, K. Sakemura, M. Okinaka, and K. Uchida J. Org. Chem. 60 1995 8305 8309
22. Y. Yokoyama Synth. Org. Chem. Jpn. 49 1991 364 372
23. M. Kajino, K. Fujimoto, and M. Inouye J. Am. Chem. Soc. 133 2011 656 659
24. K. Fujimoto, M. Kajino, and M. Inouye Chem. - Eur. J. 14 2008 857 863
25. K. Fujimoto, H. Kawai, M. Amano, and M. Inouye J. Org. Chem. 73 2008 5123 5126
26. K. Fujimoto, M. Amano, Y. Horibe, and M. Inouye Org. Lett. 8 2006 285 287
27. P.D. Patel, I.A. Mikhailov, K.D. Belfield, and E.A. Masunov Int. J. Quantum Chem. 109 2009 3711 3722
28. A. Somogyi, A.G. Harrison, and B. Paizs J. Am. Soc. Mass Spectrom. 23 2012 2055 2058
29. P.G. Young, J.K. Clegg, M. Bhadbhade, and K.A. Jolliffe Chem. Commun. 2011 463 465
30. S. Kihara, H. Takagi, K. Takechi, and K. Takeda J. Phys. Chem. B 112 2008 7631 7644
31. H. Oike React. Funct. Polym. 67 2007 1157 1167
32. G. Mezo, and F. Hudecz Methods Mol. Biol. 298 2005 63 76
33. Photochromic cyclic peptides including azobenzenes: C. Renner, U. Kusebauch, M. Löeweneck, A.G. Milbradt, and L. Moroder J. Pept. Res. 65 2005 4 14
34. M. Irie, T. Lifka, K. Uchida, S. Kobatake, and Y. Shindo Chem. Commun. 1999 747 750