Development and photo-responsive peptide bond cleavage reaction of two-photon near-infrared excitation-responsive peptide

Tetrahedron Letters

Volumn 51, Issue 21, 2010, Pages 2868-2871

  Shigenaga, Akira ^a   Yamamoto, Jun ^a   Sumikawa, Yoshitake ^a   Furuta, Toshiaki ^b   Otaka, Akira ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b TOHO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; PEPTIDE;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL BOND; CHEMICAL MODIFICATION; INFRARED RADIATION; LASER; PHOTON; PHOTOREACTIVITY; PROTEIN CLEAVAGE;

EID: 77950926132     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.079     Document Type: Article

References (49)

1. For recent application of UV-induced bond cleavage or conformational change of peptide/protein backbone, see:. Eastwood A.L., Blum A.P., Zacharias N.M., and Dougherty D.A. J. Org. Chem. 74 (2009) 9241-9244
2. Peters F.B., Brock A., Wang J.Y., and Schultz P.G. Chem. Biol. 16 (2009) 148-152
3. Celie P.H.N., Toebes M., Rodenko B., Ovaa H., Perrakis A., and Schumacher T.N.M. J. Am. Chem. Soc. 131 (2009) 12298-12304
4. Vila-Perelló M., Hori Y., Ribó M., and Muir T.W. Angew. Chem., Int. Ed. 47 (2008) 7764-7767
5. Kneissl S., Loveridge E.J., Williams C., Crump M.P., and Allemann R.K. ChemBioChem 9 (2008) 3046-3054
6. Taniguchi A., Skwarczynski M., Sohma Y., Okada T., Ikeda K., Prakash H., Mukai H., Hayashi Y., Kimura T., Hirota S., Matsuzaki K., and Kiso Y. ChemBioChem 9 (2008) 3055-3065
7. Katayama K., Tsukiji S., Furuta T., and Nagamune T. Chem. Commun. (2008) 5399-5401
8. Li H., Hah J.-M., and Lawrence D.S. J. Am. Chem. Soc. 130 (2008) 10474-10475
9. Parker L.L., Kurutz J.W., Kent S.B.H., and Kron S.J. Angew. Chem., Int. Ed. 45 (2006) 6322-6325
10. Renner C., and Moroder L. ChemBioChem 7 (2006) 868-878
11. Sohma Y., and Kiso Y. ChemBioChem 7 (2006) 1549-1557
12. Toebes M., Coccoris M., Bins A., Rodenko B., Gomez R., Nieuwkoop N.J., Kasteele W.v.d., Rimmelzwaan G.F., Haanen J.B.A.G., and Schumacher T.N.M. Nat. Med. 12 (2006) 246-251
13. Pellois J.-P., and Muir T.W. Angew. Chem., Int. Ed. 44 (2005) 5713-5717
14. Dos Santos S., Chandravarkar A., Mandal B., Mimna R., Murat K., Saucede L., Tella P., Tuchscherer G., and Mutter M. J. Am. Chem. Soc. 127 (2005) 11888-11889
15. Endo M., Nakayama K., Kaida Y., and Majima T. Angew. Chem., Int. Ed. 43 (2004) 5643-5645
16. Bosques C.J., and Imperiali B. J. Am. Chem. Soc. 125 (2003) 7530-7531
17. England P.M., Lester H.A., Davidson N., and Dougherty D.A. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 11025-11030
18. McCray J.A. Methods Enzymol. 291 (1998) 175-202 and references cited therein
19. Shigenaga A., Yamamoto J., Hirakawa H., Ogura K., Maeda N., Morishita K., and Otaka A. Tetrahedron Lett. 51 (2010) 2525-2528
20. Shigenaga A., Yamamoto J., Hirakawa H., Yamaguchi K., and Otaka A. Tetrahedron 65 (2009) 2212-2216
21. Shigenaga A., Tsuji D., Nishioka N., Tsuda S., Itoh K., and Otaka A. ChemBioChem 8 (2007) 1929-1931
22. Jung M.E., and Piizzi G. Chem. Rev. 105 (2005) 1735-1766 and references cited therein
23. Milstien S., and Cohen L.A. Proc. Natl. Acad. Sci. U.S.A. 67 (1970) 1143-1147
24. Furuta T. In: Goeldner M., and Gibens R.S. (Eds). Dynamic Studies in Biology: Phototriggers, Photoswitches and Caged Biomolecules (2005), Wiley-VCH, New York 29-54
25. Kawakami T., Cheng H., Hashiro S., Nomura Y., Tsukiji S., Furuta T., and Nagamune T. ChemBioChem 9 (2008) 1583-1586
26. Furuta T., Watanabe T., Tanabe S., Sakyo J., and Matsuba C. Org. Lett. 9 (2007) 4717-4720
27. Goard M., Aakalu G., Fedoryak O.D., Quinonez C., St. Julien J., Poteet S.J., Schuman E.M., and Dore T.M. Chem. Biol. 12 (2005) 685-693
28. Furuta T., Takeuchi H., Isozaki M., Takahashi Y., Kanehara M., Sugimoto M., Watanabe T., Noguchi K., Dore T.M., Kurahashi T., Iwamura M., and Tsien R.Y. ChemBioChem 5 (2004) 1119-1128
29. Ando H., Furuta T., and Okamoto H. Methods Cell Biol. 77 (2004) 159-171
30. Furuta T., and Noguchi K. TrAC, Trends Anal. Chem. 23 (2004) 511-519
31. Suzuki A.Z., Watanabe T., Kawamoto M., Nishiyama K., Yamashita H., Iwamura M., and Furuta T. Org. Lett. 5 (2003) 4867-4870
32. Ando H., Furuta T., Tsien R.Y., and Okamoto H. Nat. Genet. 28 (2001) 317-325
33. Furuta T., Wang S.S.-H., Dantzker J.L., Dore T.M., Bybee W.J., Callaway E.M., Denk W., and Tsien R.Y. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 1193-1200
34. Davis M.J., Kragor C.H., Reddie K.G., Wilson H.C., Zhu Y., and Dore T.M. J. Org. Chem. 74 (2009) 1721-1729
35. Zhu Y., Pavlos C.M., Toscano J.P., and Dore T.M. J. Am. Chem. Soc. 128 (2006) 4267-4276
36. Fedoryak O.D., and Dore T.M. Org. Lett. 4 (2002) 3419-3422
37. Matsuzaki M., Ellis-Davies G.C.R., Nemoto T., Miyashita Y., Iino M., and Kasai H. Nat. Neurosci. 4 (2001) 1086-1092
38. Denk W., Strickler J.H., and Webb W.W. Science 248 (1990) 73-76
39. For recent application of a 4,5-dimethoxy-2-nitrobenzyl group as a 2PE-responsive caging group in a biological study, see:. Neveu P., Aujard I., Benbrahim C., Saux T.L., Allemand J.-F., Vriz S., Bensimon D., and Jullien L. Angew. Chem., Int. Ed. 47 (2008) 3744-3746
40. Dakin K., and Li W.-H. Cell Calcium 42 (2007) 291-301
41. Zhao J., Gover T.D., Muralidharan S., Auston D.A., Weinreich D., and Kao J.P.Y. Biochemistry 45 (2006) 4915-4926**
42. Kantevari S., Hoang C.J., Ogrodnik J., Egger M., Niggli E., and Ellis-Davies G.C.R. ChemBioChem 7 (2006) 174-180
43. Brown E.B., Shear J.B., Adams S.R., Tsien R.Y., and Webb W.W. Biophys. J. 76 (1999) 489-499
44. Patchornik A., Amit B., and Woodward R.B. J. Am. Chem. Soc. 92 (1970) 6333-6335
45. Wilcox M., Viola R.W., Johnson K.W., Billongton A.P., Carpenter B.K., McCray J.A., Guzikowski A.P., and Hess G.P. J. Org. Chem. 55 (1990) 1585-1589
46. Because racemic Fmoc amino acid 4 was used for Fmoc SPPS, diastereomeric mixture of peptide 5 was generated. These diastereomers were separated by HPLC and the peptide eluted earlier was used for subsequent photolysis experiment.
47. A quantum yield of disappearance of Bz-Gly-ODMNB (DMNB: 4,5-dimethoxy-2-nitrobenzyl) in 3:2 acetonitrile/water was reported as 0.08:. Singh A.K., and Khade P.K. Tetrahedron 61 (2005) 10007-10012
48. Aujard I., Benbrahim C., Gouget M., Ruel O., Baudin J.-B., Neveu P., and Jullien L. Chem. Eur. J. 12 (2006) 6865-6879
49. 10,11 However, we think that combination of these two is novel, and the resulting 2PE-responsive peptide bond cleavage system with potential applicability for biological studies is unprecedented.