A synthetic GFP-like chromophore undergoes base-catalyzed autoxidation into acylimine red form

Journal of Organic Chemistry

Volumn 76, Issue 8, 2011, Pages 2782-2791

  Ivashkin, Pavel E ^a   Lukyanov, Konstantin A ^a   Lukyanov, Sergey ^a   Yampolsky, Ilia V ^a  

^a SHEMYAKIN OVCHINNIKOV INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

AEROBIC CONDITION; AMINO ACID RESIDUES; BASIC CONDITIONS; CHEMICAL NATURE; CHROMOPHORE FORMATION; ELECTRON OXIDATION; EXPERIMENTAL BIOLOGY; FLUORESCENT PROTEIN; KEY FACTORS; MODEL COMPOUND; RED-SHIFTED;

AMINO ACIDS; BIOMIMETICS; MOLECULAR OXYGEN; OXIDATION;

CHROMOPHORES;

AMINO ACID; GREEN FLUORESCENT PROTEIN; IMIDE; N [1 [4 (4 HYDROXYBENZYLIDENE) 1 METHYL 5 OXO 4,5 DIHYDRO 1H IMIDAZOL 2 YL] 2 PHENYLETHYL]ACETAMIDE; N [1 [4 (4 HYDROXYBENZYLIDENE) 1 METHYL 5 OXO 4,5 DIHYDRO 1H IMIDAZOL 2 YL] 2,2 DIMETHYLPROPYL]ACETAMIDE; N [[4 (4 HYDROXYBENZYLIDENE) 1 METHYL 5 OXO 4,5 DIHYDRO 1H IMIDAZOL 2 YL]METHYL]ACETAMIDE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; AUTOOXIDATION; BIOMIMETICS; CATALYST; CYCLIZATION; ELIMINATION REACTION; SYNTHESIS;

ALKALIES; AMINO ACID SUBSTITUTION; CATALYSIS; CYCLIZATION; GREEN FLUORESCENT PROTEINS; IMINES; LUMINESCENT PROTEINS; MOLECULAR MIMICRY; MOLECULAR PROBES; OXIDATION-REDUCTION; OXYGEN;

EID: 79953884032     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200150b     Document Type: Article

References (32)

1. Chudakov, D. M.; Lukyanov, S.; Lukyanov, K. A. Trends Biotechnol. 2005, 23, 605
2. Pakhomov, A. A.; Martynov, V. I. Chem. Biol. 2008, 15, 755
3. Gross, L. A.; Baird, G. S.; Hoffman, R. C.; Baldridge, K. K.; Tsien, R. Y. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 11990
4. Yarbrough, D.; Wachter, R. M.; Kallio, K.; Matz, M. V.; Remington, S. J. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 462
5. Quillin, M. L.; Anstrom, D. M.; Shu, X.; O'Leary, S.; Kallio, K.; Chudakov, D. M.; Remington, S. J. Biochemistry 2005, 44, 5774
6. Yampolsky, I. V.; Remington, S. J.; Martynov, V. I.; Potapov, V. K.; Lukyanov, S.; Lukyanov, K. A. Biochemistry 2005, 44, 5788
7. Subach, O. M.; Malashkevich, V. N.; Zencheck, W. D.; Morozova, K. S.; Piatkevich, K. D.; Almo, S. C.; Verkhusha, V. V. Chem. Biol. 2010, 17, 333
8. Strack, R. L.; Strongin, D. E.; Mets, L.; Glick, B. S.; Keenan, R. J. J. Am. Chem. Soc. 2010, 132, 8496
9. Pakhomov, A. A.; Martynov, V. I. Biochemistry 2007, 46, 11528
10. Pakhomov, A.; Tretyakova, Y.; Martynov, V. Russ. J. Bioorg. Chem. 2010, 36, 109
11. Kojima, S.; Ohkawa, H.; Hirano, T.; Maki, S.; Niwa, H.; Ohashi, M.; Inouye, S.; Tsuji, F. I. Tetrahedron Lett. 1998, 39, 5239
12. Yampolsky, I. V.; Kislukhin, A. A.; Amatov, T. T.; Shcherbo, D.; Potapov, V. K.; Lukyanov, S.; Lukyanov, K. A. Bioorg. Chem. 2008, 36, 96
13. Bulina, M.; Chudakov, D.; Mudrik, N.; Lukyanov, K. BMC Biochem. 2002, 3, 7
14. Ivashkin, P.; Yampolsky, I.; Lukyanov, K. Russ. J. Bioorg. Chem. 2009, 35, 652
15. Devasia, G. M. Tetrahedron Lett. 1976, 17, 571
16. Ekeley, J. B.; Ronzio, A. R. J. Am. Chem. Soc. 1935, 57, 1353
17. Kidwai, A. R.; Devasia, G. M. J. Org. Chem. 1962, 27, 4527
18. Wu, L.; Burgess, K. J. Am. Chem. Soc. 2008, 130, 4089
19. Oumouch, S.; Bourotte, M.; Schmitt, M.; Bourguignon, J.-J. Synthesis 2005, 25
20. Boyd, V. L.; Bozzini, M.; Guga, P. J.; DeFranco, R. J.; Yuan, P.-M.; Loudon, G. M.; Nguyen, D. J. Org. Chem. 1995, 60, 2581
21. Shin, C.-g.; Yonezawa, Y.; Obara, T.; Nishio, H. Bull. Chem. Soc. Jpn. 1988, 61, 885
22. Bolhofer, W. A. J. Am. Chem. Soc. 1954, 76, 1322
23. Shigematsu, N.; Kayakiri, N.; Okada, S.; Tanaka, H. Bull. Chem. Soc. Jpn. 1997, 45, 236
24. Yampolsky, I. V.; Balashova, T. A.; Lukyanov, K. A. Biochemistry 2009, 48, 8077
25. Pletneva, N.; Pletnev, S.; Tikhonova, T.; Popov, V.; Martynov, V.; Pletnev, V. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2006, 62, 527
26. Pletneva, N.; Pletnev, V.; Tikhonova, T.; Pakhomov, A. A.; Popov, V.; Martynov, V. I.; Wlodawer, A.; Dauter, Z.; Pletnev, S. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2007, 63, 1082
27. Remington, S. J.; Wachter, R. M.; Yarbrough, D. K.; Branchaud, B.; Anderson, D. C.; Kallio, K.; Lukyanov, K. A. Biochemistry 2005, 44, 202
28. Mizuno, H.; Mal, T. K.; Tong, K. I.; Ando, R.; Furuta, T.; Ikura, M.; Miyawaki, A. Mol. Cell 2003, 12, 1051
29. Shagin, D. A.; Barsova, E. V.; Yanushevich, Y. G.; Fradkov, A. F.; Lukyanov, K. A.; Labas, Y. A.; Semenova, T. N.; Ugalde, J. A.; Meyers, A.; Nunez, J. M.; Widder, E. A.; Lukyanov, S. A.; Matz, M. V. Mol. Biol. Evol. 2004, 21, 841
30. Bomati, E. K.; Manning, G.; Deheyn, D. D. BMC Evol Biol. 2009, 9, 77
31. Jaeger, D. A.; Broadhurst, M. D.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 717
32. Boger, D. L.; Zhou, J.; Borzilleri, R. M.; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 2054