Fluorescent properties of model chromophores of tyrosine-66 substituted mutants of Aequorea green fluorescent protein (GFP)

Tetrahedron Letters

Volumn 39, Issue 29, 1998, Pages 5239-5242

  Kojima, Satoshi ^c   Ohkawa, Hiroko ^c   Hirano, Takashi ^c   Maki, Shojiro ^c   Niwa, Haruki ^c   Ohashi, Mamoru ^c   Inouye, Satoshi ^a   Tsuji, Frederick I ^b  

^a CHISSO CORPORATION   (Japan)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^c UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

Author keywords

Erlermeyer azlactone synthesis; Fluorescence; Mutation; Proteins

Indexed keywords

AEQUORIN; GREEN FLUORESCENT PROTEIN;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; AUTOFLUORESCENCE; CHROMATOPHORE; GENE MUTATION; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

AEQUOREA;

EID: 0032537670     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01031-4     Document Type: Article

References (33)

1. 1. Johnson, F. H.; Shimomura, O. Methods Enzymol. 1978, 57, 271-291.
2. 2. Inouye, S.; Noguchi, M.; Sakaki, Y.; Takagi, Y.; Miyata, T.; Iwanaga, S.; Miyata, T.; Tsuji, F. I. Proc. Natl. Acad. Sci. USA 1985, 82, 3154-3158.
3. 3. Charbonneau, H.; Walsh, K. A.; McCann, R. O.; Prendergast, F. G.; Cormier, M. J.; Vanaman, T. C. Biochemistry 1985, 24, 6762-6771.
4. 4. Johnson, F. H.; Shimomura, O.; Saiga, Y.; Gershman, L. C.; Reynolds, G. T.; Waters, J. R. J. Cell. Comp. Physiol. 1962, 60, 85-103.
5. 5. Morise, H.; Shimomura, O.; Johnson, F. H.; Winant, J. Biochemistry 1974, 13, 2656-2662.
6. 6. Prendergast, F. G.; Mann, K. G. Biochemistry 1978, 17, 3448-3453.
7. 7. Prasher, D. C.; Eckenrode, V. K.; Ward, W. W.; Prendergast, F. G.; Cormier, M. J. Gene 1992, 111, 229-233.
8. 8. Inouye, S.; Tsuji, F. I. FEBS Lett. 1994, 341, 277-280.
9. 9. Inouye, S.; Tsuji, F. I. FEBS Lett. 1994, 351, 211-214.
10. 10. Shimomura, O. FEBS Lett. 1979, 104, 220-222.
11. 11. Cody, C. W.; Prasher, D. C.; Westler, W. M.; Prendergast, F. G.; Ward, W. W. Biochemistry 1993, 32, 1212-1218.
12. 12. Reid, B. G.; Flynn, G. C. Biochemistry 1997, 36, 6786-6791.
13. 13. Niwa, H.; Inouye, S.; Hirano, T.; Matsuno, T.; Kojima, S.; Kubota, M.; Ohashi, M.; Tsuji, F. I. Proc. Natl. Acad. Sci. USA 1996, 93, 13617-13622.
14. 14. Kojima, S.; Hirano, T.; Niwa, H.; Ohashi, M.; Inouye, S.; Tsuji, F. I. Tetrahedron Lett. 1997, 38, 2875-2878.
15. 15. a) Ormö, M.; Cubitt, A. B.; Kallio, K.; Gross, L. A.; Tsien, R. Y.; Remington, S. J. Science 1996, 273, 1392-1395.
16. b) Yang, F.; Moss, L. G; Phillips, G. N. Nature Biotechnology 1996, 14, 1246-1251.
17. c) Brejc, K.; Sixma, T. K.; Kitts, P. A.; Kain, S. R.; Tsien, R. Y.; Ormö, M.; Remington, S. J. Proc. Natl. Acad. Sci. USA 1997, 94, 2306-2311.
18. 16. a) Chalfie, M.; Tu, Y.; Euskirchen, G.; Ward, W. W.; Prasher, D. C. Science 1994, 263, 802-805.
19. b) Wang, S.; Hazelrigg, T. Nature 1994, 369, 400-403.
20. c) Ehrig, T.; O'Kane, D. J.; Prendergast, F. G. FEBS Lett. 1995, 367, 163-166.
21. d) Delagrave, S.; Hawtin, R. E.; Silva, C. M.; Yang, M. M.; Youvan, D. C. Bio/technology 1995, 13, 151-154.
22. e) Ogawa, H.; Inouye, S.; Tsuji, F.I.; Yasuda, K.; Umesono, K. Proc. Natl. Acad. Sci. USA 1995, 92, 11899-11903.
23. f) Kroll, K. L.; Amaya, E. Development 1996, 122, 3173-3183.
24. 17. Heim, R.; Prasher, D.C.; Tsien, R. Y. Proc. Natl. Acad. Sci. USA 1994, 91, 12501-12504.
25. 18. Cubitt, A.B.; Heim, R.; Adams, S. R.; Boyd, A. E.; Gross, L.A.; Tsien, R. Y. Trends in Biochem. Sci. 1995, 20, 448-455.
26. 14 In this study, we prepared 2 via azulactone 5: Buck, J. S.; Ide, W. S. Org. Synthesis, 1943, Coll.Vol. 2, 55-56.
27. 1H NMR, and high resolution mass spectra were obtained for these compounds.
28. 2O 200.0950.
29. 3O 239.1060.
30. 4O 190.0855.
31. 24. Harhash, A. H.; Kassab, N. A. L.; Elbanani, A. A. A. Indian J. Chem.1971, 9, 789-793.
32. 25. Tiwari, S. S.; Satsangi, R. K. J. Indian Chem. Soc. 1979, 56, 627-632.
33. 26. Under acidic conditions 5 exhibited two comparable fluorescence maxima (357 and 402 nm), whereas the fluorescence maximum at 358 nm was observed under neutral conditions.