Design and concise synthesis of a novel type of green fluorescent protein chromophore analogue

Organic Letters

Volumn 14, Issue 17, 2012, Pages 4406-4409

  Ikejiri, Masahiro ^a   Tsuchino, Moe ^a   Chihara, Yoshiko ^a   Yamaguchi, Takao ^b   Imanishi, Takeshi ^b   Obika, Satoshi ^b   Miyashita, Kazuyuki ^a  

^a OSAKA OHTANI UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; DNA; FLUORESCENT DYE; GREEN FLUORESCENT PROTEIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; SOLUTION AND SOLUBILITY; SYNTHESIS;

AZIRIDINES; DNA; FLUORESCENCE; FLUORESCENT DYES; GREEN FLUORESCENT PROTEINS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SOLUTIONS;

EID: 84866011187     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301901e     Document Type: Article

References (24)

1. For a recent review, see: Kobayashi, H.; Ogawa, M.; Alford, R.; Choyke, P. L.; Urano, Y. Chem. Rev. 2010, 110, 2620-2640
2. GFP review: Zimmer, M. Chem. Rev. 2002, 102, 759-781
3. He, X.; Bell, A. F.; Tonge, P. J. Org. Lett. 2002, 4, 1523-1526
4. Petersen, M. Å.; Riber, P.; Andersen, L. H.; Nielsen, M. B. Synthesis 2007, 3635-3638
5. Lincke, K.; Sølling, T.; Andersen, L. H.; Klærke, B.; Rahbek, D. B.; Rajput, J.; Oehlenschlæger, C. B.; Petersen, M. Å.; Nielsen, M. B. Chem. Commun. 2010, 46, 734-736
6. Kartritzky, A. R.; Yoshioka-Tarver, M.; El-Gendy, B. M.; Hall, C. Tetrahedron Lett. 2011, 52, 2224-2227
7. Tolbert, L. M.; Baldridge, A.; Kowalik, J.; Solntsev, K. M. Acc. Chem. Res. 2012, 45, 171-181 and references therein
8. Baranov, M. A.; Lukyanov, K. A.; Borissova, A. O.; Shamir, J.; Kosenkov, D.; Slipchenko, L. V.; Tolbert, L. M.; Yampolsky, I. V.; Solntsev, K. M. J. Am. Chem. Soc. 2012, 134, 6025-6032
9. Baldridge, A.; Samanta, S. R.; Jayaraj, N.; Ramamurthy, V.; Tolbert, L. M. J. Am. Chem. Soc. 2010, 132, 1498-1499
10. Cacciarini, M.; Nielsen, M. B.; de Castro, E. M.; Marinescu, L.; Bols, M. Tetrahedron Lett 2012, 53, 973-976
11. Wu, L.; Burgess, K. J. Am. Chem. Soc. 2008, 130, 4089-4096
12. Kojima, S.; Ohkawa, H.; Hirano, T.; Maki, S.; Niwa, H.; Ohashi, M.; Inouye, S.; Tsuji, F. I. Tetrahedron Lett. 1998, 39, 5239-5242
13. Recently, Jaffrey and co-workers reported fluorescent RNA aptamers that bind modified GFP chromophores: Paige, J. S.; Wu, K. Y.; Jaffrey, S. R. Science 2011, 333, 642-646
14. Niwa, H.; Inouye, S.; Hirano, T.; Matsuno, T.; Kojima, S.; Kubota, M.; Ohashi, M.; Tsuji, F. I. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 13617-13622
15. Voliani, V.; Bizzarri, R.; Nifosì, R.; Abbruzzetti, S.; Grandi, E.; Viappiani, C.; Beltram, F. J. Phys. Chem. B 2008, 112, 10714-10722
16. Dong, J.; Abulwerdi, F.; Baldridge, A.; Kowalik, J.; Solntsev, K. M.; Tolbert, L. M. J. Am. Chem. Soc. 2008, 130, 14096-14098 and references therein
17. Vicario, J.; Walko, M.; Meetsma, A.; Feringa, B. L. J. Am. Chem. Soc. 2006, 128, 5127-5135
18. Baldridge, A.; Kowalik, J.; Tolbert, L. M. Synthesis 2010, 2424-2436
19. Rao, M. N.; Holkar, A. G.; Ayyangar, N. R. Tetrahedron Lett. 1989, 30, 4717-4720
20. Dong, J.; Solntsev, K. M.; Tolbert, L. M. J. Am. Chem. Soc. 2009, 131, 662-670
21. Chuang, W. T.; Hsieh, C. C.; Lai, C. H.; Lai, C. H.; Shih, C. W.; Chen, K. Y.; Hung, W. Y.; Hsu, Y. H.; Chou, P. T. J. Org. Chem. 2011, 76, 8189-8202
22. Quillin, M. L.; Anstrom, D. M.; Shu, X.; O'Leary, S.; Kallio, K.; Chudakov, D. M.; Remington, S. J. Biochemistry 2005, 44, 5774-5787
23. Occhiato, E. G.; Ferrali, A.; Menchi, G.; Guarna, A.; Danza, G.; Comerci, A.; Mancina, R.; Serio, M.; Garotta, G.; Cavalli, A.; De Vivo, M.; Recanatini, M. J. Med. Chem. 2004, 47, 3546-3560
24. Olmsted, J., III; Kearns, D. R. Biochemistry 1977, 16, 3647-3654