Why is firefly oxyluciferin a notoriously labile substance?

Angewandte Chemie - International Edition

Volumn 53, Issue 3, 2014, Pages 847-850

  Maltsev, Oleg V ^a   Nath, Naba K ^b   Naumov, Panče ^b   Hintermann, Lukas ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b NEW YORK UNIVERSITY ABU DHABI   (United Arab Emirates)

Author keywords

bioorganic chemistry; heterocycles; luminescence; natural products; structure elucidation

Indexed keywords

BIOCHEMISTRY; BIOLUMINESCENCE; CHEMICAL ANALYSIS; FLUORESCENCE; LUMINESCENCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORESCENCE;

BIOLUMINESCENT SYSTEMS; BIOORGANIC CHEMISTRY; GREEN FLUORESCENCE; HETEROCYCLES; MANNICH REACTIONS; MANNICH-TYPE REACTIONS; NATURAL PRODUCTS; STRUCTURE ELUCIDATION;

X RAY CRYSTALLOGRAPHY;

INDOLE DERIVATIVE; KETONE; MANNICH BASE; OXYLUCIFERIN; PYRAZINE DERIVATIVE;

ANIMAL; ARTICLE; BIOORGANIC CHEMISTRY; CHEMISTRY; CONFORMATION; DIMERIZATION; FIREFLY; HETEROCYCLES; LUMINESCENCE; METABOLISM; NATURAL PRODUCTS; STRUCTURE ELUCIDATION; TIME; X RAY CRYSTALLOGRAPHY;

BIOORGANIC CHEMISTRY; HETEROCYCLES; LUMINESCENCE; NATURAL PRODUCTS; STRUCTURE ELUCIDATION;

ANIMALS; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; FIREFLIES; INDOLES; KETONES; MANNICH BASES; MOLECULAR CONFORMATION; PYRAZINES; TIME FACTORS;

EID: 84891837896     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201307972     Document Type: Article

References (44)

1. Recent reviews: a) T. Ozawa, H. Yoshimura, S. B. Kim, Anal. Chem. 2013, 85, 590;
2. b) J. Li, L. Chen, L. Du, M. Li, Chem. Soc. Rev. 2013, 42, 662;
3. c) M. Kelkar, A. De, Curr. Opin. Pharmacol. 2012, 12, 592;
4. d) M. Keyaerts, V. Caveliers, T. Lahoutte, Trends Mol. Med. 2012, 18, 164;
5. e) A. Roda, M. Guardigli, Anal. Bioanal. Chem. 2012, 402, 69.
6. O. Shimomura, Bioluminescence: Chemical Principles and Methods, rev. ed., World Scientific, Singapore, 2012.
7. The term "labile" is used in the sense of "reactive", irrespective of thermodynamic stability. Oxyluciferin is a good example for a labile species (depending on conditions) that is not fundamentally unstable. See: IUPAC, Compendium of Chemical Terminology (the "Gold Book"), 2nd ed. (Eds.: A. D. McNaught, A. Wilkinson), Blackwell Scientific Publications, Oxford, 1997.
8. E. H.White, D. F. Roswell, Photochem. Photobiol. 1991, 53, 131.
9. E. H. White, E. Rapaport, H. H. Seliger, T. A. Hopkins, Bioorg. Chem. 1971, 1, 92.
10. a) N. Suzuki, M. Sato, K. Okada, T. Goto, Tetrahedron 1972, 28, 4065;
11. b) N. Suzuki, M. Sato, K. Nishikawa, T. Goto, Tetrahedron Lett. 1969, 10, 4683.
12. N. Suzuki, T. Goto, Tetrahedron 1972, 28, 4075.
13. B. Bitler,W. D. McElroy, Arch. Biochem. Biophys. 1957, 72, 358.
14. N. Suzuki, T. Goto, Tetrahedron Lett. 1971, 12, 2021.
15. J. C. G. Esteves da Silva, J. M. C. S. Magalhaes, R. Fontes, Tetrahedron Lett. 2001, 42, 8173.
16. N. Suzuki, T. Goto, Agric. Biol. Chem. 1972, 36, 2213.
17. P. Naumov, Y. Ozawa, K. Ohkubo, S. Fukuzumi, J. Am. Chem. Soc. 2009, 131, 11590.
18. O. A. Gandelman, L. Y. Brovko, N. N. Ugarova, A. Y. Chikishev, A. P. Shkurimov, J. Photochem. Photobiol. B 1993, 19, 187.
19. a) K. Støchkel, C. N. Hansen, J. Houmøller, L. M. Nielsen, K. Anggara, M. Linares, P. Norman, F. Nogueira, O. V. Maltsev, L. Hintermann, S. B. Nielsen, P. Naumov, B. F. Milne, J. Am. Chem. Soc. 2013, 135, 6485;
20. b) K. M. Solntsev, S. P. Laptenok, P. Naumov, J. Am. Chem. Soc. 2012, 134, 16452;
21. c) Y. Erez, I. Presiado, R. Gepshtein, L. Pinto da Silva, J. C. G. Esteves da Silva, D. Huppert, J. Phys. Chem. A 2012, 116, 7452;
22. d) P. Naumov,M. Kochunnoonny, J. Am. Chem. Soc. 2010, 132, 11566;
23. e) C. Ribeiro, J. C. G. Esteves da Silva, Photochem. Photobiol. Sci. 2008, 7, 1085.
24. a) T. Hirano, H. Nagai, T. Matsuhashi, Y. Hasumi, S. Iwano, K. Ito, S. Maki, H. Niwa, V. R. Viviani, Photochem. Photobiol. Sci. 2012, 11, 1281;
25. b) T. N. Vlasova, O. V. Leontieva, N. N. Ugarova, Biochemistry 2006, 71, 555;
26. c) O. V. Leontieva, T. N. Vlasova, N. N. Ugarova, Biochemistry 2006, 71, 51.
27. Recent examples: a) I. Navizet, D. Roca-Sanjuan, L. Yue, Y. J. Liu, N. Ferre, R. Lindh, Photochem. Photobiol. 2013, 89, 319;
28. b) V. R. Viviani, D. T. Amaral, D. R. Neves, A. Simoes, F. G. C. Arnoldi, Biochemistry 2013, 52, 19;
29. c) L. Pinto da Silva, J. C. G. Esteves da Silva, Int. J. Quantum Chem. 2013, 113, 45;
30. d) M. Anselmi, S. Marocchi, M. Aschi, A. Amadei, Chem. Phys. 2012, 392, 205;
31. e) Z. S. Li, C. G. Min, A. M. Ren, L. Y. Zou, Z. Xu, J. Photochem. Photobiol. A 2012, 243, 7.
32. a) L.W. Chung, S. Hayashi, M. Lundberg, T. Nakatsu, H. Kato, K. Morokuma, J. Am. Chem. Soc. 2008, 130, 12880;
33. b) T. Nakatsu, S. Ichiyama, J. Hiratake, A. Saldanha, N. Kobashi, K. Sakata, H. Kato, Nature 2006, 440, 372;
34. c) B. R. Branchini, M. H. Murtiashaw, R. A. Magyar, N. C. Porter, M. C. Ruggiero, J. G. Stroh, J. Am. Chem. Soc. 2002, 124, 2112.
35. M. Rebarz, B.-M. Kukovec, O. V. Maltsev, C. Ruckebusch, L. Hintermann, P. Naumov, M. Sliwa, Chem. Sci. 2013, 4, 3803.
36. a) K. A. Jensen, I. Crossland, Acta Chem. Scand. 1963, 17, 144;
37. b) S. Gronowitz, B. Mathiasson, R. Dahlbom, B. Holmberg, K. A. Jensen, Acta Chem. Scand. 1965, 19, 1215.
38. a) K. Gomi, N. Kajiyama, J. Biol. Chem. 2001, 276, 36508;
39. b) K. Okada, H. Iio, I. Kubota, T. Goto, Tetrahedron Lett. 1974, 15, 2771.
40. G. C. Barrett, Tetrahedron 1980, 36, 2023.
41. The lability is restricted to derivatives devoid of substituents at C-5, cf.: E. Tuscher, R. Beckert, J. Fabian, A. Assumpo, H. Gçrls, Tetrahedron Lett. 2011, 52, 2292.
42. B. Holmberg, Ark. Kemi Mineral. Geol. 1945, 20A, No. 1.
43. A compound with this structure has been reported, without noting its identity to Holmbergs thiazolone: I. E. Kopta, Tetrahedron Lett. 1988, 29, 3765.
44. CCDC-952719 (13) and 952720 (14) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.