Thiourea-enhanced flavin photooxidation of benzyl alcohol

Chemistry - A European Journal

Volumn 14, Issue 6, 2008, Pages 1854-1865

  Svoboda, Jiří ^a   Schmaderer, Harald ^a   König, Burkhard ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Flavins; Photooxidation; Redox chemistry; Thiourea

Indexed keywords

ALDEHYDES; ORGANIC COMPOUNDS; THIOUREAS; UREA;

BENZYL ALCOHOL; FLAVINS; REDOX CHEMISTRY; THIOUREA;

PHOTOOXIDATION;

EID: 45249103176     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701319     Document Type: Article

References (112)

1. S. O. Mansoorabadi, C. J. Thibodeaux, H. Liu, J. Org. Chem. 2007, 72, 6329-6342.
2. V. Massey, Biochem. Soc. Trans. 2000, 28, 283-296.
3. Chemistry and Biochemistry of Ftavoenzymes (Ed.: F. Müller), CRC, Boca Raton, 1991.
4. B. J. Fritz, S. Kasai, K. Matsui, Photochem. Photobiol. 1987, 45, 113-117.
5. A. Bowd, P. Byrom, J. B. Hudson, J. H. Turnbull, Photochem. Photobiol. 1968, 8, 1-10.
6. B. König, M. Pelka, H. Zieg, T. Ritter, H. Bouas-Laurent, R. Bonneau, J.-P. Desvergne, J. Am. Chem. Soc. 1999, 121, 1681-1687.
7. B. J. Jordan, G. Cooke, J. F. Garely, M. A. Pollier, N. Kryvokhyzha, A. Bayir, G. Rabani, V. M. Rolello, Chem. Commun. 2007, 1248-1250.
8. J. B. Caroll, B. J. Jordan, H. Xu, B. Erdogan, L. Lee, L. Cheng, C. Tiernan, G. Cooke, V. M. Rotello, Org. Lett. 2005, 7, 2551-2554.
9. M. Gray, A. J. Goodman, J. B. Carroll, K. Bardon, M. Markey, G. Cooke, V. M. Rotello, Org. Lett. 2004, 6, 385-388.
10. S. M. Butterfield, C. M. Goodman, V. M. Rotello, M. L. Waters, Angew. Chem. 2004, 116, 742-745;
11. Angew. Chem. Int. Ed. 2004, 43, 724-727.
12. Y.-M. Legrand, M. Gray, G. Cooke, V. M. Rotello, J. Am. Chem. Soc. 2003, 125, 15789-15795.
13. G. Cooke, Angew. Chem. 2003, 115, 5008-5018;
14. Angew. Chem. Int. Ed. 2003, 42, 4860-4870.
15. F. Guo, B. H. Chang, C. J. Rizzo, Bioorg. Med. Chem. Lett. 2002, 12, 151-154.
16. C. Behrens, M. Ober, T. Carell, Eur. J. Org. Chem. 2002, 3281-3289.
17. B. König, M. Pelka, R. Reichenbach-Klinke, J. Scheller, J. Daub, Eur. J. Org. Chem. 2001, 2297-2303.
18. A. Niemz, V. M. Rotello, Acc. Chem. Res. 1999, 32, 44-52.
19. J. Butenandt, R. Epple, E.-U. Wallenborn, A. P. M. Eker, V. Gramlich, T. Carell, Chem. Eur. J. 2000, 6, 62-72.
20. V. M. Rotello, Curr. Opin. Chem. Biol. 1999, 3, 747-751.
21. R. Deans, V. M. Rolello, J. Org. Chem. 1997, 62, 4528-4529.
22. E. Breinlinger, A. Niemz, V. M. Rotello, J. Am. Chem. Soc. 1995, 117, 5379-5380.
23. H. A. Staab, P. Kirsch, M. F. Zipplies, A. Weinges, C. Krieger, Chem. Ber. 1994, 127, 1653-1665.
24. T. Akiyama, F. Simeno, M. Murakami, F. Yoneda, J. Am. Chem. Soc. 1992, 114, 6613-6620.
25. I. Tabushi, M. Kodera, J. Am. Chem. Soc. 1987, 109, 4734-4735.
26. S. Shinkai, N. Honda, Y. Ishikawa, O. Manabe, J. Am. Chem. Soc. 1985, 107, 6286-6292.
27. M. F. Zipplies, H. A. Staab, Tetrahedron Lett. 1984, 25, 1035-1038.
28. Y. Yano, E. Ohya, J. Chem. Soc. Perkin Trans. 2 1984, 1227-1230.
29. S. Shinkai, T. Yamashila, Y. Kusano, O. Manabe, J. Am. Chem. Soc. 1982, 104, 563-568.
30. G. Blankenhorn, Eur. J. Biochem. 1975, 50, 351-356.
31. N. J. Leonard, R. F. Lambert, J. Org. Chem. 1969, 34, 3240-3248.
32. A. A. Lindén, M. Johansson, N. Hermanns, J.-E. Bäckvall, J. Org. Chem. 2006, 71, 3849-3853.
33. A. A. Lindén, N. Hermanns, S. Ott, L. Kruger, J.-E. Bäckvall, Chem. Eur. J. 2005, 11, 112-119.
34. Y. Imada, H. Iida, S.-I. Murahashi, T. Naota, Angew. Chem. 2005, 117, 1732-1734;
35. Angew. Chem. Int. Ed. 2005, 44, 1704-1706.
36. R. Cibulka, R. Vasold, B. König, Chem. Eur. J. 2004, 10, 6223-6231.
37. O. Wiest, C. B. Harrison, N. J. Saettel, R. Cibulka, M. Sax, B. König, J. Org. Chem. 2004, 69, 8183-8185.
38. Y. Imada, H. Iida, S. Ono, S.-I. Murahashi, J. Am. Chem. Soc. 2003, 125, 2868-2869.
39. M. J. H. Moonen, M. W. Fraaije, I. M. C. M. Rietjens, C. Laane, W. J. H. van Berkel, Adv. Synth. Catal. 2002, 344, 1023-1035.
40. S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474;
41. Angew. Chem. Int. Ed. 2002, 41, 2366-2368.
42. S.-I. Murahashi, T. Oda, Y. Masui, J. Am. Chem. Soc. 1989, 111, 5002-5003.
43. S. Shinkai, Y.-i. Ishikawa, O. Manabe, Chem. Lett. 1982, 11, 809-812.
44. For a recent review on thiourea-based organocatalysts. see: S. J. Connon, Chem. Eur. J. 2006, 12, 5418-5427.
45. For examples of guest binding by thiourea-containing molecules. see: a) C. Roussel, M. Roman, F. Andreoli, A. Del Rio, R. Faure, N. Vanlhuyne, Chirality 2006, 18, 762-771;
46. b) T. Gunnlaugsson, A. P. Davis, J. E. O'Brien, M. Glynn, Org. Biomol. Chem. 2005, 3, 48-56;
47. c) G. V. Oshovsky, W. Verboom, R. H. Fokkens, D. N. Reinhoudl, Chem. Eur. J. 2004, 10, 2739-2748;
48. d) Z.-Y. Zeng, Y.-B. He, J.-L. Wu, L.-H. Wei, X. Liu, L.-Z. Meng, X. Yang, Eur. J. Org. Chem. 2004, 2888-2893;
49. e) U. Boas, A. J. Karlsson, B. F. M. de Waal, E. W. Meijer, J. Org. Chem. 2001, 66, 2136-2145;
50. f) K. H. Lee, X-I. Hong, Tetrahedron Lett. 2000, 41, 6083-6087;
51. g) K. A. Haushalter, J. Lau, J. D. Roberts, J. Am. Chem. Soc. 1996, 118, 8891-8896.
52. For examples of colourimetric sensors based on thiourea-containing molecules, see: a) J. V. Ros-Lis, R. Martínez-Mánez, F. Sancenón, J. Soto, K. Rurack, H. Weisshoff, Eur. J. Org. Chem. 2007, 2449-2458;
53. b) D. A. Jose, D. K. Kumar, B. Ganguly, A. Das, Org. Lett. 2004, 6, 3445-3448.
54. J. Svoboda, B. König, Chem. Rev. 2006, 106, 5413-5430.
55. Oxidations of alcohols to aldehydes are important synthetic transformations, and environmentally more benign processes which use hydrogen peroxide or aerial oxygen as terminal oxidant are desired. See: a) K. Van Aken, L. Strekowski, L. Patiny, Beilstein J. Org. Chem. 2006, 2, 3;
56. b) C. L. Hill, Nature 1999, 401, 436-437;
57. c) P. T. Anastas, J. C. Warner, in Green Chemistry: Theory and Practice, Oxford University Press, Oxford, 1998.
58. 2, see: R. Kuhn, F. Weygand, Chem. Ber. 1935, 68, 1282-1288, and references therein.
59. T. Harayama, Y. Tezuka, T. Taga, F. Yoneda, Tetrahedron Lett. 1984, 25, 4015-4018, and references therein.
60. S. B. Smith, T. C. Bruice, J. Am. Chem. Soc. 1975, 97, 2875-2881.
61. For examples of catalytic hydrogenation or the action of hydrobromic acid in acetic acid, see: a) N. S. Chowdari, C. F. Barbas III, Org. Lett. 2005, 7, 867-870;
62. b) M. Drag, J. Oleksyszyn, Tetrahedron Lett. 2005, 46, 3359-3362;
63. c) K. Senten, P. van der Veken, I. De Meester, A.-M. Lambeir, S. Scharpé, A. Haemers, K. Augustyns, J. Med. Chem. 2004, 47, 2906-2916;
64. d) A. Mucha, M. Pawetczak, J. Hurek, P. Kafarski, Bioorg. Med. Chem. Lett. 2004, 14, 3113-3116;
65. e) A. P. Owens, A. Nadin, A. C. Talbot, E. E. Clarke, T. Harrison, H. D. Lewis, M. Reilly, J. D. J. Wrigley, J. L. Castro, Bioorg. Med. Chem. Lett. 2003, 13, 4143-4145.
66. P. G. M. Wuts, T. W. Green, in Green's Protective Groups in Organic Synthesis, Wiley, Hoboken, 2006.
67. Modification of a procedure of C. Vergne, M. Bois-Choussy, R. Beugelmans, J. Zhu. Tetrahedron: Asymmetry 1997, 8, 391-398.
68. J. L. Jiménez Blanco, P. Bootello, J. M. Benito, C. Ortiz Mellet, J. M. García Fernandez, J. Org. Chem. 2006, 71, 5136-5143.
69. For the photocatalytic oxidation of 4-methoxybenzyl alcohol to the aldehyde using titanium dioxide, see: G. Palmisano, S. Yurdakal, V. Augugliaro, V. Loddo, L. Palmisano, Adv. Synth. Catal. 2007, 349, 964-970.
70. V. Massey, J. Biol. Chem. 1994, 269, 22459-22462.
71. K. C. Jones, D. P. Ballou, J. Biol. Chem 1986, 261, 2553-2559.
72. To exclude any kinetic deuterium isotope effect on the course of the reaction, analogous experiments were performed in undeuterated solvents and analysed by HPLC, which gave identical results.
73. N. A. Stephenson, A. T. Bell. Anal. Bioanal. Chem. 2005, 381, 1289-1293.
74. In the absence of oxygen, conversion of up to 10% would be still observed, even if the cycle did not proceed, because the flavin is initially in the active oxidised form.
75. F. Y.-H. Wu, R. E. MacKenzie, D. B. McCormick, Biochemistry 1970, 9, 2219-2224.
76. K.-Y. Yang, R. P. Swenson, Biochemistry 2001, 46, 2289-2297.
77. M. Ghanem, G. Gadda, Biochemistry 2006, 45, 3437-3447.
78. R. Singh, Geetanjali, C. R. Babu, Chem. Biodiversity 2005, 2, 429-446.
79. S. Watanabe, N. Kosaka, S.-i. Kondo, Y. Yano, Bull. Chem. Soc. Jpn. 2004, 77, 569-574.
80. Y. Yano, Antioxid. Redox Signaling 2001, 3, 899-909.
81. T. D. Carson, S.-W. Tarn-Chang, H. E. Beck, Antioxid. Redox Signaling 2001, 3, 731-736.
82. Y. Yin, N. S. Sampson, A. Vrielink, P. I. Lario, Biochemistry 2001, 40, 13779-13787.
83. F. G. Bordwell, Acc. Chem. Res 1988, 21, 456-463.
84. W. N. Olmstead, Z. Margolin, F. G. Bordwell, J. Org. Chem. 1980, 45, 3295-3299.
85. D. Rehm, A. Weller, Ber. Dtsch. Chem. Ges 1969, 73, 834-839.
86. F. Scandola, V. Balzani, G. B. Schuster, J. Am. Chem. Soc. 1981, 103, 2519-2523.
87. S. V. Torti, H. Akimoto, K. Lin, M. E. Billingham, F. M. Torti, J. Mol. Cell. Cardiol. 1998, 30, 1173-1180.
88. J. K. Grady, Y. Chen, N. D. Chasteen, D. C. Harris, J. Biol. Chem. 1989, 264, 20224-20229.
89. W.-X. Athena Quo, D. M. Ziegler, Anal. Biochem. 1991, 198, 143-148.
90. The thiourea-isothiourea tautomerisation is induced by light. See: a) A. Macijewski, R. P. Steer, A. Mickiewicz, Chem. Rev. 1993, 93, 67-98;
91. b) L. Lapinski, H. Rostkowska, A. Khvorostov, M. J. Nowak, Phys. Chem. Chem. Phys. 2003, 5, 1524-1529;
92. c) H. Rostkowska, L. Lapinski, A. Khvorostov, M. J. Nowak, J. Phys. Chem. A 2003, 107, 6373-6380.
93. G. S. Misra, U. D. N. Bajpai, J. Trekoval, Rev. Macromol. Chem. Phys. 1984, C24, 335-353.
94. A. Claiborne, H. Miller, D. Parsonage, R. P. Ross, FASEB J. 1993, 7, 1483-1490.
95. A. Claiborne, R. P. Ross, D. Parsonage, Trends Biochem. Sci. 1992, 17, 183-186.
96. J. S. O'Donnel, A. L. Schwan, J. Sulfur Chem. 2004, 25, 183-211.
97. F. A. Davis, L. A. Jenkins, R. L. Billmers, J. Org. Chem. 1986, 51, 1033-1040.
98. F. A. Davis, R. L. Billmers, J. Am. Chem. Soc. 1981, 103, 7016-7018.
99. W. S. Allison, Acc. Chem. Res 1976, 9, 293-299.
100. R. Epple, E.-U. Wallenborn, T. Carell, J. Am. Chem. Soc. 1997, 119, 7440-7451.
101. a) A. Gheorghe, Dissertation, Universität Regensburg, 2006;
102. b) H. Trabelsi, F. Szönyi, N. Michelangeli, A. Cambon, J. Fluorine Chem. 1994, 69, 115-117;
103. c) F. Szönyi, F. Guennouni, A. Cambon, J. Fluorine Chem. 1991, 55, 85-92.
104. N. Sakai, D. Gerard, S. Malile, J. Am. Chem. Soc. 2001, 123, 2517-2524.
105. Norel-507 HP tubes, fully transparent to 440 nm light, were used.
106. S. L. Murov, Handbook of Photochemistry. Marcel Dekker, New York, 1973.
107. S. N. Sawhney, D. W. Boykin, J. Heterocycl, Chem. 1979, 16, 397-400.
108. M. Nicola, G. Gaviraghi, M. Pinza, G. Pifferi, J. Heterocycl, Chem. 1981, 18, 825-829.
109. Z.-L. Zhou, S. M. Kher, S. X. Cai, E. R. Whitlemore, S. A. Espitia, J. E. Hawkinson, M. Tran, R. M. Woodward, E. Weber, J. F. Keana, Bioorg. Med. Chem. 2003, 11, 1769-1780.
110. M. Rangarajan, J. S. Kim, S.-P. Sim, A. Liu, L. F. Liu, E. J. La Voie, Bioorg. Med. Chem. 2000, 8, 2591-2600.
111. For a detailed discussion on flavin fragmentation in EI-MS measurements, see: P. Brown, C. L. Hornbeck, J. R. Cronin, Org. Mass Spectrom. 1972, 6, 1383-1399.
112. C. G. van Schagen, F. Müller. Helv. Chim. Acta 1978, 61, 3139-3142.