Recent Developments in Flavin-based Catalysis

ChemCatChem

Volumn 5, Issue 2, 2013, Pages 403-415

  deGonzalo, Gonzalo ^a   Fraaije, Marco W ^b  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

Cofactor engineering; Flavins; Hydrogenation; Organocatalysis; Photooxidation

Indexed keywords

EID: 84873152061     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201200466     Document Type: Short Survey

References (135)

1. P. Karrer, K. Schöpp, F. Benz, Helv. Chim. Acta 1935, 18, 426-429;
2. R. Kuhn, K. Reinemund, F. Weygand, Helv. Chim. Acta 1934, 17, 1460-1463;
3. A. W. Blyth, J. Chem. Soc. 1879, 35, 530-539.
4. V. Joosten, W. J. vanBerkel, Curr. Opin. Chem. Biol. 2007, 11, 195-202;
5. S. Bornemann, Nat. Prod. Rep. 2002, 19, 761-772;
6. R. Miura, Chem. Rec. 2001, 1, 183-94;
7. M. W. Fraaije, A. Mattevi, Trends Biochem. Sci. 2000, 25, 126-132.
8. H. Liu, S. Matsuda, K. Hashimoto, S. Nakanishi, ChemSusChem 2012, 5, 1054-1058.
9. E. Ott, J. Stolz, M. Lehmann, M. Mack, RNA Biol. 2009, 6, 276-280.
10. C. Walsh, Acc. Chem. Res. 1986, 19, 216-221.
11. A. F. Glas, M. J. Maul, M. Cryle, T. R. Barends, S. Schneider, E. Kaya, I. Schlichting, T. Carell, Proc. Natl. Acad. Sci. USA 2009, 106, 11540-11545.
12. P. Chaiyen, M.W. Fraaije, A. Mattevi, Trends Biochem. Sci. 2012, DOI:;
13. D. E. TorresPazmiño, M. Winkler, A. Glieder, M. W. Fraaije, J. Biotechnol. 2010, 146, 9-24;
14. V. B. Urlacher, R. D. Schmid, Curr. Opin. Chem. Biol. 2006, 10, 156-161;
15. W. J. H. vanBerkel, N. M. Kamerbeek, M. W. Fraaije, J. Biotechnol. 2006, 124, 670-689.
16. J. Piera, J.-E. Bäckvall, Angew. Chem. 2008, 120, 3558-3576; Angew. Chem. Int. Ed. 2008, 47, 3506-3523;
17. F. G. Gelalcha, Chem. Rev. 2007, 107, 3338-3361;
18. Y. Imada, T. Naota, Chem. Rec. 2007, 7, 354-361.
19. T. C. Bruice, Acc. Chem. Res. 1980, 13, 256-262;
20. C. Kemal, T. W. Chan, T. C. Bruice, Proc. Natl. Acad. Sci. USA 1977, 74, 405;
21. C. Kemal, T. C. Bruice, Proc. Natl. Acad. Sci. USA 1976, 73, 995-999.
22. S.-I. Murahashi, T. Oda, Y. Masui, J. Am. Chem. Soc. 1989, 111, 5002-5003.
23. S. E. Hoegy, P. S. Mariano, Tetrahedron 1997, 53, 5027-5046;
24. C. Mazzini, J. Lebreton, R. Furstoss, J. Org. Chem. 1996, 61, 8-9;
25. H. I. X. Mager, S.-C. Tu, Tetrahedron 1994, 50, 5287-5298.
26. Y. Imada, H. Iida, S. Ono, S.-I. Murahashi, J. Am. Chem. Soc. 2003, 125, 2868-2869.
27. Y. Imada, H. Iida, S. Ono, Y. Masui, S.-I. Murahashi, Chem. Asian J. 2006, 1-2, 136-147.
28. W.-S. Li, L. M. Sayre, Tetrahedron 2001, 57, 4523-4536.
29. W.-S. Li, N. Zhang, L. M. Sayre, Tetrahedron 2001, 57, 4507-4522.
30. J. Žurek, R. Cibulka, H. Dvořáková, J. Svoboda, Tetrahedron Lett. 2010, 51, 1083-1086.
31. B. Marsh, D. R. Carbery, Tetrahedron Lett. 2010, 51, 2362-2365.
32. Y. Imada, T. Ohno, T. Naota, Tetrahedron Lett. 2007, 48, 937-939.
33. K. Holmberg, Eur. J. Org. Chem. 2007, 731-742;
34. T. Dwars, E. Paetzold, G. Oehme, Angew. Chem. 2005, 117, 7338-7364; Angew. Chem. Int. Ed. 2005, 44, 7174-7199;
35. D. M. Vriezema, M. C. Aragonés, J. A. A. W. Elemans, J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, Chem. Rev. 2005, 105, 1445-1489.
36. L. Baxová, R. Cibulka, F. Hampl, J. Mol. Catal. A 2007, 277, 53-60.
37. K. Bergstad, J.-E. Bäckvall, J. Org. Chem. 1998, 63, 6650-6655.
38. A. A. Lindén, N. Hermanns, S. Ott, L. Krüger, J.-E. Bäckvall, Chem. Eur. J. 2005, 11, 112-119;
39. A. A. Lindén, L. Krüger, J.-E. Bäckvall, J. Org. Chem. 2003, 68, 5890-5896;
40. A. B. Minidis, J.-E. Bäckvall, Chem. Eur. J. 2001, 7, 297-302;
41. S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc. 2001, 123, 1365-1371;
42. K. Bergstad, S. Y. Jonsson, J.-E. Bäckvall, J. Am. Chem. Soc. 1999, 121, 10424-10425.
43. Some examples on catalyst immobilization:
44. R. C. Rodrigues, A. Berenguer-Murcia, R. Fernández-Lafuente, Adv. Synth. Catal. 2011, 353, 2216-2238;
45. T. E. Kristensen, T. Hansen, Eur. J. Org. Chem. 2010, 3179-3204;
46. R. A. Sheldon, Adv. Synth. Catal. 2007, 349, 1289-1307;
47. D. E. deVos, B. F. Sels, P. A. Jacobs, Adv. Catal. 2001, 46, 1-87.
48. Some reviews on ionic liquids:
49. P. Domínguez de Maria, Ionic Liquids in Biotransformations and Organocatalysis: Solvents and Beyond, Wiley, Hoboken, 2012;
50. P. DomínguezdeMaria, Z. Mauregi, Curr. Opin. Chem. Biol. 2011, 15, 220-225;
51. P. C. A. G. Pinto, M. L. M. F. S. Saraiva, J. F. L. C. Lima, Anal. Sci. 2008, 24, 1231-1238;
52. N. V. Plechkova, K. R. Seddon, Chem. Soc. Rev. 2008, 37, 123-150;
53. D. MacFarlane, M. Forsyth, The Handbook of Ionic Liquids: Electrochemistry, Wiley-VCH, Weinheim, 2008;
54. X. Han, D. W. Armstrong, Acc. Chem. Res. 2007, 40, 1079-1086.
55. A. A. Lindén, M. Johansson, N. Hermanns, J.-E. Bäckvall, J. Org. Chem. 2006, 71, 3849-3853.
56. Some reviews on asymmetric sulfoxidations:
57. E. Wojaczyńska, J. Wojaczyński, Chem. Rev. 2010, 110, 4303-4356;
58. M. C. Carreño, G. Hernández-Torres, M. Ribagorda, A. Urbano, Chem. Commun. 2009, 6129-6144;
59. A. Amstrong in Enantioselective Organocatalysis (Ed.: P.I. Dalko), Wiley-VCH, Weinheim, 2007, pp.403-424;
60. H. Pellissier, Tetrahedron 2006, 62, 5559-5601;
61. J. Legros, J. R. Dehli, C. Bolm, Adv. Synth. Catal. 2005, 347, 19-31.
62. S.-I. Murahashi, Angew. Chem. 1995, 107, 2670; Angew. Chem. Int. Ed. Engl. 1995, 34, 2443;
63. S. Shinkai, T. Yamaguchi, O. Manabe, F. Toda, J. Chem. Soc. Chem. Commun. 1988, 1399.
64. R. Jurok, R. Cibulka, H. Dvořákova, F. Hampl, J. Hodačová, Eur. J. Org. Chem. 2010, 5217-5224.
65. Y. Imada, H. Iida, S.-I. Murahashi, T. Naota, Angew. Chem. 2005, 117, 1732-1734; Angew. Chem. Int. Ed. 2005, 44, 1704-1706;
66. S.-I. Murahashi, S. Ono, Y. Imada, Angew. Chem. 2002, 114, 2472-2474; Angew. Chem. Int. Ed. 2002, 41, 2366-2368.
67. Some reviews on BVMOs:
68. M. Clouthier, J. N. Pelletier, Chem. Soc. Rev. 2012, 41, 1585-1605;
69. G. deGonzalo, M. D. Mihovilovic, M. W. Fraaije, ChemBioChem 2010, 11, 2208-2231;
70. V. Alphand, R. Wohlgemuth, Curr. Org. Chem. 2010, 14, 1928-1965;
71. H. Dudek, D. E. TorresPazmiño, M. W. Fraaije, Curr. Opin. Chem. Biol. 2010, 14, 138-144;
72. M. M. Kayser, Tetrahedron 2009, 65, 947-974.
73. P. J. Gross, S. Bräse, Chem. Eur. J. 2010, 16, 12660-12667;
74. E. T. daSilva, C. A. Câmara, O. A. C. Antunes, E. J. Barreiro, C. A. M. Fraga, Synth. Commun. 2008, 38, 784-788;
75. M. Alamgir, P. S. R. Mitchell, P. K. Bowyer, N. Kumar, D. S. Black, Tetrahedron 2008, 64, 7136-7142;
76. S. Yamazaki, Chem. Lett. 1995, 127-128;
77. H. D. Dakin, Am. Chem. J. 1909, 62, 477-498.
78. S. Chen, M. S. Hossain, F. W. Foss, Jr., Org. Lett. 2012, 14, 2806-2809.
79. B. König, M. Pelka, H. Zieg, T. Ritter, H. Bouas-Laurent, R. Boneau, J.-P. Desvergne, J. Am. Chem. Soc. 1999, 121, 1681-1687;
80. B. J. Fritz, S. Kasai, K. Matsui, Photochem. Photobiol. 1987, 45, 113-117;
81. A. Bowd, P. Byrom, J. B. Hudson, J. H. Turnbull, Photochem. Photobiol. 1968, 8, 1-10.
82. R. Cibulka, R. Vasold, B. König, Chem. Eur. J. 2004, 10, 6223-6231;
83. O. Wiest, C. B. Harrison, N. J. Saettel, R. Cibulka, M. Sax, B. König, J. Org. Chem. 2004, 69, 8183-8185.
84. For thiourea-based organocatalysis and thiourea-containing compounds see:
85. S. J. Connon, Chem. Eur. J. 2006, 12, 5418-5427;
86. G. V. Oshovsky, W. Verboom, R. H. Fokkens, D. N. Reinhoudt, Chem. Eur. J. 2004, 10, 2739-2748;
87. 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.
88. J. Svoboda, H. Schmaderer, B. König, Chem. Eur. J. 2008, 14, 1854-1865.
89. R. Kuhn, F. Weygand, Chem. Ber. 1935, 68, 1282-1288.
90. H. Schmaderer, P. Hilger, R. Lechner, B. König, Adv. Synth. Catal. 2009, 351, 163-174.
91. W. Zhang, Green Chem. 2009, 11, 911-920;
92. W. Zhang, C. Cai, Chem. Commun. 2008, 5686-5694;
93. L. Zu, J. Wang, H. Li, W. Wang, Org. Lett. 2006, 8, 3077-3079;
94. Z. Dalicsek, F. Pollreisz, Á. Gömöry, T. Soos, Org. Lett. 2005, 7, 3243-3246;
95. L. V. Dinh, J. A. Gladysz, Angew. Chem. 2005, 117, 4164-4167; Angew. Chem. Int. Ed. 2005, 44, 4095-4097.
96. A. H. Haines, Methods for the Oxidation of Organic Compounds, Academic Press, London, 1988.
97. R. Lechner, B. König, Synthesis 2010, 1712-1718.
98. T. W. Gree, P. G. M. Wuts, Greene's Protective Groups in Organic Synthesis, Wiley, New York, 2006.
99. A. Taglieber, F. Schulz, F. Hollmann, M. Rusek, M. T. Reetz, ChemBioChem 2008, 9, 565-572.
100. M. W. Fraaije, J. Wu, D. P. Heuts, E. W. vanHellemond, J. H. Spelberg, D. B. Janssen, Appl. Microbiol. Biotechnol. 2005, 66, 393-400.
101. F. Hollmann, A. Taglieber, F. Schulz, M. T. Reetz, Angew. Chem. 2007, 119, 2961-2964; Angew. Chem. Int. Ed. 2007, 46, 2903-2906.
102. D. I. Perez, M. M. Grau, I. W. Arends, F. Hollmann, Chem. Commun. 2009, 6848-6850;
103. E. Churakova, M. Kluge, R. Ullrich, I. W. Arends, M. Hofrichter, F. Hollmann, Angew. Chem. 2011, 123, 10904-10907; Angew. Chem. Int. Ed. 2011, 50, 10716-10719;
104. S. Gargiulo, I. W. Arends, F. Hollmann, ChemCatChem 2011, 3, 338-342.
105. D. J. Ager, A. H. M. deVries, J. G. deVries, Chem. Soc. Rev. 2012, 41, 3340-3380;
106. M. Irfan, T. N. Glasnov, C. O. Kappe, ChemSusChem 2011, 4, 300-316; Handbook of Homogeneous Hydrogenation, Vols.1-3 (Eds.: J.G. deVries, C.J. Elsevier), Wiley-VCH, Weinheim, 2007.
107. Some methods for diimide generation:
108. M. H. Haukas, G. A. O′Doherty, Org. Lett. 2002, 4, 1771-1774;
109. D. J. Pasto, R. T. Taylor, Org. React. 1991, 40, 91-155; B. M. Trost, S. Schneider, J. Am. Chem. Soc. 1989, 111, 4430-4433;
110. T. G. Back, S. Collins, R. G. Kerr, J. Org. Chem. 1981, 46, 1564-1570.
111. Y. Imada, H. Iida, T. Naota, J. Am. Chem. Soc. 2005, 127, 14544-14555.
112. C. Smit, M. W. Fraaije, A. J. Minnaard, J. Org. Chem. 2008, 73, 9482-9485;
113. J. F. Teichert, T. denHartog, M. Hanstein, C. Smit, B. terHorst, V. Hernandez-Olmos, B. L. Feringa, A. J. Minnaard, ACS Catal. 2011, 1, 309-315.
114. Y. Imada, T. Kitagawa, T. Ohno, H. Iida, T. Naota, Org. Lett. 2010, 12, 32-35.
115. Y. Imada, H. Iida, T. Kitagawa, T. Naota, Chem. Eur. J. 2011, 17, 5908-5920.
116. Y. Yano, Y. Hoshino, W. Tagaki, Chem. Lett. 1980, 9, 749-752;
117. S. Shinkai, T. Yamashita, Y. Kusano, O. Manabe, J. Org. Chem. 1980, 45, 4947-4952.
118. A. Miyashita, Y. Suzuki, I. Nagasaki, C. Ishiguro, K.-I. Iwamoto, T. Higashino, Chem. Pharm. Bull. 1997, 45, 1254-1258;
119. S. W. Tam, L. Jimenez, F. Diederich, J. Am. Chem. Soc. 1992, 114, 1503-1505.
120. S. Iwahana, H. Iida, E. Yashima, Chem. Eur. J. 2011, 17, 8009-8013.
121. H. U. Vora, T. Rovis, J. Am. Chem. Soc. 2007, 129, 13796-13797.
122. V. Mojr, V. Herzig, V. Mojr, M. Buděšínský, R. Cibulka, T. Kraus, Chem. Commun. 2010, 46, 7599-7601.
123. L. G. Marinescu, M. Bols, Angew. Chem. 2006, 118, 4706-4709; Angew. Chem. Int. Ed. 2006, 45, 4590-4593;
124. R. Berslow, S. D. Dong, Chem. Rev. 1998, 98, 1875-1917;
125. K. Takahashi, Chem. Rev. 1998, 98, 2013-2033.
126. M. BuděŠínský, R. Cibulka, T. Kraus, Org. Biomol. Chem. 2011, 9, 7318-7326.
127. H. L. Monaco, EMBO J. 1997, 16, 1475-1483;
128. F. Müller, W. J. H. van Berkel in Chemistry and Biochemistry of Flavoenzymes, Vol.1 (Ed.: F. Müller), CRC Press, Boca Raton 1991, pp.261.
129. G. deGonzalo, C. Smit, J. Lin, A. J. Minnaard, M. W. Fraaije, Chem. Commun. 2011, 47, 11050-11052.
130. H. L. Levine, Y. Nakagawa, E. T. Kaiser, Biochem. Biophys. Res. Commun. 1977, 76, 64-70. See also: S. E. Rokita, E. T. Kaiser, J. Am. Chem. Soc. 1986, 108, 4894-4897.
131. A. Douangamath, M. Walker, S. Beismann-Driemeyer, M. C. Vega-Fernández, R. Sterner, M. Wilmanns, Structure 2002, 10, 185-193;
132. S. Beismann-Driemeyer, R. Sterner, J. Biol. Chem. 2001, 276, 20387-20396.
133. M. T. Reetz, M. Rentzsch, M. Pletsch, A. Taglibier, F. Hollman, R. J. G. Mondière, N. Dickmann, B. Höcker, S. Cerrone, M. C. Haeger, R. Sterner, ChemBioChem 2008, 9, 552-564.
134. G. Nöll, S. Trawöger, M. vonSanden-Flohe, B. Dick, M. Grininger, ChemBioChem 2009, 10, 834-837.
135. J. Jayapaul, M. Hodenius, S. Arns, W. Lederle, T. Lammers, P. Comba, F. Kiessling, J. Gaetjens, Biomaterials 2011, 32, 5863-5871.