Biocatalytic enantioselective oxidative C-C coupling by aerobic C-H activation

Angewandte Chemie - International Edition

Volumn 50, Issue 5, 2011, Pages 1068-1071

  Schrittwieser, Joerg H ^a   Resch, Verena ^a   Sattler, Johann H ^a   Lienhart, Wolf Dieter ^a   Durchschein, Katharina ^a   Winkler, Andreas ^b   Gruber, Karl ^a   MacHeroux, Peter ^b   Kroutil, Wolfgang ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

alkaloids; asymmetric synthesis; C C coupling; C H activation; enzyme catalysis

Indexed keywords

ALKALOIDS; ASYMMETRIC SYNTHESIS; C-C COUPLING; C-H ACTIVATION; ENZYME CATALYSIS;

ACTIVATION ANALYSIS; CATALYSIS; ENZYMES; NITROGEN COMPOUNDS;

METABOLITES;

BENZYLISOQUINOLINE DERIVATIVE; BERBERINE DERIVATIVE; N DEMETHYLASE; OXYGEN; RETICULINE OXIDASE;

ARTICLE; BIOCATALYSIS; CHEMISTRY; COMBINATORIAL CHEMISTRY; OXIDATIVE COUPLING; STEREOISOMERISM; SYNTHESIS;

BENZYLISOQUINOLINES; BERBERINE ALKALOIDS; BIOCATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; OXIDATIVE COUPLING; OXIDOREDUCTASES, N-DEMETHYLATING; OXYGEN; STEREOISOMERISM;

EID: 79251548859     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006268     Document Type: Article

References (72)

1. W. Liu, H. Cao, A. Lei, Angew. Chem. 2010, 122, 2048-2052
2. Angew. Chem. Int. Ed. 2010, 49, 2004-2008
3. K. Godula, D. Sames, Science 2006, 312, 67-72.
4. Y. Wei, H. Zhao, J. Kan, W. Su, M. Hong, J. Am. Chem. Soc. 2010, 132, 2522-2523
5. Z.-H. Guan, Z.-Y. Yan, Z.-H. Ren, X.-Y. Liu, Y.-M. Liang, Chem. Commun. 2010, 46, 2823-2825
6. M. Chen, X. Zheng, W. Li, J. He, A. Lei, J. Am. Chem. Soc. 2010, 132, 4101-4103
7. F. Benfatti, M. G. Capdevila, L. Zoli, E. Benedetto, P. G. Cozzi, Chem. Commun. 2009, 5919-5921
8. Z. Li, L. Cao, C.-J. Li, Angew. Chem. 2007, 119, 6625-6627
9. Angew. Chem. Int. Ed. 2007, 46, 6505-6507.
10. M. Pohl, A. Liese, in Biocatalysis in the Pharmaceutical and Biotechnology Industry (Ed.:, R. N. Patel,), CRC Press, Boca Raton, 2007, pp. 661-676.
11. P. Clapés, W.-D. Fessner, G. A. Sprenger, A. K. Samland, Curr. Opin. Chem. Biol. 2010, 14, 154-167
12. D. G. Gillingham, P. Stallforth, A. Adibekian, P. H. Seeberger, D. Hilvert, Nat. Chem. 2010, 2, 102-105
13. S. M. Dean, W. A. Greenberg, C.-H. Wong, Adv. Synth. Catal. 2007, 349, 1308-1320
14. W.-D. Fessner, S. Jennewein, in Biocatalysis in the Pharmaceutical and Biotechnology Industry (Ed.:, R. N. Patel,), CRC Press, Boca Raton, 2007, pp. 363-400.
15. R. Wohlgemuth, J. Mol. Catal. B 2009, 61, 23-29.
16. J. Holt, U. Hanefeld, Curr. Org. Synth. 2009, 6, 15-37
17. F. Effenberger, S. Förster, C. Kobler, in Biocatalysis in the Pharmaceutical and Biotechnology Industry (Ed.:, R. N. Patel,), CRC Press, Boca Raton, 2007, pp. 677-698
18. T. Purkarthofer, W. Skranc, C. Schuster, H. Griengl, Appl. Microbiol. Biotechnol. 2007, 76, 309-320.
19. Selected examples
20. C. Dresen, M. Richter, M. Pohl, S. Lüdeke, M. Müller, Angew. Chem. 2010, 122, 6750-6753
21. Angew. Chem. Int. Ed. 2010, 49, 6600-6603
22. P. Lehwald, M. Richter, C. Röhr, H.-w. Liu, M. Müller, Angew. Chem. 2010, 122, 2439-2442
23. Angew. Chem. Int. Ed. 2010, 49, 2389-2392
24. M. Müller, D. Gocke, M. Pohl, FEBS J. 2009, 276, 2894-2904.
25. For use of methyl transferases, see
26. H. Stecher, M. Tengg, B. J. Ueberbacher, P. Remler, H. Schwab, H. Griengl, M. Gruber-Khadjawi, Angew. Chem. 2009, 121, 9710-9712
27. Angew. Chem. Int. Ed. 2009, 48, 9546-9548
28. for hydroxynitrile lyase catalyzed Henry reaction, see:, T. Purkarthofer, K. Gruber, M. Gruber-Khadjawi, K. Waich, W. Skranc, D. Mink, H. Griengl, Angew. Chem. 2006, 118, 3532-3535
29. Angew. Chem. Int. Ed. 2006, 45, 3454-3456
30. for opening of epoxides with cyanide catalyzed by halohydrin dehalogenases, see:, M. M. Elenkov, B. Hauer, D. B. Janssen, Adv. Synth. Catal. 2006, 348, 579-585
31. for peroxidase-catalyzed coupling of solid-supported ortho- methoxyphenols, see:, S. Antoniotti, J. S. Dordick, Adv. Synth. Catal. 2005, 347, 1119-1124
32. for enzymatic aromatic prenylation, see:, L. A. Wessjohan, B. Sontag, M.-A. Desoy, in Bioorganic Chemistry (Eds.:, U. Diederichsen, T. K. Lindhorst, B. Westermann, L. A. Wessjohann,), Wiley-VCH, Weinheim, 1999, pp. 79-88.
33. Only laccases have been employed to activate mainly phenolic compounds for radical C-C bond formation. For recent reviews, see
34. S. Riva, Trends Biotechnol. 2006, 24, 219-226
35. S. Witayakran, A. J. Ragauskas, Adv. Synth. Catal. 2009, 351, 1187-1209.
36. A. Winkler, A. Lyskowski, S. Riedl, M. Puhl, T. M. Kutchan, P. Macheroux, K. Gruber, Nat. Chem. Biol. 2008, 4, 739-741.
37. S. Paul, N. Naotaka, M. H. Zenk, Phytochemistry 1985, 24, 2577-2583.
38. E. Rink, H. Boehn, FEBS Lett. 1975, 49, 396-399.
39. A. Winkler, F. Hartner, T. M. Kutchan, A. Glieder, P. Macheroux, J. Biol. Chem. 2006, 281, 21276-21285.
40. A. Winkler, K. Motz, S. Riedl, M. Puhl, P. Macheroux, K. Gruber, J. Biol. Chem. 2009, 284, 19993-20001.
41. A. Winkler, M. Puhl, H. Weber, T. M. Kutchan, K. Gruber, P. Macheroux, Phytochemistry 2009, 70, 1092-1097.
42. J.-M. Oger, A. Fardeau, P. Richomme, H. Guinaudeau, A. Fournet, Can. J. Chem. 1993, 71, 1128-1135.
43. Full details about optimization of the reaction and solvent study will be published in due course.
44. E. D. Cox, J. M. Cook, Chem. Rev. 1995, 95, 1797-1842.
45. Reactions were performed in the dark to minimize photo-induced degradation
46. W. Holzer, J. Shirdel, P. Zirak, A. Penzkofer, P. Hegemann, R. Deutzmann, E. Hochmuth, Chem. Phys. 2005, 308, 69-78; as well as other photo-induced side-reactions, for example, reduction of flavin
47. M. Mifsud Grau, J. C. van der Toorn, L. G. Otten, P. Macheroux, A. Taglieber, F. E. Zilly, I. W. C. E. Arends, F. Hollmann, Adv. Synth. Catal. 2009, 351, 3279-3286.
48. J. L. L. Rakels, A. J. J. Straathof, J. J. Heijnen, Enzyme Microb. Technol. 1993, 15, 1051-1056.
49. M. W. Fraaije, A. Mattevi, Nat. Chem. Biol. 2008, 4, 719-721
50. J. Keasling, Nat. Chem. Biol. 2008, 4, 524-525
51. K. W. Bentley, The Isoquinoline Alkaloids, Harwood, Amsterdam, 1998.
52. M. L. Martin, M. T. Diaz, M. J. Montero, P. Prieto, L. S. Roman, D. Cortes, Planta Med. 1993, 59, 63-67.
53. S. Chulia, M. D. Ivorra, C. Lugnier, E. Vila, M. A. Noguera, P. DOcon, Br. J. Pharmacol. 1994, 113, 1377-1385.
54. J.-M. Gao, W.-T. Liu, M.-L. Li, H.-W. Liu, X.-C. Zhang, Z.-X. Li, J. Mol. Struct. 2008, 892, 466-469, and references cited therein
55. W. J. Eisenreich, G. Hofner, F. Bracher, Nat. Prod. Res. 2003, 17, 437-440
56. Y. Kashiwada, A. Aoshima, Y. Ikeshiro, Y.-P. Chen, H. Furukawa, M. Itoigawa, T. Fujioka, K. Mihashi, L. M. Cosentino, S. L. Morris-Natschke, K.-H. Lee, Bioorg. Med. Chem. 2005, 13, 443-448
57. F. N. Ko, J. H. Guh, S. M. Yu, Y. S. Hou, Y. C. Wu, C. M. Teng, Br. J. Pharmacol. 1994, 112, 1174-1180.
58. J. Li, G. Jin, J. Shen, R. Ji, Drugs Future 2006, 31, 379-384.
59. M. Chrzanowska, M. D. Rozwadowska, Chem. Rev. 2004, 104, 3341-3370.
60. P.-C. Yan, J.-H. Xie, G.-H. Hou, L.-X. Wang, Q.-L. Zhou, Adv. Synth. Catal. 2009, 351, 3243-3250
61. S.-M. Lu, Y.-Q. Wang, X.-W. Han, Y.-G. Zhou, Angew. Chem. 2006, 118, 2318-2321
62. Angew. Chem. Int. Ed. 2006, 45, 2260-2263
63. M. Kitamura, Y. Hsiao, M. Ohta, M. Tsukamoto, T. Ohta, H. Takaya, R. Noyori, J. Org. Chem. 1994, 59, 297-310.
64. C. Shi, I. Ojima, Tetrahedron 2007, 63, 8563-8570.
65. C. Dubs, Y. Hamashima, N. Sasamoto, T. M. Seidel, S. Suzuki, D. Hashizume, M. Sodeoka, J. Org. Chem. 2008, 73, 5859-5871
66. N. Sasamoto, C. Dubs, Y. Hamashima, M. Sodeoka, J. Am. Chem. Soc. 2006, 128, 14010-14011
67. A. M. Taylor, S. L. Schreiber, Org. Lett. 2006, 8, 143-146
68. S. Wang, C. T. Seto, Org. Lett. 2006, 8, 3979-3982
69. T. Itoh, M. Miyazaki, H. Fukuoka, K. Nagata, A. Ohsawa, Org. Lett. 2006, 8, 1295-1297.
70. J. M. Woodley, Trends Biotechnol. 2008, 26, 321-327
71. D. J. Pollard, J. M. Woodley, Trends Biotechnol. 2007, 25, 66-73
72. H. E. Schoemaker, D. Mink, M. G. Wubbolts, Science 2003, 299, 1694-1697.