Cytochrome P450-catalyzed insertion of carbenoids into N-H bonds

Chemical Science

Volumn 5, Issue 2, 2014, Pages 598-601

  Wang, Z Jane ^a   Peck, Nicole E ^a   Renata, Hans ^a   Arnold, Frances H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION PRODUCTS; BACILLUS MEGATERIUM; CARBENOIDS; CYTOCHROME P450; DIAZO COMPONENTS; N-H INSERTION; SYNTHETIC CHEMISTRY;

BACTERIOLOGY; BIOCHEMISTRY;

CATALYSIS;

EID: 84891459977     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc52535j     Document Type: Article

References (40)

1. (a) P. J. Yates, J. Am. Chem. Soc., 1952, 74, 5376;
2. (b) T. Saegusa, Y. Ito, S. Kobayashi, K. Hirota and T. Shimizu, Tetrahedron Lett., 1966, 7, 6131;
3. (c) M. P. Doyle, M. A. McKervey and T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, Wiley, New York, 1998, ch. 8.2.
4. (a) C. Bolm, A. Kasyan, K. Drauz, K. Gunther and G. Raabe, Angew. Chem., Int. Ed., 2000, 39, 2288;
5. (b) F. Davis, T. Fang and R. Goswami, Org. Lett., 2002, 4, 1599;
6. (c) K. Yamazaki and Y. Kondo, Chem. Commun., 2002, 210;
7. (d) K. E. Bashford, A. L. Cooper, P. D. Kane, C. J. Moody, S. Muthusamy and E. Swann, J. Chem. Soc., Perkin Trans. 1, 2002, 1672;
8. (e) S.-H. Lee, B. Clapham, G. Koch, J. Zimmerman and K. D. Janda, J. Comb. Chem., 2003, 5, 188;
9. (f) A. C. B. Burtoloso and C. R. D. Correia, Tetrahedron Lett., 2004, 45, 3355;
10. (g) J. R. Davies, P. D. Kane and C. J. Moody, Tetrahedron, 2004, 60, 3967;
11. (h) H. Matsushita, S.-H. Lee, K. Yoshida, B. Clapham, G. Koch, J. Zimmerman and K. Janda, Org. Lett., 2004, 6, 4627;
12. (i) I. Aviv and Z. Gross, Chem. Commun., 2006, 4477;
13. (j) B. Liu, S.-F. Zhu, W. Zhang, C. Chen and Q.-L. Zhou, J. Am. Chem. Soc., 2007, 129, 5834.
14. (a) R. Ratcliffe, T. Salzmann and B. Christensen, Tetrahedron Lett., 1980, 21, 31;
15. (b) T. N. Salzmann, R. W. Ratcliffe, B. G. Christensen and F. A. Bouffard, J. Am. Chem. Soc., 1980, 102, 6161.
16. (a) S.-F. Zhu, B. Xu, G.-P. Wang and Q.-L. Zhou, J. Am. Chem. Soc., 2012, 134, 436;
17. (b) B. J. Anding and L. K. Woo, Organometallics, 2013, 32, 2599-2607.
18. For selected recent examples see: (a) S. Bachmann, D. Fielenbach and K. A. Jorgensen, Org. Biomol. Chem., 2004, 2, 3044;
19. (b) E. C. Lee and G. C. Fu, J. Am. Chem. Soc., 2007, 129, 12066;
20. (c) M. E. Morilla, M. M. Díaz-Requejo, T. R. Belderrain, M. C. Nicasio, S. Trofimenko and P. Pérez, Chem. Commun., 2002, 2998;
21. (d) M. Moyer, P. Feldman and H. Rapoport, J. Org. Chem., 1985, 50, 5223;
22. (e) M. Kantam, B. Neelima and C. Reddy, J. Mol. Catal. A: Chem., 2006, 256, 269;
23. (f) Z. Zhang and J. Wang, Tetrahedron, 2008, 64, 6577.
24. S. S. So and A. E. Mattson, J. Am. Chem. Soc., 2012, 134, 8798.
25. (a) Z. T. Ball, Acc. Chem. Res., 2013, 46, 560-570;
26. (b) D. Gillingham and N. Fei, Chem. Soc. Rev., 2013, 42, 4918.
27. For P450-catalyzed cyclopropanation, see (a) P. Coelho, E. Brustad, A. Kannan and F. H. Arnold, Science, 2013, 339, 307;
28. (b) P. Coelho, Z. J. Wang, M. Energ, S. A. Baril, A. Kannan, F. H. Arnold and E. Brustad, Nat. Chem. Biol., 2013, 9, 485;
29. (c) As a comparison for Rh cyclopropanation, see: H. M. L. Davies and C. Venkataramani, Org. Lett., 2003, 5, 1403.
30. (a) T. Ye and M. A. McKervey, Chem. Rev., 1994, 94, 1091;
31. (b) C. J. Moody, Angew. Chem., Int. Ed., 2007, 46, 9148;
32. (c) S.-F. Zhu and Q.-L. Zhou, Acc. Chem. Res., 2012, 45, 1365, and references therein.
33. (a) L. K. Baumann, H. M. Mbuvi, G. Du and L. K. Woo, Organometallics, 2007, 26, 3995;
34. (b) H. M. Mbuvi, E. R. Klobuskowski, G. Roberts and L. K. Woo, J. Porphyrins Phthalocyanines, 2010, 14, 284, also see ref. 4b.
35. J. C. Lewis, S. M. Mantovani, Y. Fu, C. D. Snow, R. S. Komor, C. H. Wong and F. H. Arnold, ChemBioChem, 2010, 11, 2502.
36. W. A. Johnston, D. J. B. Hunter, C. J. Noble, G. R. Hanson, J. E. Stok, M. A. Hayes, J. J. De Voss and E. M. J. Gillam, J. Biol. Chem., 2011, 286, 40750.
37. S. Chanthamath, S. Thongjareun, K. Shibatomi and S. Iwasa, Tetrahedron Lett., 2012, 53, 4862.
38. (a) K. Faber, Biotransformation in Organic Chemistry, Springer, New York, 2004;
39. (b) J. D. Rozzell, Bioorg. Med. Chem., 1999, 7, 2253;
40. (c) A. J. J. Straathof, S. Panke and A. Schmid, Curr. Opin. Biotechnol., 2002, 13, 548.