Biomimetic hydroxylation of nonactivated CH2 groups with copper complexes and molecular oxygen

Angewandte Chemie - International Edition

Volumn 42, Issue 28, 2003, Pages 3240-3244

  Schönecker, Bruno ^a   Zheldakova, Tatjana ^b   Liu, Yong ^a   Kötteritzsch, Manuela ^a   Günther, Wolfgang ^a   Görls, Helmar ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

C H activation; Copper; Hydroxylation; O O activation; Steroids

Indexed keywords

BIOMIMETIC MATERIALS; COPPER COMPOUNDS; HYDROXYLATION; KETONES; OXYGEN; REDUCTION;

BIOMIMETIC HYDROXYLATION;

COMPLEXATION;

12BETA HYDROXY 17 KETONE; 17BETA,12BETA AMINO ALCOHOL; AMINOALCOHOL; AMMONIA; BETA CYCLODEXTRIN; COPPER COMPLEX; DOPAMINE BETA MONOOXYGENASE; INDAN DERIVATIVE; KETONE DERIVATIVE; LIGAND; METAL COMPLEX; METHYL CHLORIDE; METHYL GROUP; MONOPHENOL MONOOXYGENASE; OXYGEN; PYRIDINE DERIVATIVE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; CONFORMATION; CRYSTAL STRUCTURE; DIASTEREOISOMER; HYDROXYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0041764486     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250815     Document Type: Article

References (62)

1. a) N. Kitajima, Y. Morooka, Chem. Rev. 1994, 94, 737-757;
2. b) W. Kaim, J. Rall, Angew. Chem. 1996, 108, 47-64; Angew. Chem. Int. Ed. Engl. 1996, 35, 43-60;
3. b) W. Kaim, J. Rall, Angew. Chem. 1996, 108, 47-64; Angew. Chem. Int. Ed. Engl. 1996, 35, 43-60;
4. c) M. Pascaly, I. Jolk, B. Krebs, Chem. Unserer Zeit 1999, 33, 334-341.
5. a) K. D. Karlin, S. Kaderli, A. D. Zuberbühler, Acc. Chem. Res. 1997, 30, 139-147;
6. b) L. Que, Jr., W. B. Tolman, Angew. Chem. 2002, 114, 1160-1185; Angew. Chem. Int. Ed. 2002, 41, 1114-1137;
7. b) L. Que, Jr., W. B. Tolman, Angew. Chem. 2002, 114, 1160-1185; Angew. Chem. Int. Ed. 2002, 41, 1114-1137;
8. c) R. Than, A. Feldmann, B. Krebs, Coord. Chem. Rev. 1999, 182, 211-241;
9. d) P. L. Holland, W. P. Tolman, Coord. Chem. Rev. 1999, 190-192, 855- 869;
10. e) S. Schindler, Eur. J. Inorg. Chem. 2000, 2311-2326;
11. f) A.G. Blackman, W. P. Tolman, Struct. Bonding (Berlin) 2000, 97, 179-211;
12. g) I. Blain, M. Giorgi, I. DeRiggi, M. Reglier, Eur. J. Inorg. Chem. 2001, 205-211.
13. a) K. D. Karlin, J. C. Hayes, Y. Gultneh, R. W. Cruse, J. W. McKown, J. P. Hutchinson, J. Zubieta, J. Am. Chem. Soc. 1984, 106, 2121-2128;
14. b) O. J. Gelling, F. van Bolhuis, A. Meetsma, B. L. Feringa, J. Chem. Soc. Chem. Commun. 1988, 552-554;
15. c) L. Casella, M. Gullotti, G. Pallanza, L. Rigoni, J. Am. Chem. Soc. 1988, 110, 4221-4227;
16. d) R. Menif, A. E. Martell, J. Chem. Soc. Chem. Commun. 1989, 1521-1523;
17. e) O. J. Gelling, B. L. Feringa, J. Am. Chem. Soc. 1990, 112, 7599-7604;
18. f) R. Menif, A. E. Martell, P. J. Squattrito, A. Clearfield, Inorg. Chem. 1990, 29, 4723-4729;
19. g) T. N. Sorrell, V. A. Vankai, M. L. Garrity, Inorg. Chem. 1991, 30, 207-210;
20. h) T. N. Sorrell, M. L. Garrity, Inorg. Chem. 1991, 30, 210-215;
21. i) M. Becker, S. Schindler, R. van Eldik, Inorg. Chem. 1994, 33, 5370-5371;
22. j) S. Ryan, H. Adams, D. E. Fenton, M. Becker, S. Schindler, Inorg. Chem. 1998, 37, 2134-2140;
23. k) M. Becker, S. Schindler, K. D. Karlin, T. A. Kaden, S. Kaderli, T. Palanche, A. D. Zuberbühler, Inorg. Chem. 1999, 38, 1989-1995;
24. l) E. Pidcock, H. V. Obias, C. X. Zhang, K. D. Karlin, E. I. Solomon, J. Am. Chem. Soc. 1998, 120, 7841-7847;
25. m) P. L. Holland, K. R. Rodgers, W. B. Tolman, Angew. Chem. 1999, 111, 1210-1213; Angew. Chem. Int. Ed. 1999, 38, 1139-1142;
26. m) P. L. Holland, K. R. Rodgers, W. B. Tolman, Angew. Chem. 1999, 111, 1210-1213; Angew. Chem. Int. Ed. 1999, 38, 1139-1142;
27. n) L. Santagostini, M. Gullotti, E. Monzani, L. Casella, R. Dillinger, F. Tuczek, Chem. Eur. J. 2000, 6, 519-522;
28. o) S. Itoh, H. Kumei, M. Taki, S. Nagatomo, T. Kitagawa, S. Fukuzumi, J. Am. Chem. Soc. 2001, 123, 6708-6709.
29. a) E. Amadei, E. H. Alilou, F. Eydoux, M. Pierrot, M. Reglier, B. Waegell, J. Chem. Soc. Chem. Commun. 1992, 1782-1784;
30. b) S. Itoh, T. Kondo, M. Komatsu, Y. Ohshiro, C. Li, N. Kanehisa, Y. Kai, S. Fukuzumi, J. Am. Chem. Soc. 1995, 117, 4714-4715;
31. c) I. Blain, P. Bruno, M. Giorgi, E. Lojou, D. Lexa, M. Reglier, Eur. J. Inorg. Chem. 1998, 1297-1304;
32. d) S. Itoh, H. Nakao, L. M. Berreau, T. Kondo, M. Komatsu, S. Fukuzumi, J. Am. Chem. Soc. 1998, 120, 2890-2899;
33. e) S. Itoh, M. Taki, H. Nakao, P. L. Holland, W. B. Tolman, L. Que, Jr., S. Fukuzumi, Angew. Chem. 2000, 112, 409-411; Angew. Chem. Int. Ed. 2000, 39, 398-400.
34. e) S. Itoh, M. Taki, H. Nakao, P. L. Holland, W. B. Tolman, L. Que, Jr., S. Fukuzumi, Angew. Chem. 2000, 112, 409-411; Angew. Chem. Int. Ed. 2000, 39, 398-400.
35. I. Blain, M. Giorgi, I. De Riggi, M. Reglier, Eur. J. Inorg. Chem. 2000, 393-398.
36. a) M. Gonschior, M. Kötteritzsch, M. Rost, B. Schönecker, R. Wyrwa, Tetrahedron: Asymmetry 2000, 11, 2159-2182;
37. b) St. Diekmann, J. Weston, E. Anders, W. Boland, B. Schönecker, T. Hettmann, J. von Langen, S. Erhardt, M. Mauksch, M. Bräuer, C. Beckmann, M. Rost, P. Sperling, E. Heinz, Rev. Mol. Biotechnol. 2002, 90, 73-94;
38. c) M. Dubs, R. Krieg, H. Görls, B. Schönecker, Steroids 2000, 65, 305-318;
39. d) R. Krieg, M. Dubs, H. Görls, B. Schönecker, Chem. Ber. 1996, 129, 1497-1501.
40. a) K. D. Karlin, D.-H. Lee, S. Kaderli, A. D. Zuberbühler, Chem. Commun. 1997, 475-476;
41. b) V. Mahadevan, M. J. Henson, E. I. Solomon, T. D. P. Stack, J. Am. Chem. Soc. 2000, 122, 10249-10250;
42. c) H. Hayashi, S. Fujinami, S. Nagatomo, S. Ogo, M. Suzuki, A. Uehara, Y. Watanabe, T. Kitagawa, J. Am. Chem. Soc. 2000, 122, 2124-2125;
43. d) Y. Shimazaki, T. Nogami, F. Tani, A. Odani, O. Yamauchi, Angew. Chem. 2001, 113, 3977-3980; Angew. Chem. Int. Ed. 2001, 40, 3859-3862;
44. d) Y. Shimazaki, T. Nogami, F. Tani, A. Odani, O. Yamauchi, Angew. Chem. 2001, 113, 3977-3980; Angew. Chem. Int. Ed. 2001, 40, 3859-3862;
45. e) H.-C. Liang, C. X. Zhang, M. J. Henson, R. D. Sommer, K. R. Hatwell, S. Kaderli, A. D. Zuberbühler, A. L. Rheingold, E. I. Solomon, K. D. Karlin, J. Am. Chem. Soc. 2002, 124, 4170-4171;
46. f) M. Taki, S. Teramae, S. Nagatomo, Y. Tachi, T. Kitagawa, S. Itoh, S. Fukuzumi, J. Am. Chem. Soc. 2002, 124, 6367-6377.
47. S. Mahapatra, J. A. Halfen, W. B. Tolman, J. Am. Chem. Soc. 1996, 118, 11575-11586.
48. a) R. Breslow, J. Yan, S. Belvedere, Tetrahedron Lett. 2002, 43, 363-365;
49. b) R. Breslow, J. Yang, J. Yan, Tetrahedron 2002, 58, 653-659.
50. a) R. Breslow, Acc. Chem. Res. 1980, 13, 170-177;
51. b) R. Breslow, Chemtracts: Org. Chem. 1988, 333-348;
52. c) E. J. Parish, N. Aksara, T. L. Boos, Lipids 1997, 32, 1325-1330.
53. P. A. Grieco, T. L. Stuk, J. Am. Chem. Soc. 1990, 112, 7799-7801.
54. a) M. M. Coombs, R. H. Roderick, J. Chem. Soc. C 1967, 1819-1821;
55. b) , US Patent 3324153, 1967.
56. L. F. Fieser, M. Fieser, Steroide, VCH, Weinheim, 1961, pp. 693-705.
57. G. Majetich, K. Wheless, Tetrahedron 1995, 51, 7095-7129.
58. COLLECT, Data Collection Software, Nonius B.V., Netherlands, 1998.
59. "Processing of X-Ray Diffraction Data Collected in Oscillation Mode": Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326.
60. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473.
61. G. M. Sheldrick, SHELXL-97, University of Göttingen, Göttingen (Germany), 1993.
62. CCDC-199645, -199646, and -204451 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-036-033; or deposit@ccdc.cam.ac.uk).