Copper-phthalocyanine conjugates of serum albumins as enantioselective catalysts in Diels-Alder reactions

Angewandte Chemie - International Edition

Volumn 45, Issue 15, 2006, Pages 2416-2419

  Reetz, Manfred T ^a   Jiao, Ning ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Asymmetric catalysis; Copper; Cycloaddition; Phthalocyanines; Proteins

Indexed keywords

ASYMMETRIC CATALYSIS; CYCLOADDITION; PHTHALOCYANINES;

CATALYSIS; CATALYSTS; COPPER COMPOUNDS; REACTION KINETICS;

PROTEINS;

INDOLE DERIVATIVE; ORGANOMETALLIC COMPOUND; PHTHALOCYANINE COPPER; SERUM ALBUMIN;

ANIMAL; ARTICLE; CATALYSIS; CATTLE; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; STEREOISOMERISM;

ANIMALS; CATALYSIS; CATTLE; HUMANS; INDOLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SERUM ALBUMIN; STEREOISOMERISM;

EID: 33745664610     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200504561     Document Type: Article

References (62)

1. a) M. E. Wilson, G. M. Whitesides, J. Am. Chem. Soc. 1978, 100, 306-307;
2. b) C.-C. Lin, C.-W. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 1999, 10, 1887-1893;
3. c) J. Collot, J. Gradinaru, N. Humbert, M. Skander, A. Zocchi, T. R. Ward, J. Am. Chem. Soc. 2003, 125, 9030-9031;
4. d) T. R. Ward, Chem. Eur. J. 2005, 11, 3798-3804;
5. e) G. Klein, N. Humbert, J. Gradinaru, A. Ivanova, F. Gilardoni, U. E. Rusbandi, T. R. Ward, Angew. Chem. 2005, 117, 7942-7945;
6. Angew. Chem. Int. Ed. 2005, 44, 7764-7767;
7. f) M. T. Reetz, M. Rentzsch, A. Pletsch, M. Maywald, Chimia 2002, 56, 721-723;
8. g) D. Qi, C.-M. Tann, D. Haring, M. D. Distefano, Chem. Rev. 2001, 101, 3081-3111;
9. h) M. Ohashi, T. Koshiyama, T. Ueno, M. Yanase, H. Fujii, Y. Watanabe, Angew. Chem. 2003, 115, 1035-1038;
10. Angew. Chem. Int. Ed. 2003, 42, 1005-1008;
11. i) J. R. Carey, S. K. Ma, T. D. Pfister, D. K. Garner, H. K. Kim, J. A. Abramite, Z. Wang, Z. Guo, Y. Lu, J. Am. Chem. Soc. 2004, 126, 10812-10813;
12. j) B. G. Davis, Curr. Opin. Biotechnol. 2003, 14, 379-386;
13. k) T. Ueno, T. Koshiyama, M. Ohashi, K. Kondo, M. Kono, A. Suzuki, T. Yamane, Y. Watanabe, J. Am. Chem. Soc. 2005, 127, 6556-6562;
14. l) C. A. Kruithof, M. A. Casado, G. Guillena, M. R. Egmond, A. van der Kerk-van Hoof, A. J. R. Heck, R. J. M. Klein Gebbink, G. van Koten, Chem. Eur. J. 2005, 11, 6869-6877;
15. m) See also: D. Hilvert, E. T. Kaiser, Biotechnol. Genet. Eng. Rev. 1987, 4, 297-318;
16. n) E. T. Kaiser, Angew. Chem. 1988, 100; 945-955;
17. Angew. Chem. Int. Ed. Engl. 1988, 27, 913-922.
18. a) S. Otto, J. B. F. N. Engberts, J. Am. Chem. Soc. 1999, 121, 6798-6806;
19. b) S. Otto, G. Boccaletti, J. B. F. N. Engberts, J. Am. Chem. Soc. 1998, 120, 4238-4239.
20. G. Roelfes, B. L. Feringa, Angew. Chem. 2005, 117, 3294-3296;
21. Angew. Chem. Int. Ed. 2005, 44, 3230-3232.
22. K. R. Rao, T. N. Srinivasan, N. Bhanumathi, Tetrahedron Lett. 1990, 31, 5959-5960.
23. a) S. Colonna, A. Manfredi, R. Annunziata, Tetrahedron Lett. 1988, 29, 3347-3350;
24. for other types of reactions in the presence of BSA, see: b) R. Annunziata, S. Banfi, S. Colonna, Tetrahedron Lett. 1985, 26, 2471-2474;
25. c) S. Colonna, A. Manfredi, M. Spadoni, Tetrahedron Lett. 1987, 28, 1577-1580;
26. d) S. Colonna, N. Gaggero, M. Leone, Tetrahedron 1991, 47, 8385-8398;
27. e) for a review on stereoselective oxidations and reductions catalyzed by nonredox proteins, see: S. V. Dzyuba, A. M. Klibanov, Tetrahedron: Asymmetry 2004, 15, 2771-2777.
28. a) A. Ichihara, H. Oikawa, Curr. Org. Chem. 1998, 2, 365-394;
29. b) G. Pohnert, ChemBioChem 2001, 2, 873-875;
30. c) G. Pohnert, ChemBioChem 2003, 4, 713-715;
31. d) E. M. Stocking, R. M. Williams, Angew. Chem. 2003, 115, 3186-3223;
32. Angew. Chem. Int. Ed. 2003, 42, 3078-3115;
33. e) J. Kennedy, K. Auclair, S. G. Kendrew, C. Park, J. C. Vederas, C. R. Hutchinson, Science 1999, 284, 1368-1372;
34. f) K. Auclair, A. Sutherland, J. Kennedy, D. J. Witter, J. P. Van den Heever, C. R. Hutchinson, J. C. Vederas, J. Am. Chem. Soc. 2000, 122, 11519-11520;
35. g) H. Oikawa, K. Watanabe, K. Yagi, S. Ohashi, T. Mie, A. Ichihara, M. Honma, Tetrahedron Lett. 1999, 40, 6983-6986;
36. h) H. Oikawa, Bull. Chem. Soc. Jpn. 2005, 78, 537-554.
37. a) F. E. Romesberg, B. Spiller, P. G. Schultz, R. C. Stevens, Science 1998, 279, 1929-1933 ;
38. b) A. Heine, E. A. Stura, J. T. YliKauhaluoma, C. Gao, Q. Deng, B. R. Beno, K. N. Houk, K. D. Janda, I. A. Wilson, Science 1998, 279, 1934-1940.
39. a) B. Seelig, S. Keiper, F. Stuhlmann, A. Jäschke, Angew. Chem. 2000, 112, 4764-4768;
40. Angew. Chem. Int. Ed. 2000, 39, 4576-4579;
41. b) F. Stuhlmann, A. Jäschke, J. Am. Chem. Soc. 2002, 124, 3238-3244;
42. c) A. Serganov, S. Keiper, L. Malinina, V. Tereshko, E. Skripkin, C. Höbartner, A. Polonskaia, A. Tuân Phan, R. Wombacher, R. Micura, Z. Dauter, A. Jäschke, D. J. Patel, Nat. Struct. Mol. Biol. 2005, 12, 218-224.
43. a) T. Peters, All about Albumin: Biochemistry, Genetics and Medical Applications, Academic Press, San Diego, 1996;
44. 2- and CO-binding properties of artificial hemoproteins formed by complexing Fe-protoporphyrin IX with HSA mutants, see: T. Komatsu, N. Ohmichi, A. Nakagawa, P. A. Zunszain, S. Curry, E. Tsuchida, J. Am. Chem. Soc. 2005, 127, 15933-15942, and references therein.
45. T. Kokubo, T. Sugimoto, T. Uchida, S. Tanimoto, M. Okano, J. Chem. Soc. Chem. Commun. 1983, 769-770.
46. A. Mahammed, Z. Gross, J. Am. Chem. Soc. 2005, 127, 2883-2887.
47. a) A. Mahammed, H. B. Gray, J. J. Weaver, K. Sorasaenee, Z. Gross, Bioconjugate Chem. 2004, 15, 738-746, and references therein;
48. b) T. G. Gantchev, R. Ouellet, J. E. van Lier, Arch. Biochem. Biophys. 1999, 366, 21-30;
49. c) S. Chatterjee, T. S. Srivastava, J. Porphyrins Phthalocyanines 2000, 4, 147-157;
50. d) Y. Ding, B. Lin, C. W. Huie, Electrophoresis 2001, 22, 2210-2216;
51. e) U. Kragh-Hansen, V. T. G. Chuang, M. Otagiri, Biol. Pharm. Bull. 2002, 25, 695-704.
52. a) P. A. Zunszain, J. Ghuman, T. Komatsu, E. Tsuchida, S. Curry, BMC Struct. Biol. 2003, 3, 6;
53. See also: b) M. Wardell, Z. Wang, J. X. Ho, J. Robert, F. Ruker, J. Ruble, D. C. Carter, Biochem. Biophys. Res. Commun. 2002, 291, 813-819;
54. c) M. Dockal, D. C. Carter, F. Rüker, J. Biol. Chem. 1999, 274, 29303-29310.
55. J. C. Cassatt, J. Biol. Chem. 1973, 248, 6129-6134, and references therein.
56. We thank K. Angermund for generating Figure 2.
57. [2,3] which means that this task is also necessary before a detailed discussion of the source of enantioselectivity is possible.
58. a) M. T. Reetz, Tetrahedron 2002, 58, 6595-6602;
59. b) M. T. Reetz, Proc. Natl. Acad. Sci. USA 2004, 101, 5716-5722;
60. c) M. T. Reetz, DE-A 101 29 187.6, 2001.
61. a) K. A. Barr, S. A. Hopkins, K. Sreekrishna, Pharm. Eng. 1992, 12, 48-51;
62. b) W. Ohtani, Y. Nawa, K. Takeshima, H. Kamuro, K. Kobayashi, T. Ohmura, Anal. Biochem. 1998, 256, 56-62.