Highly efficient and site-selective phosphane modification of proteins through hydrazone linkage: Development of artificial metalloenzymes

Angewandte Chemie - International Edition

Volumn 49, Issue 31, 2010, Pages 5315-5317

  Deuss, Peter J ^a   Popa, Gina ^a   Botting, Catherine H ^a   Laan, Wouter ^a   Kamer, Paul C J ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

Bioconjugation; Hydrazones; Metalloenzymes; Phosphanes; Rhodium

Indexed keywords

ARTIFICIAL METALLOENZYMES; BIO-CONJUGATION; HYDRAZONES; MALEIMIDES; METALLOENZYMES; PHOSPHANE LIGANDS; PHOSPHANES; SITE SELECTIVE;

ALDEHYDES; FUNCTIONAL GROUPS; RHODIUM;

ENZYMES;

ENZYME; HYDRAZONE DERIVATIVE; METALLOPROTEIN; PHOSPHINE; PHOSPHINE DERIVATIVE; PROTEIN;

ARTICLE; CHEMISTRY; METABOLISM;

ENZYMES; HYDRAZONES; METALLOPROTEINS; PHOSPHINES; PROTEINS;

EID: 77954849369     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002174     Document Type: Article

References (29)

1. P. W. N. M. van Leeuwen, Homogeneous Catalysis: Understanding the Art, Kluwer Academic Publishers, Dordrecht, 2004.
2. a) J. A. Gillespie, D. L. Dodds, P. C. J. Kamer, Dalton Trans. 2010, 39, 2751;
3. b) Phosphorus Ligands in Asymmetric Catalysis; Synthesis and Applications (Ed.: A. Borner), Wiley-VCH, Weinheim, 2008.
4. a) J. Steinreiber, T. R. Ward, Coord. Chem Rev. 2008, 252, 751;
5. b) T. Heinisch, T. R. Ward, Curr. Opin. Chem. Biol. 2010, 14, 184.
6. H. Yamaguchi, T. Hirano, H. Kiminami, D. Taura, A. Harada, Org. Biomol. Chem, 2006, 4, 3571.
7. a) M. E. Wilson, G. M. Whitesides, J. Am. Chem. Soc. 1978, 100, 306;
8. b) C.-C. Lin, C.-W. Lin, A. S. C. Chan, Tetrahedron: Asymmetry 1999, 10, 1887.
9. a) J. Pierron, C. Malan, M. Creus, J. Gradinaru, I. Hafner, A. Ivanova, A. Sardo, T. R. Ward, Angew. Chem. 2008, 120, 713;
10. Angew. Chem. Int. Ed. 2008, 47, 701;
11. b) G. Klein, N. Humbert, J. Gradinaru, A. Ivanova, F. Gilardoni, U. E. Rusbandi, T. R. Ward, Angew. Chem. 2005, 117, 7942;
12. Angew. Chem. Int. Ed. 2005, 44, 1764.
13. M. T. Reetz, J. J. P. Peyralans, A. Maichele, Y. Fu, M. Maywald, Chem. Commun. 2006, 4318.
14. M. T. Reetz, M. Rentzsch, A. Pletsch, M. Maywald, Chimia 2002, 56, 721.
15. A. M. Haapalainen, D. M. F. van Aalten, G. Merilaeinen, J. E. Jalonen, P. Pirilae, R. K. Wierenga, J. K. Hiltunen, T. Glumoff, J. Mol. Biol 2001, 313, 1127.
16. T. E. Meyer, E. Yakali, M. A. Cusanovich, G. Tollin, Biochemistry 1987, 26, 418.
17. G. E. O. Borgstahl, D. R. Williams, E. D. Getzoff, Biochemistry 1995, 34, 6278.
18. S. Anderson, V. Dragnea, S. Masuda, J. Ybe, K. Moffat, C. Bauer, Biochemistry 2005, 44, 7998.
19. J. S. Grinstead, S.-T. D. Hsu, W. Laan, A. M. J. J. Bonvin, K. J. Hellingwerf, R. Boelens, R. Kaptein, ChemBioChem 2006, 7, 187.
20. Bioconjugate Techniques, 2nd ed. (Ed.: G.T. Hermanson), Acadamic Press, San Diego, 2008.
21. a) R. R. Davies, M. D. Distefano, J. Am. Chem. Soc. 1997, 119, 11643;
22. b) M. T. Reetz, M. Rentzsch, A. Pletsch, A. Taglieber, F. Hollmann, R. J. G. Mondiere, N. Dickmann, B. Hoecker, S. Cerrone, M. C. Haeger, R. Sterner, ChemBioChem 2008, 9, 552.
23. W. Laan, B. K. Muñoz, R. den Heeten, P. C. J. Kamer, ChemBioChem 2010, DOI:10.1002/cbic.201000159.
24. Reference to this phenomenon can be found in references [4] and [14] as well as R. den Heeten, B. K. Muñoz, G. Popa, W. Laan and P. C. J. Kamer, Dalton Trans. 2010, DOI:10.1039/C0DT00239A.
25. E. Hedaya, S. Theodoropulos, Tetrahedron 1968, 24, 2241.
26. a) T. P. King, S. W. Zhao, T. Lam, Biochemistry 1986, 25, 5714;
27. b) A. Dirksen, P. E. Dawson, Bioconjugate Chem. 2008, 19, 2543.
28. K. K. Hii, S. D. Perera, B. L. Shaw, M. Thornton-Pett, J. Chem. Soc. Dalton Trans. 1992, 2361.
29. J. M. Chalker, C. S. C. Wood, B. G. Davis, J. Am. Chem. Soc. 2009, 131, 16346.