Generation, Characterization, and Tunable Reactivity of Organometallic Fragments Bound to a Protein Ligand

Journal of the American Chemical Society

Volumn 137, Issue 25, 2015, Pages 8261-8268

  Key, Hanna M ^a,b   Clark, Douglas S ^a,b   Hartwig, John F ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BINDING SITES; CARBON; CARBONIC ANHYDRASE; IRIDIUM; METAL COMPLEXES; METALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; PROTEINS; RHODIUM; SCAFFOLDS (BIOLOGY); ULTRAVIOLET VISIBLE SPECTROSCOPY;

COLORIMETRIC ASSAYS; GENETIC MANIPULATIONS; HUMAN CARBONIC ANHYDRASES; METAL BINDING SITES; ORGANO-METALLIC COMPLEXES; ORGANOMETALLIC REACTION; STOICHIOMETRIC REACTION; SYNTHETIC TRANSFORMATIONS;

LIGANDS;

CARBONATE DEHYDRATASE; IRIDIUM; LIGAND; ORGANOMETALLIC COMPOUND; RHODIUM; SCAFFOLD PROTEIN; PROTEIN BINDING;

ARTICLE; BINDING SITE; CHEMICAL BINDING; CHEMICAL REACTION; COLORIMETRY; GENETIC MANIPULATION; HUMAN; INFRARED SPECTROSCOPY; METAL BINDING; STOICHIOMETRY; ULTRAVIOLET SPECTROSCOPY; CHEMISTRY; METABOLISM;

CARBONIC ANHYDRASES; HUMANS; IRIDIUM; LIGANDS; ORGANOMETALLIC COMPOUNDS; PROTEIN BINDING; RHODIUM;

EID: 84934777140     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b04431     Document Type: Article

References (32)

1. Hartwig, J. F. Organotransition metal chemistry; 2010, University Science Books, Mill Valley, CA.
2. Andreini, C.; Bertini, I.; Cavallaro, G.; Holliday, G. L.; Thornton, J. M. J. Biol. Inorg. Chem. 2008, 8, 1205-1218
3. Reetz, M. T.; Peyralans, J. J.-P.; Maichele, A.; Fu, Y.; Maywald, M. Chem. Commun. 2006, 4318-4320
4. Wilson, M. E.; Whitesides, G. M. J. Am. Chem. Soc. 1978, 100, 306-307
5. Rosati, F.; Roelfes, G. ChemCatChem 2010, 2, 916-927
6. Lewis, J. C. ACS Catal. 2013, 3, 2954-2975
7. Carey, J. R.; Ma, S. K.; Pfister, T. D.; Garner, D. K.; Kim, H. K.; Abramite, J. A.; Wang, Z.; Guo, Z.; Lu, Y. J. Am. Chem. Soc. 2004, 126, 10812-10813
8. Dürrenberger, M.; Heinisch, T.; Wilson, Y. M.; Rossel, T.; Nogueira, E.; Knörr, L.; Mutschler, A.; Kersten, K.; Zimbron, M. J.; Pierron, J.; Schirmer, T.; Ward, T. R. Angew. Chem., Int. Ed. 2011, 50, 3026-3029
9. 1, T.; Ueno, T.; Yanase, M.; Fujii, H.; Watanabe, Y. Angew. Chem., Int. Ed. 2003, 42, 1005-1008
10. Ward, T. R. Acc. Chem. Res. 2011, 44, 47-57
11. Abe, S.; Hirata, K.; Ueno, T.; Morino, K.; Shimizu, N.; Yamamoto, M.; Takata, M.; Yashima, E.; Watanabe, Y. J. Am. Chem. Soc. 2009, 131, 6958-6960
12. Abe, S.; Niemeyer, J.; Abe, M.; Takezawa, Y.; Ueno, T.; Hikage, T.; Erker, G.; Watanabe, Y. J. Am. Chem. Soc. 2008, 130, 10512-10514
13. Abe, S.; Hikage, T.; Watanabe, Y.; Kitagawa, S.; Ueno, T. Inorg. Chem. 2010, 49, 6967-6973
14. Ueno, T.; Abe, M.; Hirata, K.; Abe, S.; Suzuki, M.; Shimizu, N.; Yamamoto, M.; Takata, M.; Watanabe, Y. J. Am. Chem. Soc. 2009, 131, 5094-5100
15. Okrasa, K.; Kazlauskas, R. J. Chem. - Eur. J. 2006, 12, 1587-1596
16. Jing, Q.; Kazlauskas, R. J. ChemCatChem 2010, 2, 953-957
17. Jing, Q.; Okrasa, K.; Kazlauskas, R. J. Chem. - Eur. J. 2009, 15, 1370-1376
18. Fernández Gacio, A.; Codina, A.; Fastrez, J.; Riant, O.; Soumillion, P. ChemBioChem 2006, 7, 1013-1016
19. Podtetenieff, J.; Taglieber, A.; Bill, E.; Reijerse, E. J.; Reetz, M. T. Angew. Chem., Int. Ed. 2010, 49, 5151-5155
20. Krishnamurthy, V. M.; Kaufman, G. K.; Urbach, G. K.; Gitlin, I.; Gudiksen, K. L.; Weibel, D. B.; Whitesides, G. M. Chem. Rev. 2008, 108, 946-1051
21. Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. 1994, 33, 497-526
22. Thorslund, A.; Lindskog, S. Eur. J. Biochem. 1967, 3, 117-123
23. Hakansson, K.; Wehnert, A.; Liljas, A. Acta Crystallogr., Sect. D 1994, 50, 93-100
24. Winn-Deen, E. S.; David, H.; Sigler, G.; Chavez, R. Clin. Chem. 1988, 34, 2005-2008
25. Plocke, D. J.; Levinthal, C.; Vallee, B. L. Biochemistry 1962, 1, 373-378
26. Wang, J.; Sheppard, G. S.; Lou, P.; Kawai, M.; Park, C.; Egan, D. A.; Schneider, A.; Bouska, J.; Lesniewski, R.; Henkin, J. Biochemistry 2003, 42, 5035-5042
27. Houchin, O. B. Clin. Chem. 1958, 4, 519-523
28. Ojima, I.; Vu, T.; Bonafoux, D. Organometallic complexes of rhodium. In Houben-Weyl, Methods of Molecular Transformations; Trost, B. M.; Lautens, M., Eds.; Thieme: Stuttgurt, 2001; Vol. 1, pp 531-616.
29. Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169-196
30. Although prior work (ref 11c) reported that dialysis can be used to eliminate excess rhodium from the protein surface (as determined by ICP-MS), we are unable to reproduce these results, in part because this publication does not describe the method for sample preparation. We found from a series of ICP-OES measurements that a high concentration of nitric acid and sufficient sample heating is necessary to detect all the Rh in protein-containing samples. Milder methods (without heating or with lower acid concentrations) reported for metal analysis of metalloproteins failed to detect all Rh in control samples (ref 20).
31. Shimahara, H.; Yoshida, T.; Shibata, Y.; Shimizu, M.; Kyogoku, Y.; Sakiyama, F.; Nakazawa, T.; Tate, S.-I.; Ohki, S.-Y.; Kato, T.; Moriyama, H.; Kishida, K.-I.; Tano, Y.; Ohkubo, T.; Kobayashi, Y. J. Biol. Chem. 2007, 282, 9646-9656
32. Robinson, N.; Waldron, K.; Tottey, S.; Bessant, C. Nature Protoc. Exch. 2008, 10.1038/nprot.2008.236