Design and synthesis of a novel triptycene-based ligand for modeling carboxylate-bridged diiron enzyme active sites

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5052-5055

  Li, Yang ^a   Cao, Rui ^a   Lippard, Stephen J ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE; CARBOXYLIC ACID; IRON; LIGAND; METHANE MONOOXYGENASE; OXYGENASE; TRIPTYCENE;

ARTICLE; CHEMISTRY; ENZYME ACTIVE SITE; METABOLISM; X RAY CRYSTALLOGRAPHY;

ANTHRACENES; CARBOXYLIC ACIDS; CATALYTIC DOMAIN; CRYSTALLOGRAPHY, X-RAY; IRON; LIGANDS; OXYGENASES;

EID: 80054756119     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201882v     Document Type: Article

References (30)

1. Feig, A. L.; Lippard, S. J. Chem. Rev. 1994, 94, 759-805.
2. Wallar, B. J.; Lipscomb, J. D. Chem. Rev. 1996, 96, 2625-2657.
3. Kurtz, D. M., Jr. J. Biol. Inorg. Chem. 1997, 2, 159-167.
4. Solomon, E. I.; Brunold, T. C.; Davis, M. I.; Kemsley, J. N.; Lee, S.-K.; Lehnert, N.; Neese, F.; Skulan, A. J.; Yang, Y.-S.; Zhou, J. Chem. Rev. 2000, 100, 235-349.
5. Merkx, M.; Kopp, D. A.; Sazinsky, M. H.; Blazyk, J. L.;Müller, J.; Lippard, S. J. Angew. Chem., Int. Ed. 2001, 40, 2782-2807.
6. Cafaro, V.; Scognamiglio, R.; Viggiani, A.; Izzo, V.; Passaro, I.; Notomista, E.; Dal Piaz, F.; Amoresano, A.; Casbarra, A.; Pucci, P.; Di Donato, A. Eur. J. Biochem. 2002, 269, 5689-5699.
7. Cafaro, V.; Izzo, V.; Scognamiglio, R.; Notomista, E.; Capasso, P.; Casbarra, A.; Pucci, P.; Di Donato, A. Appl. Environ. Microbiol. 2004, 70, 2211-2219.
8. Cadieux, E.; Vrajmasu, V.; Achim, C.; Powlowski, J.;Münck, E. Biochemistry 2002, 41, 10680-10691.
9. Gallagher, S. C.; Cammack, R.; Dalton,H. Eur. J. Biochem. 1997, 247, 635-641.
10. Bollinger, J. M., Jr.; Edmondson, D. E.; Huynh, B. H.; Filley, J.; Norton, J. R.; Stubbe, J. Science 1991, 253, 292-298.
11. Logan, D. T.; Su, X.-D.; Åberg, A.; Regnström, K.; Hajdu, J.; Eklund, H.; Nordlund, P. Structure 1996, 4, 1053-1064.
12. Lindqvist, Y.; Huang, W.; Schneider, G.; Shanklin, J. EMBO J. 1996, 15, 4081-4092.
13. Broadwater, J. A.; Ai, J.; Loehr, T. M.; Sanders-Loehr, J.; Fox, B. G. Biochemistry 1998, 37, 14664-14671.
14. Åberg, A.; Nordlund, P.; Eklund, H. Nature 1993, 361, 276-278.
15. Sazinsky, M. H.; Merkx, M.; Cadieux, E.; Tang, S.; Lippard, S. J. Biochemistry 2004, 43, 16263-16276.
16. Que, L., Jr. J. Chem. Soc., Dalton Trans. 1997, 3933-3940.
17. Fontecave, M.;Ménage, S.; Duboc-Toia, C. Coord. Chem. Rev. 1998, 178-180, 1555-1572.
18. Tshuva, E. Y.; Lippard, S. J. Chem. Rev. 2004, 104, 987-1011.
19. Que, L., Jr.; Tolman, W. B. Nature 2008, 455, 333-340.
20. Friedle, S.; Reisner, E.; Lippard, S. J. Chem. Soc. Rev. 2010, 39, 2768-2779.
21. Do, L. H.; Lippard, S. J. J. Inorg. Biochem. 2011, accepted for publication.
22. Kuzelka, J.; Farrell, J. R.; Lippard, S. J. Inorg. Chem. 2003, 42, 8652-8662.
23. Kodanko, J. J.; Xu, D.; Song, D.; Lippard, S. J. J. Am. Chem. Soc. 2005, 127, 16004-16005.
24. Friedle, S.; Kodanko, J. J.; Morys, A. J.; Hayashi, T.; Moënne- Loccoz, P.; Lippard, S. J. J. Am. Chem. Soc. 2009, 131, 14508-14520.
25. Do, L. H.; Lippard, S. J. J. Am. Chem. Soc. 2011, 133, 10568-10581.
26. Bartlett, P. D.; Ryan, M. J.; Cohen, S. G. J. Am. Chem. Soc. 1942, 64, 2649-2653.
27. Zhao, L.; Li, Z.; Wirth, T. Chem. Lett. 2010, 39, 658-667.
28. Ishii, H.; Ishikawa, T.; Takeda, S.; Ueki, S.; Suzuki, M. Chem. Pharm. Bull. 1992, 40, 1148-1153.
29. Dalcanale, E.; Montanari, F. J. Org. Chem. 1986, 51, 567-569.
30. Note: the details of this complex as well as its reactivity with molecular oxygen will be reported in a subsequent paper.