Isoprenoid biosynthesis: Ferraoxetane or allyl anion mechanism for IspH catalysis?

Angewandte Chemie - International Edition

Volumn 52, Issue 25, 2013, Pages 6522-6525

  Li, Jikun ^b   Wang, Ke ^a   Smirnova, Tatyana I ^c   Khade, Rahul L ^d   Zhang, Yong ^d   Oldfield, Eric ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c NORTH CAROLINA STATE UNIVERSITY   (United States)

^d Stevens Institute of Technology   (United States)

Author keywords

biosynthesis; enzyme catalysis; iron sulfur cluster; metalloproteins; terpenes

Indexed keywords

CATALYTIC MECHANISMS; DIPHOSPHATES; ENZYME CATALYSIS; HYSCORE; IRON-SULFUR CLUSTERS; ISOPENTENYL DIPHOSPHATE; ISOPRENOID BIOSYNTHESIS; METALLO-PROTEINS;

BIOCHEMISTRY; BIOSYNTHESIS; ENZYMES; PROTEINS; QUANTUM CHEMISTRY; TERPENES;

CATALYSIS;

ANION; FERRIC ION; PROTEIN; TERPENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; METABOLISM;

ANIONS; CATALYSIS; FERRIC COMPOUNDS; MODELS, MOLECULAR; PROTEINS; TERPENES;

EID: 84878923624     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201302343     Document Type: Article

References (27)

1. J. Buckingham, Dictionary of Natural Products on DVD, CRC, Boca Raton, 2011.
2. E. Oldfield, F.-Y. Lin, Angew. Chem. 2012, 124, 1150-1163
3. Angew. Chem. Int. Ed. 2012, 51, 1124-1137.
4. M. Wolff, M. Seemann, B. Tse Sum Bui, Y. Frapart, D. Tritsch, A. Garcia Estrabot, M. Rodríguez-Concepciõn, A. Boronat, A. Marquet, M. Rohmer, FEBS Lett. 2003, 541, 115-120.
5. W. Wang, K. Wang, Y.-L. Liu, J.-H. No, J. Li, M. J. Nilges, E. Oldfield, Proc. Natl. Acad. Sci. USA 2010, 107, 4522-4527.
6. W. Wang, K. Wang, I. Span, J. Jauch, A. Bacher, M. Groll, E. Oldfield, J. Am. Chem. Soc. 2012, 134, 11225-11234.
7. W. Xu, N. S. Lees, D. Hall, D. Welideniya, B. M. Hoffman, E. C. Duin, Biochemistry 2012, 51, 4835-4849.
8. W. Wang, J. Li, K. Wang, C. Huang, Y. Zhang, E. Oldfield, Proc. Natl. Acad. Sci. USA 2010, 107, 11189-11193.
9. W. Wang, K. Wang, J. Li, S. Nellutla, T. I. Smirnova, E. Oldfield, J. Am. Chem. Soc. 2011, 133, 8400-8403.
10. W. Xu, N. S. Lees, D. Adedeji, J. Wiesner, H. Jomaa, B. M. Hoffman, E. C. Duin, J. Am. Chem. Soc. 2010, 132, 14509-14520.
11. I. Span, T. Gräwert, A. Bacher, W. Eisenreich, M. Groll, J. Mol. Biol. 2012, 416, 1-9.
12. C. A. Citron, N. L. Brock, P. Rabe, J. S. Dickschat, Angew. Chem. 2012, 124, 4129-4133
13. Angew. Chem. Int. Ed. 2012, 51, 4053-4057.
14. P. Höfer, A. Grupp, H. Nebenführ, M. Mehring, Chem. Phys. Lett. 1986, 132, 279-282.
15. E. R. Davies, Phys. Lett. A 1974, 47, 1-2.
16. M. C. Kennedy, M. Werst, J. Telser, M. H. Emptage, H. Beinert, B. M. Hoffman, Proc. Natl. Acad. Sci. USA 1987, 84, 8854-8858.
17. M. M. Werst, M. C. Kennedy, H. Beinert, B. M. Hoffman, Biochemistry 1990, 29, 10526-10532.
18. J. Telser, M. H. Emptage, H. Merkle, M. C. Kennedy, H. Beinert, B. M. Hoffman, J. Biol. Chem. 1986, 261, 4840-4846.
19. S. Stoll, A. Schweiger, J. Magn. Reson. 2006, 178, 42-55.
20. T. Gräwert, I. Span, W. Eisenreich, F. Rohdich, J. Eppinger, A. Bacher, M. Groll, Proc. Natl. Acad. Sci. USA 2010, 107, 1077-1081.
21. T. Gräwert, I. Span, A. Bacher, M. Groll, Angew. Chem. 2010, 122, 8984-8991
22. Angew. Chem. Int. Ed. 2010, 49, 8802-8809.
23. C. J. Walsby, W. Hong, W. E. Broderick, J. Cheek, D. Ortillo, J. B. Broderick, B. M. Hoffman, J. Am. Chem. Soc. 2002, 124, 3143-3151.
24. Y. Zhang, E. Oldfield, J. Am. Chem. Soc. 2004, 126, 4470-4471.
25. K. Wang, W. Wang, J.-H. No, Y. Zhang, Y. Zhang, E. Oldfield, J. Am. Chem. Soc. 2010, 132, 6719-6727.
26. Y.-L. Liu, F. Guerra, K. Wang, W. Wang, J. Li, C. Huang, W. Zhu, K. Houlihan, Z. Li, Y. Zhang, S. K. Nair, E. Oldfield, Proc. Natl. Acad. Sci. USA 2012, 109, 8558-8563.
27. M. J. Frisch et al, Gaussian 09 Revision B.01, Gaussian, Inc., Wallingford, CT, 2010.