Isopenicillin N synthase mediates thiolate oxidation to sulfenate in a depsipeptide substrate analogue: Implications for oxygen binding and a link to nitrile hydratase?

Journal of the American Chemical Society

Volumn 130, Issue 31, 2008, Pages 10096-10102

  Ge, Wei ^a   Clifton, Ian J ^a   Stok, Jeanette E ^a,c   Adlington, Robert M ^a   Baldwin, Jack E ^a   Rutledge, Peter J ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF SYDNEY   (Australia)

^c CBio Limited   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; CHEMICAL OXYGEN DEMAND; CHLORINE COMPOUNDS; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; CYANIDES; ENZYME ACTIVITY; ESTERS; FOOD ADDITIVES; HEALTH; IRON COMPOUNDS; METALS; MINERALOGY; NONMETALS; ORGANIC COMPOUNDS; OXIDATION; OXYGEN; POWDERS;

ACTIVE SITES; CO SUBSTRATES; D-VALINE; ETHYL ESTERS; GROWN CRYSTALS; IRON COMPLEXES; ISOPENICILLIN N SYNTHASE; L-CYSTEINE; MECHANISTIC PROBES; NITRILE HYDRATASE; NITRILE HYDRATASES; NONHEME IRON; OXIDATIVE CYCLIZATION; OXYGEN BINDING; OXYGEN GASES; REACTION PATHWAYS; THIOLATE; THIOLATES; TRI PEPTIDES; WATER LIGANDS;

ENZYMES;

BETA LACTAM; DEPSIPEPTIDE; IRON; ISOPENICILLIN N SYNTHETASE; NITRILE HYDRATASE; OXIDOREDUCTASE; SULFENIC ACID DERIVATIVE; SULFINIC ACID DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYCLIZATION; ENZYME ACTIVITY; ENZYME METABOLISM; HYPERBARIC OXYGEN; METAL BINDING; OXIDATION KINETICS; OXYGEN AFFINITY; PROTEIN PROCESSING; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

CYCLIZATION; DEPSIPEPTIDES; HYDRO-LYASES; OXIDATION-REDUCTION; OXIDOREDUCTASES; OXYGEN; SULFENIC ACIDS; SULFHYDRYL COMPOUNDS;

EID: 48749101192     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8005397     Document Type: Article

References (42)

1. Baldwin, J. E. In Special Publication No. 52; Brown, A. G., Roberts, S. M., Eds.; The Royal Society of Chemistry: London, 1985; pp 62-85.
2. Baldwin, J. E.; Schofield, C. J. In The Chemistry of β-Lactams; Page, M. I., Ed.; Blackie: Glasgow, 1992; pp 1-78.
3. Baldwin, J. E.; Bradley, M. Chem. Rev. 1990, 90, 1079-1088.
4. Roach, P. L.; Clifton, I. J.; Fulop, V.; Harlos, K.; Barton, G. J.; Hajdu, J.; Andersson, I.; Schofield, C. J.; Baldwin, J. E. Nature 1995, 375, 700-704.
5. Roach, P. L.; Clifton, I. J.; Hensgens, C. M. H.; Shibata, N.; Schofield, C. J.; Hadju, J.; Baldwin, J. E. Nature 1997, 387, 827-830.
6. Burzlaff, N. I.; Rutledge, P. J.; Clifton, I. J.; Hensgens, C. M. H.; Pickford, M.; Adlington, R. M.; Roach, P. L.; Baldwin, J. E. Nature 1999, 401, 721-724.
7. Rutledge, P. J.; Burzlaff, N. I.; Elkins, J. M.; Pickford, M.; Baldwin J. E.; Roach, P. L. Anal. Biochem. 2002, 308, 265-268.
8. Ogle, J. M.; Clifton, I. J.; Rutledge, P. J.; Elkins, J. M.; Burzlaff. N. I.; Adlington, R. M.; Roach, P. L.; Baldwin, J. E. Chem. Biol. 2001, 8, 1231-1237.
9. Elkins, J. M.; Rutledge, P. J.; Burzlaff, N. I.; Clifton, I. J.; Adlington, R. M.; Roach, P. L.; Baldwin, J. E. Org. Biomol. Chem. 2003, 1, 1455-1460.
10. Long, A. J.; Clifton, I. J.; Roach, P. L.; Baldwin, J. E.; Schofield, C. J.; Rutledge, P. J. Biochem. J. 2003, 372, 687-693.
11. Grummitt, A. R.; Rutledge, P. J.; Clifton, I. J.; Baldwin, J. E. Biochem. J. 2004, 382, 659-666.
12. Long, A. J.; Clifton, I. J.; Roach, P. L.; Baldwin, J. E.; Rutledge, P. J.; Schofield, C. J. Biochemistry 2005, 44, 6619-6628.
13. Howard-Jones, A. R.; Rutledge, P. J.; Clifton, I. J.; Adlington, R. M.; Baldwin, J. E. Biochem. Biophys. Res. Commun. 2005, 336, 702-708.
14. Daruzzaman, A.; Clifton, I. J.; Adlington, R. M.; Baldwin, J. E.; Rutledge, P. J. ChemBioChem 2006, 7, 351-358.
15. Howard-Jones, A. R.; Elkins, J. M.; Clifton, I. J.; Roach, P. L.; Adlington, R. M.; Baldwin, J. E.; Rutledge, P. J. Biochemistry 2007, 46, 4755-4762.
16. Stewart, A. C.; Clifton, I. J.; Adlington, R. M.; Baldwin, J. E.; Rutledge, P. J. ChemBioChem 2007, 8, 2003-2007.
17. Kung, I.; Schweitzer, D.; Shearer, J.; Taylor, W. D.; Jackson, H. L.: Lovell, S.; Kovacs, J. A. J. Am. Chem. Soc. 2000, 122, 8299-8300.
18. Cornman, C. R.; Stauffer, T. C.; Boyle, P. D. J. Am. Chem. Soc. 1997, 119, 5986-5987.
19. Zhang, Z.; Ren, J. S.; Stammers, D. K.; Baldwin, J. E.; Harlos, K.; Schofield, C. J. Nat. Struct. Biol. 1999, 7, 127-133.
20. Prescott, A. G.; Lloyd, M. D. Nat. Prod. Rep. 2000, 17, 367-383.
21. Clifton, I. J.; Hsueh, L. C.; Baldwin, J. E.; Harlos, K.; Schofield, C. J. Eur. J. Biochem. 2001, 268, 6625-6636.
22. Ryle, M. J.; Hausinger, R. P. Curr. Opin. Chem. Biol. 2002, 6, 193-201.
23. Hausinger, R. P. Crit. Rev. Biochem. Mol. Biol. 2004, 39, 21-68.
24. Costas, M.; Mehn, M. P.; Jensen, M. P.; Que, L. Chem. Rev. 2004, 104, 939-986.
25. Koehntop, K. D.; Emerson, J. P.; Que, L. J. Biol. Inorg. Chem. 2005, 10, 87-93.
26. Huang, W. J.; Jia, J.; Cummings, J.; Nelson, M.; Schneider, G.; Lindqvist, Y. Structure 1997, 5, 691-699.
27. Endo, I.; Nojiri, M.; Tsujimura, M.; Nakasako, M.; Nagashima, S.; Yohda, M.; Odaka, M. J. Inorg. Biochem. 2001, 83, 247-253.
28. Katayama, Y.; Hashimoto, K.; Nakayama, H.; Mino, H.; Nojiri, M.; Ono, T.; Nyunoya, H.; Yohda, M.; Takio, K.; Odaka, M. J. Am. Chem. Soc. 2006, 128, 728-729.
29. Murakami, T.; Nojiri, M.; Nakayama, H.; Odaka, M.; Yohda, M.; Dohmae, N.; Takio, K.; Nagamune, T.; Endo, I. Protein Sci. 2000, 9, 1024-1030.
30. Baldwin, J. E.; Herchen, S. R.; Johnson, B. L.; Jung, M.; Usher, J. J.; Wan, T. J. Chem. Soc., Perkin Trans. 1 1981, 2253-2257.
31. Prilezhaev, N. Ber. Deut. Chem. Ges. 1910, 42, 4811-4815.
32. Hagen, T. J. In Name Reactions for Functional Group Transformations; Li, J. J., Corey, E. J., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ, 2007; pp 274-281.
33. Mitsunobu, O. Synthesis-Stuttgart 1981, 1-28.
34. Bodanzky, M.; Bodanzky, A. In Reactivity and Structure Concepts in Organic Chemistry; Hafner, K., Rees, C. W., Trost, B. M., Lehn, J. M., Schleyer, P. v. R., Zahruchik, R., Eds.; Springer-Verlag: Berlin, 1984; Vol. 21, pp 172-173.
35. Roach, P. L.; Clifton, I. J.; Hensgens, C. M. H.; Shibata, N.; Long, A. J.; Strange, R. W.; Hasnain, S. S.; Schofield, C. J.; Baldwin, J. E.; Hajdu, J. Eur. J. Biochem. 1996, 242, 736-740.
36. Leslie, A. G. W. Acta Crystallogr. D 1999, 55, 1696-1702.
37. Collaborative Computational Project Number 4. Acta Crystallogr., D, 1994, 50, 760-763.
38. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Acta Crystallogr., Sect. D 1997, 53, 240-255.
39. Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjelgaard, M. Acta Crystallogr., A 1991, 47, 110-119.
40. Kraulis, P. J. J. Appl. Crystallogr. 1991, 24, 946-950.
41. Esnouf, R. M. Acta Crystallogr., D 1999, 55, 938-940.
42. Merritt, E. A.; Bacon, D. J. Methods Enzymol. 1997, 277, 505-524.