Reaction: 5-O-(1-carboxyvinyl)-3-phosphoshikimate = chorismate + phosphate
For diagram click here and mechanism here.
Other name(s): 5-O-(1-carboxyvinyl)-3-phosphoshikimate phosphate-lyase
Systematic name: 5-O-(1-carboxyvinyl)-3-phosphoshikimate phosphate-lyase (chorismate-forming)
Comments: Requires FMN. The reaction goes via a radical mechanism that involves reduced FMN and its semiquinone (FMNH•). Shikimate is numbered so that the double-bond is between C-1 and C-2, but some earlier papers numbered the ring in the reverse direction.
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, PDB, CAS registry number: 9077-07-0
References:
1. Gaertner, F.H. and Cole, K.W. Properties of chorismate synthase in Neurospora crassa. J. Biol. Chem. 248 (1973) 4602-4609. [PMID: 4146266]
2. Morell, H., Clark, M.J., Knowles, P.F. and Sprinson, D.B. The enzymic synthesis of chorismic and prephenic acids from 3-enolpyruvylshikimic acid 5-phosphate. J. Biol. Chem. 242 (1967) 82-90. [PMID: 4289188]
3. Welch, G.R., Cole, K.W. and Gaertner, F.H. Chorismate synthase of Neurospora crassa: a flavoprotein. Arch. Biochem. Biophys. 165 (1974) 505-518. [PMID: 4155270]
4. Bornemann, S., Lowe, D.J. and Thorneley, R.N. The transient kinetics of Escherichia coli chorismate synthase: substrate consumption, product formation, phosphate dissociation, and characterization of a flavin intermediate. Biochemistry 35 (1996) 9907-9916. [PMID: 8703965]
5. Bornemann, S., Theoclitou, M.E., Brune, M., Webb, M.R., Thorneley, R.N. and Abell, C. A secondary β deuterium kinetic isotope effect in the chorismate synthase reaction. Bioorg. Chem. 28 (2000) 191-204. [PMID: 11034781]
6. Osborne, A., Thorneley, R.N., Abell, C. and Bornemann, S. Studies with substrate and cofactor analogues provide evidence for a radical mechanism in the chorismate synthase reaction. J. Biol. Chem. 275 (2000) 35825-35830. [PMID: 10956653]