Isochorismate synthase
| Isochorismate synthase | |||||||||
|---|---|---|---|---|---|---|---|---|---|
 Ishochorismate Synthase cartoon view (2 subunits) | |||||||||
| Identifiers | |||||||||
| EC number | 5.4.4.2 | ||||||||
| CAS number | 37318-53-9 | ||||||||
| Databases | |||||||||
| IntEnz | IntEnz view | ||||||||
| BRENDA | BRENDA entry | ||||||||
| ExPASy | NiceZyme view | ||||||||
| KEGG | KEGG entry | ||||||||
| MetaCyc | metabolic pathway | ||||||||
| PRIAM | profile | ||||||||
| PDB structures | RCSB PDB PDBe PDBsum | ||||||||
| |||||||||
Isochorismate synthase (MenF) (EC number 5.4.4.2) is involved in the biosynthesis of vitamin K in Escherichia coli. This enzyme catalyzes the first step in the biosynthesis of menaquinone (vitamin K).[1]
Reaction
Isochorismate synthase is an enzyme that catalyzes the irreversible reaction:
Chorismate→ Isochorismate
The only subrate of this reaction is chorismate, and the product is isochorismate. Isochorismate synthase is most active at 37℃ and at a pH between 7.5-8. Isochorismate synthase requires Mg2+. The concentration of Mg2+ may range from 100μM-1mM.[1] Inhibitors of isochorismate synthase include:
- (4R,5R)-4-hydroxy-5-(1-carboxyvinyloxy)-cyclohex-1-ene carboxylate
- (4R,5R)-4-hydroxy-5-carboxymethoxy-cyclohex-1-enecarboxylate
- (4R,5R)-5-(2-carboxy-allyloxy)-4-hydroxy-cyclohex-1-enecarboxylate
- (4R,5R,6S)-6-ammonio-5-[(1-carboxylatoethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylate
- (4R,5R,7R)-5-(1-carboxy-ethoxy)-4-hydroxy-cyclohex-1-enecarboxylate
- (4R,5R,7S)-5-(1-carboxy-ethoxy)-4-hydroxy-cyclohex-1-enecarboxylate
- (4R,5S,6S)-4-ammonio-5-[(1-carboxylatoethenyl)oxy]-6-hydroxycyclohex-1-ene-1-carboxylate
- (4R,5S,6S)-5-[(1-carboxylatoethenyl)oxy]-4,6-dihydroxycyclohex-1-ene-1-carboxylate[2]
- Cu2+
- Hg2+
- K+
- Mg2+ at concentrations above 1mM
- NEM
Nomenclature
Isochorismate synthase, or MenF, belongs to the isomerase enzyme family. More specifically it is classified as an intermolecular transferase because it transfers the hydroxy group of chorismate between carbons.[3] The systematic name of this enzyme is isochorismate hydroxymutase, and the common name is isochorismate synthase. Other names for this enzyme include:
- Isochorismate mutase
- Menaquinone-specific isochorismate synthase
- MenF
Vitamin K
Vitamin K is a quinone, which means it is a ring compound that participates in redox reactions. These redox reactions take place in various organisms ranging from plants where electrons are transferred during photosynthesis, humans where electrons are transferred to modify certain types of proteins, and even in bacteria where electrons are transferred during anaerobic respiration.[4]
Pathways
MenF is a gene that codes for the isochorismate synthase found in the menaquinone pathway in Escherichia coli, not to be mistaken for the entC gene that codes for the isochorismate synthase found in the enterobacter pathway in Escherichia coli.[1] Isochorismate synthase has several other homologs that are found in other organisms. These include:
| Enzyme Genes/Enzyme Names | Organisms |
|---|---|
| ICS | Arabidopsis thaliana
Cyanidium caldarium Glycime max Nicotiana benthamiana Populus fremontil Populus angustifolia Populous tremuloides |
| ICS1 | Arabidopsis thaliana |
| ICS1 gene product | Arabidopsis thaliana
Cyanidium caldarium |
| ICS2 | Arabidopsis thaliana |
| Isochorismate synthase | Arabidopsis thaliana
Cyanidium caldarium Glycine max |
| Isochorismate synthase 1 | Arapidopsis thaliana |
| Mbtl | Mycobacterium tuberculosis |
| PchA | Pseudomonas aeruginosa |
References
- 1 2 3 Daruwala, R; Bhattacharyya, D K; Kwon, O; Meganathan, R (May 1997). "Menaquinone (vitamin K2) biosynthesis: overexpression, purification, and characterization of a new isochorismate synthase from Escherichia coli.". Journal of Microbiology 179: 3133–3138. Retrieved 30 November 2014.
- ↑ Payne, RJ; Bulloch, EM; Toscano, MM; Jones, MA; Kerbarh, O; Abell, C (2 April 2009). "Synthesis and evaluation of 2,5-dihydrochorismate analogues as inhibitors of the chorismate-utilising enzyme.". Organic and Biomolecular Chemistry (11): 2421–2429. doi:10.1039/B901694E. PMID 19462053. Retrieved 30 November 2014.
- ↑ "EC 5.4.4.2". IUBMB. Retrieved 30 November 2014.
- ↑ van Oostende, C; Wildhalm, JR; Furt, F; Ducluzeau, AL; Basset, GJC (2011). "Phylloquinone (Vitamin K2): function,enzymes and genes". Advances in Botanical Research: 229–61.
| ||||||||||||||
| ||||||||||||||||||