Isochorismate synthase

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Isochorismate synthase
Isochorismate Synthase.png
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) catalyzes the first step in the biosynthesis of vitamin K (menaquinone) in Escherichia coli.[1]

Reaction[edit]

Isochorismate synthase is an enzyme that catalyzes the irreversible conversion of chorismate to isochorismate:

Isochorismate Synthase Rxn.png

Isochorismate synthase is most active at 37 °C and at a pH between 7.5 and 8. It requires Mg2+ as a cofactor, in a concentration between 100 μM and 1 mM.[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 1 mM
  • NEM[clarification needed]

Nomenclature[edit]

Isochorismate synthase, or MenF, belongs to the isomerase enzyme family. More specifically it is classified as an intramolecular 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[edit]

Vitamin K contains a quinone ring that participates in redox reactions. These reactions take place in various organisms such as plants, where electrons are transferred during photosynthesis, humans, where electrons are transferred to modify certain types of proteins, and bacteria, where electrons are transferred during anaerobic respiration.[4]

Pathways[edit]

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
  • Glycine max
  • Nicotiana benthamiana
  • Populus fremontil
  • Populus angustifolia
  • Populus 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[edit]

  1. ^ a b c 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. 
  2. ^ 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. 
  3. ^ "EC 5.4.4.2". IUBMB. Retrieved 30 November 2014. 
  4. ^ 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.