Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

Escherichia coli K-12 substr. MG1655 Pathway: chorismate biosynthesis I

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Locations of Mapped Genes:

Genetic Regulation Schematic: ?

Synonyms: aromatic amino acid biosynthesis, shikimate pathway

Superclasses: Biosynthesis Aromatic Compounds Biosynthesis Chorismate Biosynthesis
Superpathways

Summary:
Chorismate is an intermediate in the synthesis of three amino acids: tyrosine, phenylalanine and tryptophan. In addition it is a precursor of folic acid, ubiquinone, menaquinone, and enterochelin. The first reaction in the chorismate pathway, also referred to as shikimate pathway, is catalyzed by three separate enzymes, each of which is subject to feedback inhibition by one of the three amino acids. However, even in the presence of all three amino acids, sufficient enzymatic activity is present to permit synthesis of the other four metabolites synthesized from chorismate because the enzyme subject to regulation by tryptophan cannot be inhibited more than 60 percent.

Review: Pittard, J. and J. Yang (2004) "Biosynthesis of Phenylalanine and Tyrosine." EcoSal 3.6.1.8 [ECOSAL]

Superpathways: superpathway of phenylalanine, tyrosine, and tryptophan biosynthesis , superpathway of chorismate metabolism

Subpathways: 3-dehydroquinate biosynthesis I , chorismate biosynthesis from 3-dehydroquinate

Credits:
Revised 09-May-2006 by Ingraham JL , UC Davis
Revised 04-Aug-2009 by Caspi R , SRI International


References

ECOSAL: "Escherichia coli and Salmonella: Cellular and Molecular Biology." Online edition.

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

AbdelMeguid85: Abdel-Meguid SS, Smith WW, Bild GS (1985). "Crystallization of 5-enolpyruvylshikimate 3-phosphate synthase from Escherichia coli." J Mol Biol 186(3);673. PMID: 3912512

Akowski97: Akowski JP, Bauerle R (1997). "Steady-state kinetics and inhibitor binding of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase (tryptophan sensitive) from Escherichia coli." Biochemistry 1997;36(50);15817-22. PMID: 9398312

Anderson88a: Anderson KS, Sikorski JA, Johnson KA (1988). "Evaluation of 5-enolpyruvoylshikimate-3-phosphate synthase substrate and inhibitor binding by stopped-flow and equilibrium fluorescence measurements." Biochemistry 1988;27(5);1604-10. PMID: 3284585

Anton88: Anton IA, Coggins JR (1988). "Sequencing and overexpression of the Escherichia coli aroE gene encoding shikimate dehydrogenase." Biochem J 1988;249(2);319-26. PMID: 3277621

Arifuzzaman06: Arifuzzaman M, Maeda M, Itoh A, Nishikata K, Takita C, Saito R, Ara T, Nakahigashi K, Huang HC, Hirai A, Tsuzuki K, Nakamura S, Altaf-Ul-Amin M, Oshima T, Baba T, Yamamoto N, Kawamura T, Ioka-Nakamichi T, Kitagawa M, Tomita M, Kanaya S, Wada C, Mori H (2006). "Large-scale identification of protein-protein interaction of Escherichia coli K-12." Genome Res 16(5);686-91. PMID: 16606699

Baasov89: Baasov T, Knowles JR (1989). "Is the first enzyme of the shikimate pathway, 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase (tyrosine sensitive), a copper metalloenzyme?." J Bacteriol 171(11);6155-60. PMID: 2572582

Benach03: Benach J, Lee I, Edstrom W, Kuzin AP, Chiang Y, Acton TB, Montelione GT, Hunt JF (2003). "The 2.3-A crystal structure of the shikimate 5-dehydrogenase orthologue YdiB from Escherichia coli suggests a novel catalytic environment for an NAD-dependent dehydrogenase." J Biol Chem 278(21);19176-82. PMID: 12624088

Bender89: Bender SL, Mehdi S, Knowles JR (1989). "Dehydroquinate synthase: the role of divalent metal cations and of nicotinamide adenine dinucleotide in catalysis." Biochemistry 28(19);7555-60. PMID: 2514789

Berlyn69: Berlyn MB, Giles NH (1969). "Organization of enzymes in the polyaromatic synthetic pathway: separability in bacteria." J Bacteriol 99(1);222-30. PMID: 4979440

Berti09: Berti PJ, Chindemi P (2009). "Catalytic residues and an electrostatic sandwich that promote enolpyruvyl shikimate 3-phosphate synthase (AroA) catalysis." Biochemistry 48(17);3699-707. PMID: 19271774

Bondinell71: Bondinell WE, Vnek J, Knowles PF, Sprecher M, Sprinson DB (1971). "On the mechanism of 5-enolpyruvylshikimate 3-phosphate synthetase." J Biol Chem 1971;246(20);6191-6. PMID: 4942558

Bornemann00: Bornemann S, Theoclitou ME, Brune M, Webb MR, Thorneley RN, Abell C (2000). "A Secondary beta Deuterium Kinetic Isotope Effect in the Chorismate Synthase Reaction." BIO-ORGANIC CHEMISTRY 28(4);191-204. PMID: 11034781

Bornemann02: Bornemann S (2002). "Flavoenzymes that catalyse reactions with no net redox change." Nat Prod Rep 19(6);761-72. PMID: 12521268

Bornemann95: Bornemann S, Balasubramanian S, Coggins JR, Abell C, Lowe DJ, Thorneley RN (1995). "Escherichia coli chorismate synthase: a deuterium kinetic-isotope effect under single-turnover and steady-state conditions shows that a flavin intermediate forms before the C-(6proR)-H bond is cleaved." Biochem J 305 ( Pt 3);707-10. PMID: 7848266

Bornemann95a: Bornemann S, Ramjee MK, Balasubramanian S, Abell C, Coggins JR, Lowe DJ, Thorneley RN (1995). "Escherichia coli chorismate synthase catalyzes the conversion of (6S)-6-fluoro-5-enolpyruvylshikimate-3-phosphate to 6-fluorochorismate. Implications for the enzyme mechanism and the antimicrobial action of (6S)-6-fluoroshikimate." J Biol Chem 270(39);22811-5. PMID: 7559411

Bornemann96: Bornemann S, Lowe DJ, Thorneley RN (1996). "The transient kinetics of Escherichia coli chorismate synthase: substrate consumption, product formation, phosphate dissociation, and characterization of a flavin intermediate." Biochemistry 35(30);9907-16. PMID: 8703965

Bornemann96a: Bornemann S, Lowe DJ, Thorneley RN (1996). "Escherichia coli chorismate synthase." Biochem Soc Trans 24(1);84-8. PMID: 8674765

BRENDA14: BRENDA team (2014). "Imported from BRENDA version existing on Aug 2014." http://www.brenda-enzymes.org.

Camakaris71: Camakaris J, Pittard J (1971). "Repression of 3-deoxy-D-arabinoheptulosonic acid-7-phosphate synthetase (trp) and enzymes of the tryptophan pathway in Escherichia coli K-12." J Bacteriol 1971;107(2);406-14. PMID: 4939760

Camakaris74: Camakaris J, Pittard J (1974). "Purification and properties of 3-deoxy-D-arabionheptulosonic acid-7-phosphate synthetase (trp) from Escherichia coli." J Bacteriol 1974;120(2);590-7. PMID: 4218228

Showing only 20 references. To show more, press the button "Show all references".


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, biocyc14.