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MetaCyc Pathway: salicylate biosynthesis I

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: salicylic acid biosynthesis

Superclasses: Biosynthesis Aromatic Compounds Biosynthesis
Biosynthesis Secondary Metabolites Biosynthesis Phenylpropanoid Derivatives Biosynthesis Benzenoids Biosynthesis Salicylate Biosynthesis

Some taxa known to possess this pathway include ? : Arabidopsis thaliana col , Catharanthus roseus , Cucumis sativus , Mycobacterium tuberculosis , Nicotiana tabacum , Pseudomonas aeruginosa , Yersinia enterocolitica , Yersinia pestis

Expected Taxonomic Range: Bacteria , Embryophyta

Summary:
Salicylate is an aromatic compound that is is common throughout the plant kingdom and is also found in some bacteria.

Several bacterial genera utilize salicylate as a building block for low-molecular-weight organic Fe3+ chelators (siderophores), such as yersiniabactin in Yersinia pestis and Yersinia enterocolitica, pyochelin in Pseudomonas aeruginosa, and mycobactin in Mycobacterium tuberculosis. In bacteria salicylate is derived from chorismate in two steps, via isochorismate, as described in this pathway.

Salicylate is also important in plants, where it induces flowering and is involved in resistance against pathogen infection through the systematic acquired resistance mechanism [Durrant04, Shah03]. While plants can make salicylate in more than one pathway (see salicylate biosynthesis II), genetic studies in Arabidopsis have shown that the bulk of salicylate is produced from chorismate [Wildermuth01].

Variants: salicylate biosynthesis II , salicylate glucosides biosynthesis I , salicylate glucosides biosynthesis II , salicylate glucosides biosynthesis III , salicylate glucosides biosynthesis IV

Credits:
Created 18-Dec-2009 by Caspi R , SRI International


References

Durrant04: Durrant WE, Dong X (2004). "Systemic acquired resistance." Annu Rev Phytopathol 42;185-209. PMID: 15283665

Kerbarh05: Kerbarh O, Ciulli A, Howard NI, Abell C (2005). "Salicylate biosynthesis: overexpression, purification, and characterization of Irp9, a bifunctional salicylate synthase from Yersinia enterocolitica." J Bacteriol 187(15);5061-6. PMID: 16030197

Shah03: Shah J (2003). "The salicylic acid loop in plant defense." Curr Opin Plant Biol 6(4);365-71. PMID: 12873532

Wildermuth01: Wildermuth MC, Dewdney J, Wu G, Ausubel FM (2001). "Isochorismate synthase is required to synthesize salicylic acid for plant defence." Nature 414(6863);562-5. PMID: 11734859

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

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

Dahm98: Dahm C, Muller R, Schulte G, Schmidt K, Leistner E (1998). "The role of isochorismate hydroxymutase genes entC and menF in enterobactin and menaquinone biosynthesis in Escherichia coli." Biochim Biophys Acta 1425(2);377-86. PMID: 9795253

Daruwala96: Daruwala R, Kwon O, Meganathan R, Hudspeth ME (1996). "A new isochorismate synthase specifically involved in menaquinone (vitamin K2) biosynthesis encoded by the menF gene." FEMS Microbiol Lett 1996;140(2-3);159-63. PMID: 8764478

Daruwala97: Daruwala R, Bhattacharyya DK, Kwon O, Meganathan R (1997). "Menaquinone (vitamin K2) biosynthesis: overexpression, purification, and characterization of a new isochorismate synthase from Escherichia coli." J Bacteriol 1997;179(10);3133-8. PMID: 9150206

Kolappan07: Kolappan S, Zwahlen J, Zhou R, Truglio JJ, Tonge PJ, Kisker C (2007). "Lysine 190 is the catalytic base in MenF, the menaquinone-specific isochorismate synthase from Escherichia coli: implications for an enzyme family." Biochemistry 46(4);946-53. PMID: 17240978

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Liu90: Liu J, Quinn N, Berchtold GA, Walsh CT (1990). "Overexpression, purification, and characterization of isochorismate synthase (EntC), the first enzyme involved in the biosynthesis of enterobactin from chorismate." Biochemistry 1990;29(6);1417-25. PMID: 2139795

Miller02b: Miller DA, Luo L, Hillson N, Keating TA, Walsh CT (2002). "Yersiniabactin synthetase: a four-protein assembly line producing the nonribosomal peptide/polyketide hybrid siderophore of Yersinia pestis." Chem Biol 9(3);333-44. PMID: 11927258

Ozenberger89: Ozenberger BA, Brickman TJ, McIntosh MA (1989). "Nucleotide sequence of Escherichia coli isochorismate synthetase gene entC and evolutionary relationship of isochorismate synthetase and other chorismate-utilizing enzymes." J Bacteriol 1989;171(2);775-83. PMID: 2536681

Rakin00: Rakin A, Schubert S, Guilvout I, Carniel E, Heesemann J (2000). "Local hopping of IS3 elements into the A+T-rich part of the high-pathogenicity island in Yersinia enterocolitica 1B, O:8." FEMS Microbiol Lett 182(2);225-9. PMID: 10620670

Rakin99: Rakin A, Noelting C, Schubert S, Heesemann J (1999). "Common and specific characteristics of the high-pathogenicity island of Yersinia enterocolitica." Infect Immun 67(10);5265-74. PMID: 10496905

Rowland96: Rowland BM, Taber HW (1996). "Duplicate isochorismate synthase genes of Bacillus subtilis: regulation and involvement in the biosyntheses of menaquinone and 2,3-dihydroxybenzoate." J Bacteriol 178(3);854-61. PMID: 8550523

Serino95: Serino L, Reimmann C, Baur H, Beyeler M, Visca P, Haas D (1995). "Structural genes for salicylate biosynthesis from chorismate in Pseudomonas aeruginosa." Mol Gen Genet 249(2);217-28. PMID: 7500944

Sridharan10: Sridharan S, Howard N, Kerbarh O, Blaszczyk M, Abell C, Blundell TL (2010). "Crystal structure of Escherichia coli enterobactin-specific isochorismate synthase (EntC) bound to its reaction product isochorismate: implications for the enzyme mechanism and differential activity of chorismate-utilizing enzymes." J Mol Biol 397(1);290-300. PMID: 20079748

Tummuru89: Tummuru MK, Brickman TJ, McIntosh MA (1989). "The in vitro conversion of chorismate to isochorismate catalyzed by the Escherichia coli entC gene product. Evidence that EntA does not contribute to isochorismate synthase activity." J Biol Chem 1989;264(34);20547-51. PMID: 2684979

vanTegelen99: van Tegelen LJ, Moreno PR, Croes AF, Verpoorte R, Wullems GJ (1999). "Purification and cDNA cloning of isochorismate synthase from elicited cell cultures of Catharanthus roseus." Plant Physiol 119(2);705-12. PMID: 9952467

vanTegelen99a: van Tegelen, Leon JP, Bongaerts, Roger JM, Croes, AntonF, Verpoorte, Robert, Wullems, George J (1999). "Isochorismate synthase isoforms from elicited cell cultures of Rubia tinctorum." Phytochemistry 51:263-269.

Wyckoff97: Wyckoff EE, Stoebner JA, Reed KE, Payne SM (1997). "Cloning of a Vibrio cholerae vibriobactin gene cluster: identification of genes required for early steps in siderophore biosynthesis." J Bacteriol 179(22);7055-62. PMID: 9371453

Young71a: Young IG, Langman L, Luke RK, Gibson F (1971). "Biosynthesis of the iron-transport compound enterochelin: mutants of Escherichia coli unable to synthesize 2,3-dihydroxybenzoate." J Bacteriol 106(1);51-7. PMID: 4928016


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, biocyc14.