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Pathway Description
Enterobactin Biosynthesis
Escherichia coli
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2015-10-08
Last Updated: 2025-05-10
Enterobactin (also known as Enterochelin) is produced by enterobacteria such as Escherichia coli and Salmonella typhimurium. Under iron-deficient condtion, enterobactin can be synthesized and excreted into environment to bind Fe(III). Chorismate is the starting compound for enterobactin biosynthesis, and it can be obtained from chorismate biosynthesis pathway. Isochorismate synthase catalyzes chorismate to form isochorismate, and further breaking down to form (2S,3S)-2,3-dihydroxy-2,3-dihydrobenzoate and pyruvic acid by same synthase enzyme. (2S,3S)-2,3-dihydroxy-2,3-dihydrobenzoate is converted to 2,3-Dihydroxybenzoic acid by 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase. The later synthesis of enterobactin is catalyzed from 2,3-dihydroxybenzoate and L-serine.
References
Enterobactin Biosynthesis References
Gehring AM, Bradley KA, Walsh CT: Enterobactin biosynthesis in Escherichia coli: isochorismate lyase (EntB) is a bifunctional enzyme that is phosphopantetheinylated by EntD and then acylated by EntE using ATP and 2,3-dihydroxybenzoate. Biochemistry. 1997 Jul 15;36(28):8495-503. doi: 10.1021/bi970453p.
Pubmed: 9214294
Ozenberger BA, Brickman TJ, McIntosh MA: Nucleotide sequence of Escherichia coli isochorismate synthetase gene entC and evolutionary relationship of isochorismate synthetase and other chorismate-utilizing enzymes. J Bacteriol. 1989 Feb;171(2):775-83. doi: 10.1128/jb.171.2.775-783.1989.
Pubmed: 2536681
Kwon O, Hudspeth ME, Meganathan R: Anaerobic biosynthesis of enterobactin Escherichia coli: regulation of entC gene expression and evidence against its involvement in menaquinone (vitamin K2) biosynthesis. J Bacteriol. 1996 Jun;178(11):3252-9. doi: 10.1128/jb.178.11.3252-3259.1996.
Pubmed: 8655506
Dahm C, Muller R, Schulte G, Schmidt K, Leistner E: The role of isochorismate hydroxymutase genes entC and menF in enterobactin and menaquinone biosynthesis in Escherichia coli. Biochim Biophys Acta. 1998 Oct 23;1425(2):377-86. doi: 10.1016/s0304-4165(98)00089-0.
Pubmed: 9795253
Nahlik MS, Brickman TJ, Ozenberger BA, McIntosh MA: Nucleotide sequence and transcriptional organization of the Escherichia coli enterobactin biosynthesis cistrons entB and entA. J Bacteriol. 1989 Feb;171(2):784-90. doi: 10.1128/jb.171.2.784-790.1989.
Pubmed: 2521621
Rusnak F, Liu J, Quinn N, Berchtold GA, Walsh CT: Subcloning of the enterobactin biosynthetic gene entB: expression, purification, characterization, and substrate specificity of isochorismatase. Biochemistry. 1990 Feb 13;29(6):1425-35. doi: 10.1021/bi00458a013.
Pubmed: 2139796
Liu J, Duncan K, Walsh CT: Nucleotide sequence of a cluster of Escherichia coli enterobactin biosynthesis genes: identification of entA and purification of its product 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase. J Bacteriol. 1989 Feb;171(2):791-8. doi: 10.1128/jb.171.2.791-798.1989.
Pubmed: 2521622
Khalil S, Pawelek PD: Enzymatic adenylation of 2,3-dihydroxybenzoate is enhanced by a protein-protein interaction between Escherichia coli 2,3-dihydro-2,3-dihydroxybenzoate dehydrogenase (EntA) and 2,3-dihydroxybenzoate-AMP ligase (EntE). Biochemistry. 2011 Feb 1;50(4):533-45. doi: 10.1021/bi101558v. Epub 2010 Dec 31.
Pubmed: 21166461
Staab JF, Elkins MF, Earhart CF: Nucleotide sequence of the Escherichia coli entE gene. FEMS Microbiol Lett. 1989 May;50(1-2):15-9. doi: 10.1016/0378-1097(89)90450-3.
Pubmed: 2525505
Blattner FR, Plunkett G 3rd, Bloch CA, Perna NT, Burland V, Riley M, Collado-Vides J, Glasner JD, Rode CK, Mayhew GF, Gregor J, Davis NW, Kirkpatrick HA, Goeden MA, Rose DJ, Mau B, Shao Y: The complete genome sequence of Escherichia coli K-12. Science. 1997 Sep 5;277(5331):1453-62. doi: 10.1126/science.277.5331.1453.
Pubmed: 9278503
Hayashi K, Morooka N, Yamamoto Y, Fujita K, Isono K, Choi S, Ohtsubo E, Baba T, Wanner BL, Mori H, Horiuchi T: Highly accurate genome sequences of Escherichia coli K-12 strains MG1655 and W3110. Mol Syst Biol. 2006;2:2006.0007. doi: 10.1038/msb4100049. Epub 2006 Feb 21.
Pubmed: 16738553
Rusnak F, Sakaitani M, Drueckhammer D, Reichert J, Walsh CT: Biosynthesis of the Escherichia coli siderophore enterobactin: sequence of the entF gene, expression and purification of EntF, and analysis of covalent phosphopantetheine. Biochemistry. 1991 Mar 19;30(11):2916-27. doi: 10.1021/bi00225a027.
Pubmed: 1826089
Pettis GS, McIntosh MA: Molecular characterization of the Escherichia coli enterobactin cistron entF and coupled expression of entF and the fes gene. J Bacteriol. 1987 Sep;169(9):4154-62. doi: 10.1128/jb.169.9.4154-4162.1987.
Pubmed: 3040679
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