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Pathway Description
Biosynthesis of Siderophore Group Nonribosomal Peptides
Escherichia coli O127:H6 str. E2348/69
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2024-12-10
Last Updated: 2024-12-10
2,3-Dihydroxybenzoate is created from chorismate through isochorismate and 2,3-dihydroxy-2,3-dihydrobenzoate. The biosynthesis of 2,3-dihydroxybenzoate starts from chorismate being converted into isochorismate through isochorismate synthase entC. The N-terminal isochorismate lyase domain of EntB adds hydrogen to the pyruvate group of isochorismate to create 2,3-dihydro-2,3-dihydroxybenzoate. this latter compound to 2,3-dihydroxybenzoate is then converted by the catalyzation of EntA dehydrogenase. This compound then interacts with L-serine and ATP through the enterobactin synthase protein complex resulting in the production of enterobactin. Enterobactin is exported into the periplasmic space through the enterobactin exporter entS. Enterobactin is then exported into the environment through the outer membrane protein TolC. In the environment, enterobactin reacts with iron to produce ferric enterobactin. It is then imported into the periplasmic space through a ferric enterobactin outer membrane transport complex. Ferric enterobactin continues it's journey and enters the cytoplasm via a ferric enterobactin ABC transporter. Once inside the cytoplasm, ferric enterobactin spontaneously releases the iron ion from the enterobactin. Alternatively, it can react with water through an enterochelin esterase resulting in the release of 2,3-dihydroxybenzoylserine, Fe3+, and hydrogen ions.
References
Biosynthesis of Siderophore Group Nonribosomal Peptides References
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
Pettis GS, Brickman TJ, McIntosh MA: Transcriptional mapping and nucleotide sequence of the Escherichia coli fepA-fes enterobactin region. Identification of a unique iron-regulated bidirectional promoter. J Biol Chem. 1988 Dec 15;263(35):18857-63.
Pubmed: 2974033
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
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
Coderre PE, Earhart CF: The entD gene of the Escherichia coli K12 enterobactin gene cluster. J Gen Microbiol. 1989 Nov;135(11):3043-55. doi: 10.1099/00221287-136-8-1667.
Pubmed: 2533240
Armstrong SK, Pettis GS, Forrester LJ, McIntosh MA: The Escherichia coli enterobactin biosynthesis gene, entD: nucleotide sequence and membrane localization of its protein product. Mol Microbiol. 1989 Jun;3(6):757-66. doi: 10.1111/j.1365-2958.1989.tb00224.x.
Pubmed: 2526281
Oshima T, Aiba H, Baba T, Fujita K, Hayashi K, Honjo A, Ikemoto K, Inada T, Itoh T, Kajihara M, Kanai K, Kashimoto K, Kimura S, Kitagawa M, Makino K, Masuda S, Miki T, Mizobuchi K, Mori H, Motomura K, Nakamura Y, Nashimoto H, Nishio Y, Saito N, Horiuchi T, et al.: A 718-kb DNA sequence of the Escherichia coli K-12 genome corresponding to the 12.7-28.0 min region on the linkage map. DNA Res. 1996 Jun 30;3(3):137-55. doi: 10.1093/dnares/3.3.137.
Pubmed: 8905232
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
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
This pathway was propagated using PathWhiz -
Pon, A. et al. Pathways with PathWhiz (2015) Nucleic Acids Res. 43(Web Server issue): W552–W559.
Propagated from SMP0000783
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