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Pathway Description
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis
Escherichia coli
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2015-06-30
Last Updated: 2025-05-08
The biosynthesis of a enterobacterial common antigen can begin with a di-trans,octa-cis-undecaprenyl phosphate interacts with a Uridine diphosphate-N-acetylglucosamine through undecaprenyl-phosphate α-N-acetylglucosaminyl transferase resulting in a N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol and a Uridine 5'-monophosphate. The N-acetyl-α-D-glucosaminyl-diphospho-ditrans,octacis-undecaprenol then reacts with an UDP-ManNAcA from the Amino sugar and nucleotide sugar metabolism pathway. This reaction is metabolized by a UDP-N-acetyl-D-mannosaminuronic acid transferase resulting in a uridine 5' diphosphate, a hydrogen ion and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. Glucose 1 phosphate can be metabolize by interacting with a hydrogen ion and a thymidine 5-triphosphate by either reacting with a dTDP-glucose pyrophosphorylase or a dTDP-glucose pyrophosphorylase 2 resulting in the release of a pyrophosphate and a dTDP-D-glucose. The latter compound is then dehydrated through an dTDP-glucose 4,6-dehydratase 2 resulting in water and dTDP-4-dehydro-6-deoxy-D-glucose. The latter compound interacts with L-glutamic acid through a dTDP-4-dehydro-6-deoxy-D-glucose transaminase resulting in the release of oxoglutaric acid and dTDP-thomosamine. The latter compound interacts with acetyl-coa through a dTDP-fucosamine acetyltransferase resulting in a Coenzyme A, a hydrogen Ion and a TDP-Fuc4NAc. Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate then interacts with a TDP--Fuc4NAc through a 4-acetamido-4,6-dideoxy-D-galactose transferase resulting in a hydrogen ion, a dTDP and a Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate. This compound is then transported through a protein wzxE into the periplasmic space so that it can be incorporated into the outer membrane.
References
Secondary Metabolites: Enterobacterial Common Antigen Biosynthesis References
Danese PN, Oliver GR, Barr K, Bowman GD, Rick PD, Silhavy TJ: Accumulation of the enterobacterial common antigen lipid II biosynthetic intermediate stimulates degP transcription in Escherichia coli. J Bacteriol. 1998 Nov;180(22):5875-84.
Pubmed: 9811644
Meier-Dieter U, Starman R, Barr K, Mayer H, Rick PD: Biosynthesis of enterobacterial common antigen in Escherichia coli. Biochemical characterization of Tn10 insertion mutants defective in enterobacterial common antigen synthesis. J Biol Chem. 1990 Aug 15;265(23):13490-7.
Pubmed: 2166030
Ohta M, Ina K, Kusuzaki K, Kido N, Arakawa Y, Kato N: Cloning and expression of the rfe-rff gene cluster of Escherichia coli. Mol Microbiol. 1991 Aug;5(8):1853-62. doi: 10.1111/j.1365-2958.1991.tb00809.x.
Pubmed: 1722555
Meier-Dieter U, Barr K, Starman R, Hatch L, Rick PD: Nucleotide sequence of the Escherichia coli rfe gene involved in the synthesis of enterobacterial common antigen. Molecular cloning of the rfe-rff gene cluster. J Biol Chem. 1992 Jan 15;267(2):746-53.
Pubmed: 1730666
Anderson MS, Eveland SS, Price NP: Conserved cytoplasmic motifs that distinguish sub-groups of the polyprenol phosphate:N-acetylhexosamine-1-phosphate transferase family. FEMS Microbiol Lett. 2000 Oct 15;191(2):169-75. doi: 10.1111/j.1574-6968.2000.tb09335.x.
Pubmed: 11024259
Daniels DL, Plunkett G 3rd, Burland V, Blattner FR: Analysis of the Escherichia coli genome: DNA sequence of the region from 84.5 to 86.5 minutes. Science. 1992 Aug 7;257(5071):771-8. doi: 10.1126/science.1379743.
Pubmed: 1379743
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
Rahman A, Barr K, Rick PD: Identification of the structural gene for the TDP-Fuc4NAc:lipid II Fuc4NAc transferase involved in synthesis of enterobacterial common antigen in Escherichia coli K-12. J Bacteriol. 2001 Nov;183(22):6509-16. doi: 10.1128/JB.183.22.6509-6516.2001.
Pubmed: 11673418
Barr K, Rick PD: Physical map location of the rffC and rffA genes of Escherichia coli. J Bacteriol. 1993 Sep;175(17):5738-9. doi: 10.1128/jb.175.17.5738-5739.1993.
Pubmed: 8366065
Riley M, Abe T, Arnaud MB, Berlyn MK, Blattner FR, Chaudhuri RR, Glasner JD, Horiuchi T, Keseler IM, Kosuge T, Mori H, Perna NT, Plunkett G 3rd, Rudd KE, Serres MH, Thomas GH, Thomson NR, Wishart D, Wanner BL: Escherichia coli K-12: a cooperatively developed annotation snapshot--2005. Nucleic Acids Res. 2006 Jan 5;34(1):1-9. doi: 10.1093/nar/gkj405. Print 2006.
Pubmed: 16397293
Stevenson G, Neal B, Liu D, Hobbs M, Packer NH, Batley M, Redmond JW, Lindquist L, Reeves P: Structure of the O antigen of Escherichia coli K-12 and the sequence of its rfb gene cluster. J Bacteriol. 1994 Jul;176(13):4144-56. doi: 10.1128/jb.176.13.4144-4156.1994.
Pubmed: 7517391
Itoh T, Aiba H, Baba T, Hayashi K, Inada T, Isono K, Kasai H, Kimura S, Kitakawa M, Kitagawa M, Makino K, Miki T, Mizobuchi K, Mori H, Mori T, Motomura K, Nakade S, Nakamura Y, Nashimoto H, Nishio Y, Oshima T, Saito N, Sampei G, Seki Y, Horiuchi T, et al.: A 460-kb DNA sequence of the Escherichia coli K-12 genome corresponding to the 40.1-50.0 min region on the linkage map. DNA Res. 1996 Dec 31;3(6):379-92. doi: 10.1093/dnares/3.6.379.
Pubmed: 9097040
Rick PD, Barr K, Sankaran K, Kajimura J, Rush JS, Waechter CJ: Evidence that the wzxE gene of Escherichia coli K-12 encodes a protein involved in the transbilayer movement of a trisaccharide-lipid intermediate in the assembly of enterobacterial common antigen. J Biol Chem. 2003 May 9;278(19):16534-42. doi: 10.1074/jbc.M301750200. Epub 2003 Mar 5.
Pubmed: 12621029
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 SMP0000975
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