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Pathway Description
Menaquinol Biosythesis
Escherichia coli
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2015-09-11
Last Updated: 2019-09-12
Menaquinol biosynthesis starts with chorismate being metabolized into isochorismate through a isochorismate synthase. Isochorismate then interacts with 2-oxoglutare and a hydrogen ion through a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase resulting in the release of a carbon dioxide and a 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate. The latter compound then interacts with (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase resulting in the release of a pyruvate and a (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate. This compound is the dehydrated through a o-succinylbenzoate synthase resulting in the release of a water molecule and a 2-succinylbenzoate. This compound then interacts with a coenzyme A and an ATP through a o-succinylbenzoate CoA ligase resulting in the release of a diphosphate, a AMP and a succinylbenzoyl-CoA. The latter compound interacts with a hydrogen ion through a 1,4-dihydroxy-2-naphthoyl-CoA synthase resulting in the release of a water molecule or a 1,4-dihydroxy-2-naphthoyl-CoA. This compound then interacts with water through a 1,4-dihydroxy-2-naphthoyl-CoA thioesterase resulting in the release of a coenzyme A, a hydrogen ion and a 1,4-dihydroxy-2-naphthoate.
The 1,4-dihydroxy-2-naphthoate can interact with either farnesylfarnesylgeranyl-PP or octaprenyl diphosphate and a hydrogen ion through a 1,4-dihydroxy-2-naphthoate octaprenyltransferase resulting in a release of a carbon dioxide, a pyrophosphate and a demethylmenaquinol-8. This compound then interacts with SAM through a bifunctional 2-octaprenyl-6-methoxy-1,4-benzoquinone methylase and S-adenosylmethionine:2-DMK methyltransferase resulting in a hydrogen ion, a s-adenosyl-L-homocysteine and a menaquinol.
References
Menaquinol Biosythesis References
Chen M, Ma X, Chen X, Jiang M, Song H, Guo Z: Identification of a hotdog fold thioesterase involved in the biosynthesis of menaquinone in Escherichia coli. J Bacteriol. 2013 Jun;195(12):2768-75. doi: 10.1128/JB.00141-13. Epub 2013 Apr 5.
Pubmed: 23564174
Bentley R, Meganathan R: Vitamin K biosynthesis in bacteria--precursors, intermediates, enzymes, and genes. J Nat Prod. 1983 Jan;46(1):44-59.
Pubmed: 6406647
Collins MD, Jones D: Distribution of isoprenoid quinone structural types in bacteria and their taxonomic implication. Microbiol Rev. 1981 Jun;45(2):316-54.
Pubmed: 7022156
Huang H, Levin EJ, Liu S, Bai Y, Lockless SW, Zhou M: Structure of a membrane-embedded prenyltransferase homologous to UBIAD1. PLoS Biol. 2014 Jul 22;12(7):e1001911. doi: 10.1371/journal.pbio.1001911. eCollection 2014 Jul.
Pubmed: 25051182
Meganathan R: Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms. Vitam Horm. 2001;61:173-218.
Pubmed: 11153266
Shineberg B, Young IG: Biosynthesis of bacterial menaquinones: the membrane-associated 1,4-dihydroxy-2-naphthoate octaprenyltransferase of Escherichia coli. Biochemistry. 1976 Jun 29;15(13):2754-8.
Pubmed: 949474
Young IG: Biosynthesis of bacterial menaquinones. Menaquinone mutants of Escherichia coli. Biochemistry. 1975 Jan 28;14(2):399-406.
Pubmed: 1091286
Bentley R, Meganathan R: Biosynthesis of vitamin K (menaquinone) in bacteria. Microbiol Rev. 1982 Sep;46(3):241-80.
Pubmed: 6127606
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
Popp JL: Sequence and overexpression of the menD gene from Escherichia coli. J Bacteriol. 1989 Aug;171(8):4349-54. doi: 10.1128/jb.171.8.4349-4354.1989.
Pubmed: 2666397
Daruwala R, Kwon O, Meganathan R, Hudspeth ME: A new isochorismate synthase specifically involved in menaquinone (vitamin K2) biosynthesis encoded by the menF gene. FEMS Microbiol Lett. 1996 Jul 1;140(2-3):159-63. doi: 10.1016/0378-1097(96)00173-5.
Pubmed: 8764478
Yamamoto Y, Aiba H, Baba T, Hayashi K, Inada T, Isono K, Itoh T, Kimura S, Kitagawa M, Makino K, Miki T, Mitsuhashi N, Mizobuchi K, Mori H, Nakade S, Nakamura Y, Nashimoto H, Oshima T, Oyama S, Saito N, Sampei G, Satoh Y, Sivasundaram S, Tagami H, Horiuchi T, et al.: Construction of a contiguous 874-kb sequence of the Escherichia coli -K12 genome corresponding to 50.0-68.8 min on the linkage map and analysis of its sequence features. DNA Res. 1997 Apr 28;4(2):91-113. doi: 10.1093/dnares/4.2.91.
Pubmed: 9205837
Jiang M, Chen X, Guo ZF, Cao Y, Chen M, Guo Z: Identification and characterization of (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase in the menaquinone biosynthesis of Escherichia coli. Biochemistry. 2008 Mar 18;47(11):3426-34. doi: 10.1021/bi7023755. Epub 2008 Feb 20.
Pubmed: 18284213
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
Sharma V, Meganathan R, Hudspeth ME: Menaquinone (vitamin K2) biosynthesis: cloning, nucleotide sequence, and expression of the menC gene from Escherichia coli. J Bacteriol. 1993 Aug;175(15):4917-21. doi: 10.1128/jb.175.15.4917-4921.1993.
Pubmed: 8335646
Palmer DR, Garrett JB, Sharma V, Meganathan R, Babbitt PC, Gerlt JA: Unexpected divergence of enzyme function and sequence: "N-acylamino acid racemase" is o-succinylbenzoate synthase. Biochemistry. 1999 Apr 6;38(14):4252-8. doi: 10.1021/bi990140p.
Pubmed: 10194342
Sharma V, Hudspeth ME, Meganathan R: Menaquinone (vitamin K2) biosynthesis: localization and characterization of the menE gene from Escherichia coli. Gene. 1996 Feb 2;168(1):43-8. doi: 10.1016/0378-1119(95)00721-0.
Pubmed: 8626063
Sharma V, Suvarna K, Meganathan R, Hudspeth ME: Menaquinone (vitamin K2) biosynthesis: nucleotide sequence and expression of the menB gene from Escherichia coli. J Bacteriol. 1992 Aug;174(15):5057-62. doi: 10.1128/jb.174.15.5057-5062.1992.
Pubmed: 1629162
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
Suvarna K, Stevenson D, Meganathan R, Hudspeth ME: Menaquinone (vitamin K2) biosynthesis: localization and characterization of the menA gene from Escherichia coli. J Bacteriol. 1998 May;180(10):2782-7.
Pubmed: 9573170
Plunkett G 3rd, Burland V, Daniels DL, Blattner FR: Analysis of the Escherichia coli genome. III. DNA sequence of the region from 87.2 to 89.2 minutes. Nucleic Acids Res. 1993 Jul 25;21(15):3391-8. doi: 10.1093/nar/21.15.3391.
Pubmed: 8346018
Lee PT, Hsu AY, Ha HT, Clarke CF: A C-methyltransferase involved in both ubiquinone and menaquinone biosynthesis: isolation and identification of the Escherichia coli ubiE gene. J Bacteriol. 1997 Mar;179(5):1748-54. doi: 10.1128/jb.179.5.1748-1754.1997.
Pubmed: 9045837
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
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