MetaCyc Pathway: 1,4-dihydroxy-2-naphthoate biosynthesis I

Enzyme View:

Pathway diagram: 1,4-dihydroxy-2-naphthoate biosynthesis I

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.

Superclasses: Biosynthesis Cofactors, Prosthetic Groups, Electron Carriers Biosynthesis Quinol and Quinone Biosynthesis 1,4-Dihydroxy-2-Naphthoate Biosynthesis

Some taxa known to possess this pathway include ? : Bacillus subtilis , Enterococcus faecalis , Escherichia coli K-12 substr. MG1655 , Mycobacterium avium complex (MAC) , Mycobacterium fortuitum , Mycobacterium kansasii , Mycobacterium phlei , Mycobacterium tuberculosis

Expected Taxonomic Range: Bacteria

1,4-dihydroxy-2-naphthoate is a branch point metabolite leading to the biosynthesis of menaquinone (vitamin K2, in bacteria), phylloquinone (vitamin K1 in plants), and many plant pigments, including some two-ring naphthoquinones (such as lawsone and juglone) and the three-ring anthraquinones (such as alizarin and munjistin). These pigments are mostly found in Rubiaceae, where at least some of them are phytoalexins involved in plant defense. Many of these pigments were used as dyes since the early human history.

The benzenoid ring (or A ring) of 1,4-dihydroxy-2-naphthoate is derived from chorismate, derived via the shikimate pathway. The quinone ring (or B ring) is formed by addition of 2-oxoglutarate.

Note that the plant pathway and the bacterial pathway differ at the step of o-succinylbenzoate-CoA ligase. The bacterial enzyme, shown here, hydrolyzes ATP to AMP and pyrophosphate. Plant enzymes, such as O-succinylbenzoate-CoA ligase from Galium mollugo, hydrolyze ATP to ADP and phosphate.

Superpathways: superpathway of chorismate metabolism , superpathway of demethylmenaquinol-8 biosynthesis , superpathway of menaquinol-13 biosynthesis , superpathway of menaquinol-12 biosynthesis , superpathway of menaquinol-11 biosynthesis , superpathway of menaquinol-10 biosynthesis , superpathway of menaquinol-8 biosynthesis I , superpathway of demethylmenaquinol-9 biosynthesis , superpathway of demethylmenaquinol-6 biosynthesis I , superpathway of menaquinol-9 biosynthesis , superpathway of menaquinol-7 biosynthesis , superpathway of menaquinol-6 biosynthesis I

Variants: 1,4-dihydroxy-2-naphthoate biosynthesis II (plants)

Unification Links: EcoCyc:PWY-5837

Created 05-Mar-2008 by Caspi R , SRI International
Revised 18-Apr-2008 by Keseler I , SRI International


Heide81: Heide L, Leistner E (1981). "Enzymatic synthesis of the coenzyme A ester of o-succinylbenzoic acid, an intermediate in menaquinone (vitamin K2) biosynthesis." FEBS Lett 128(2);201-4. PMID: 7262311

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

Badger05: Badger J, Sauder JM, Adams JM, Antonysamy S, Bain K, Bergseid MG, Buchanan SG, Buchanan MD, Batiyenko Y, Christopher JA, Emtage S, Eroshkina A, Feil I, Furlong EB, Gajiwala KS, Gao X, He D, Hendle J, Huber A, Hoda K, Kearins P, Kissinger C, Laubert B, Lewis HA, Lin J, Loomis K, Lorimer D, Louie G, Maletic M, Marsh CD, Miller I, Molinari J, Muller-Dieckmann HJ, Newman JM, Noland BW, Pagarigan B, Park F, Peat TS, Post KW, Radojicic S, Ramos A, Romero R, Rutter ME, Sanderson WE, Schwinn KD, Tresser J, Winhoven J, Wright TA, Wu L, Xu J, Harris TJ (2005). "Structural analysis of a set of proteins resulting from a bacterial genomics project." Proteins 60(4);787-96. PMID: 16021622

Bhasin03: Bhasin M, Billinsky JL, Palmer DR (2003). "Steady-state kinetics and molecular evolution of Escherichia coli MenD [(1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase], an anomalous thiamin diphosphate-dependent decarboxylase-carboligase." Biochemistry 42(46);13496-504. PMID: 14621995

Bhattacharyya97: Bhattacharyya DK, Kwon O, Meganathan R (1997). "Vitamin K2 (menaquinone) biosynthesis in Escherichia coli: evidence for the presence of an essential histidine residue in o-succinylbenzoyl coenzyme A synthetase." J Bacteriol 1997;179(19);6061-5. PMID: 9324253

BRENDA14: BRENDA team (2014). "Imported from BRENDA version existing on Aug 2014."

Buss01: Buss K, Muller R, Dahm C, Gaitatzis N, Skrzypczak-Pietraszek E, Lohmann S, Gassen M, Leistner E (2001). "Clustering of isochorismate synthase genes menF and entC and channeling of isochorismate in Escherichia coli." Biochim Biophys Acta 1522(3);151-7. PMID: 11779629

Butland05: Butland G, Peregrin-Alvarez JM, Li J, Yang W, Yang X, Canadien V, Starostine A, Richards D, Beattie B, Krogan N, Davey M, Parkinson J, Greenblatt J, Emili A (2005). "Interaction network containing conserved and essential protein complexes in Escherichia coli." Nature 433(7025);531-7. PMID: 15690043

Chen11: Chen M, Jiang M, Sun Y, Guo ZF, Guo Z (2011). "Stabilization of the second oxyanion intermediate by 1,4-dihydroxy-2-naphthoyl-coenzyme A synthase of the menaquinone pathway: spectroscopic evidence of the involvement of a conserved aspartic acid." Biochemistry 50(26);5893-904. PMID: 21627110

Chen13: Chen M, Ma X, Chen X, Jiang M, Song H, Guo Z (2013). "Identification of a Hotdog Fold Thioesterase Involved in the Biosynthesis of Menaquinone in Escherichia coli." J Bacteriol 195(12);2768-75. PMID: 23564174

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

Dawson08: Dawson A, Fyfe PK, Hunter WN (2008). "Specificity and reactivity in menaquinone biosynthesis: the structure of Escherichia coli MenD (2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexadiene-1-carboxylate synthase)." J Mol Biol 384(5);1353-68. PMID: 18983854

DiazMejia09: Diaz-Mejia JJ, Babu M, Emili A (2009). "Computational and experimental approaches to chart the Escherichia coli cell-envelope-associated proteome and interactome." FEMS Microbiol Rev 33(1);66-97. PMID: 19054114

Dosselaere01: Dosselaere F, Vanderleyden J (2001). "A metabolic node in action: chorismate-utilizing enzymes in microorganisms." Crit Rev Microbiol 27(2);75-131. PMID: 11450855

Driscoll92: Driscoll JR, Taber HW (1992). "Sequence organization and regulation of the Bacillus subtilis menBE operon." J Bacteriol 174(15);5063-71. PMID: 1629163

Emmons85: Emmons GT, Campbell IM, Bentley R (1985). "Vitamin K (menaquinone) biosynthesis in bacteria: purification and probable structure of an intermediate prior to o-succinylbenzoate." Biochem Biophys Res Commun 131(2);956-60. PMID: 3902015

Fang11: Fang M, Macova A, Hanson KL, Kos J, Palmer DR (2011). "Using substrate analogues to probe the kinetic mechanism and active site of Escherichia coli MenD." Biochemistry 50(40);8712-21. PMID: 21928762

Gerlt05: Gerlt JA, Babbitt PC, Rayment I (2005). "Divergent evolution in the enolase superfamily: the interplay of mechanism and specificity." Arch Biochem Biophys 433(1);59-70. PMID: 15581566

GOA01: GOA, DDB, FB, MGI, ZFIN (2001). "Gene Ontology annotation through association of InterPro records with GO terms."

GOA01a: GOA, MGI (2001). "Gene Ontology annotation based on Enzyme Commission mapping." Genomics 74;121-128.

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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