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

Enzyme View:

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

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.

Synonyms: DHNA biosynthesis

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 ? : Arabidopsis thaliana col , Galium mollugo , Rubia tinctorum , Synechocystis sp. PCC 6803

Expected Taxonomic Range: Cyanobacteria , Viridiplantae

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.

In plant cell cultures protein synthesis and enzyme activities of isochorismate synthase, O-succinylbenzoate synthase, and O-succinylbenzoate-CoA ligase were found coincide with quinone production [vanTegelen99, Sieweke92].

Note that the plant pathway and the bacterial pathway differ at the step of O-succinylbenzoate-CoA ligase. The plant enzyme, shown here, hydrolyzes ATP to ADP and phosphate. The bacterial enzymes, such as o-succinylbenzoate-CoA ligase from Escherichia coli K-12, hydrolyze ATP to AMP and pyrophosphate.

Citations: [Simantiras91, Kolkmann87]

Superpathways: superpathway of phylloquinol biosynthesis

Variants: 1,4-dihydroxy-2-naphthoate biosynthesis I

Created 08-Feb-2008 by Zhang P , TAIR
Revised 21-May-2008 by Caspi R , SRI International


Kolkmann87: Kolkmann R, Leistner E (1987). "4-2'-(carboxyphenyl)-4-oxobutyryl coenzyme A ester, an intermediate in vitamin K (menaquinone) biosynthesis." Z. Naturforsch., 42c, 1207-1214.

Sieweke92: Sieweke, Hans-Jurgen, Leistner, Eckhard (1992). "O-succinylbenzoate: coenzyme A ligase from anthraquinone producing cell suspension cultures of Galium mollugo." Phytochemistry 31(7): 2329-2335.

Simantiras89: Simantiras M, Leistner E (1989). "Formation of o-succinylbenzoic acid from iso-chorismic acid in protein extracts from anthraquinone-producing plant cell suspension cultures." Phytochemistry, 28, 1381-1382.

Simantiras91: Simantiras M, Leistner E (1991). "Cell free synthesis of O-succinylbenzoic acid in protein extracts from anthraquinone and phylloquinone (vitamin K1) producing plant cell suspension cultures. Occurrence of intermediates between isochorismic and O-succinylbenzoic acid." Z. Naturforsch., 46c, 364-370.

vanTegelen99: van Tegelen, Leon JP, Bongaerts, Roger JM, Croes, AntonF, Verpoorte, Robert, Wullems, George J (1999). "Isochorismate synthase isoforms from elicited cell cultures of Rubia tinctorum." Phytochemistry 51:263-269.

Widhalm12: Widhalm JR, Ducluzeau AL, Buller NE, Elowsky CG, Olsen LJ, Basset GJ (2012). "Phylloquinone (Vitamin K(1) ) Biosynthesis in Plants: Two Peroxisomal Thioesterases of Lactobacillales Origin Hydrolyze 1,4-Dihydroxy-2-Naphthoyl-Coa." Plant J. PMID: 22372525

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

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

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

Chen11b: 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

Chen13a: 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

Dillon04: Dillon SC, Bateman A (2004). "The Hotdog fold: wrapping up a superfamily of thioesterases and dehydratases." BMC Bioinformatics 5;109. PMID: 15307895

Fang11a: 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

Gross06b: Gross J, Cho WK, Lezhneva L, Falk J, Krupinska K, Shinozaki K, Seki M, Herrmann RG, Meurer J (2006). "A plant locus essential for phylloquinone (vitamin K1) biosynthesis originated from a fusion of four eubacterial genes." J Biol Chem 281(25);17189-96. PMID: 16617180

Heide82: Heide L, Arendt S, Leistner E (1982). "Enzymatic synthesis, characterization, and metabolism of the coenzyme A ester of o-succinylbenzoic acid, an intermediate in menaquinone (vitamin K2) biosynthesis." J Biol Chem 1982;257(13);7396-400. PMID: 7045104

Heide82a: Heide L, Kolkmann R, Arendt S, Leistner E (1982). "Enzymic synthesis of o-succinylbenzoyl-CoA in cell-free extracts of anthraquinone producing Galium mollugo L. cell suspension cultures." Plant Cell Reports, 1, 180-182.

Huycke01: Huycke MM, Moore D, Joyce W, Wise P, Shepard L, Kotake Y, Gilmore MS (2001). "Extracellular superoxide production by Enterococcus faecalis requires demethylmenaquinone and is attenuated by functional terminal quinol oxidases." Mol Microbiol 42(3);729-40. PMID: 11722738

Jiang07: Jiang M, Cao Y, Guo ZF, Chen M, Chen X, Guo Z (2007). "Menaquinone biosynthesis in Escherichia coli: identification of 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate as a novel intermediate and re-evaluation of MenD activity." Biochemistry 46(38);10979-89. PMID: 17760421

Jiang08: Jiang M, Chen X, Guo ZF, Cao Y, Chen M, Guo Z (2008). "Identification and Characterization of (1R,6R)-2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate Synthase in the Menaquinone Biosynthesis of Escherichia coli." Biochemistry 47(11);3426-34. PMID: 18284213

Jiang09a: Jiang M, Chen X, Wu XH, Chen M, Wu YD, Guo Z (2009). "Catalytic mechanism of SHCHC synthase in the menaquinone biosynthesis of Escherichia coli: identification and mutational analysis of the active site residues." Biochemistry 48(29);6921-31. PMID: 19545176

Jiang10: Jiang M, Chen M, Guo ZF, Guo Z (2010). "A bicarbonate cofactor modulates 1,4-dihydroxy-2-naphthoyl-coenzyme a synthase in menaquinone biosynthesis of Escherichia coli." J Biol Chem 285(39);30159-69. PMID: 20643650

Johnson00a: Johnson TW, Shen G, Zybailov B, Kolling D, Reategui R, Beauparlant S, Vassiliev IR, Bryant DA, Jones AD, Golbeck JH, Chitnis PR (2000). "Recruitment of a foreign quinone into the A(1) site of photosystem I. I. Genetic and physiological characterization of phylloquinone biosynthetic pathway mutants in Synechocystis sp. pcc 6803." J Biol Chem 275(12);8523-30. PMID: 10722690

Kerbarh05: Kerbarh O, Ciulli A, Howard NI, Abell C (2005). "Salicylate biosynthesis: overexpression, purification, and characterization of Irp9, a bifunctional salicylate synthase from Yersinia enterocolitica." J Bacteriol 187(15);5061-6. PMID: 16030197

Kolappan07: Kolappan S, Zwahlen J, Zhou R, Truglio JJ, Tonge PJ, Kisker C (2007). "Lysine 190 is the catalytic base in MenF, the menaquinone-specific isochorismate synthase from Escherichia coli: implications for an enzyme family." Biochemistry 46(4);946-53. PMID: 17240978

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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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