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MetaCyc Pathway: indigo biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: indigo biosynthesis

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: BiosynthesisSecondary Metabolites Biosynthesis

Some taxa known to possess this pathway include : Baphicacanthus cusia, Persicaria tinctoria, Pseudomonas sp. NCIB9816-4

Expected Taxonomic Range: Bacteria , Viridiplantae

indican is the β-D-glucoside of indoxyl, and is found in several plant families, the most important being Acanthaceae, Asclepiadaceae, Apocynaceae, Fabaceae, and Polygonaceae. The function of indican in plants is still unknown.

After enzymic or chemical hydrolysis, indican can converted back to indoxyl, which can spontaneously dimerize (in the presence of oxygen) to indigo. Indigo was one of the most important dye compounds in the past, and is still an esteemed dye today.

The pathway for indican biosynthesis diverts from that of L-tryptophan at indole, which is produced from (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate by the tryptophan synthase subunit α. Indole is converted by dioxygenase systems (enzyme complexes that form cis-dihydrodiols) to cis-indole-2,3-dihydrodiol, which spontaneously eliminate a water molecule to form indoxyl. While dioxygenase enzymes from the plants that are konwn to produce indigo have not been studied yet, bacterial enzymes, such as naphthalene 1,2-dioxygenase complex from Pseudomonas putida, have been used successfully for the production of indican in strain of Escherichia coli engineered to produce indigo [Ensley83].

In the plant, indoxyl is converted to indican by indoxyl-UDPG glucosyltransferase. This enzyme has been purified from Baphicacanthus cusia [Marcinek00] and Persicaria tinctoria [Minami00]. However, as mentioned above, in the absence of this enzyme indoxyl can dimerize spontaneously to indigo.

Created 13-Oct-2008 by Caspi R, SRI International


Ensley83: Ensley BD, Ratzkin BJ, Osslund TD, Simon MJ, Wackett LP, Gibson DT (1983). "Expression of naphthalene oxidation genes in Escherichia coli results in the biosynthesis of indigo." Science 222(4620);167-9. PMID: 6353574

Marcinek00: Marcinek H, Weyler W, Deus-Neumann B, Zenk MH (2000). "Indoxyl-UDPG-glucosyltransferase from Baphicacanthus cusia." Phytochemistry 53(2);201-7. PMID: 10680172

Minami00: Minami Y, Nishimura O, Hara-Nishimura I, Nishimura M, Matsubara H (2000). "Tissue and intracellular localization of indican and the purification and characterization of indican synthase from indigo plants." Plant Cell Physiol 41(2);218-25. PMID: 10795317

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

Ensley82: Ensley BD, Gibson DT, Laborde AL (1982). "Oxidation of naphthalene by a multicomponent enzyme system from Pseudomonas sp. strain NCIB 9816." J Bacteriol 149(3);948-54. PMID: 7037744

Ensley83a: Ensley BD, Gibson DT (1983). "Naphthalene dioxygenase: purification and properties of a terminal oxygenase component." J Bacteriol 155(2);505-11. PMID: 6874638

Haigler90: Haigler BE, Gibson DT (1990). "Purification and properties of ferredoxinNAP, a component of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816." J Bacteriol 172(1);465-8. PMID: 2294093

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Resnick96: Resnick SM, Gibson DT (1996). "Regio- and stereospecific oxidation of fluorene, dibenzofuran, and dibenzothiophene by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4." Appl Environ Microbiol 62(11);4073-80. PMID: 8899998

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Tue May 3, 2016, biocyc14.