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Pathway Description
Melanin Biosynthesis
Danio rerio
Metabolic Pathway
Melanin is used in the skin of zebrafish for camouflage, mimicry, communication and protection from the sun. It is also a pigment in the eyes. Melanin is produced by melanocytes, organelles within the skin cells. Eumelanins are brown and black pigments, while other melanins exist, pheomelanin being yellow and red pigments, and neuromelanin being used in the brain. All of these pigments require tyrosine to start their synthesis.
To start this pathway, tyrosine is transported into the melanosome by an amino acid transporter, and at this point it is metabolized to L-dopachrome . Within the melanosome membrane, L-dopachrome tautomerase converts L-dopachrome to 5,6-dihydroxyindole-2-carboxylic acid. This then interacts with tyrosinase-related protein 1a, which adds an oxygen molecule to form 5,6-indolequinone-2-carboxylic acid. This then undergoes a final reaction to form eumelanin.
Alternatively, L-dopachrome can spontaneously lose a carbon dioxide molecule, forming 5,6-dihydroxyindole. Following this, it can interact with tyrosinase to form indole-5,6-quinone. Finally, another reaction occurs, forming eumelanin from this compound.
References
Melanin Biosynthesis References
Ito S, Wakamatsu K: Chemistry of mixed melanogenesis--pivotal roles of dopaquinone. Photochem Photobiol. 2008 May-Jun;84(3):582-92. doi: 10.1111/j.1751-1097.2007.00238.x.
Pubmed: 18435614
Olivares C, Jimenez-Cervantes C, Lozano JA, Solano F, Garcia-Borron JC: The 5,6-dihydroxyindole-2-carboxylic acid (DHICA) oxidase activity of human tyrosinase. Biochem J. 2001 Feb 15;354(Pt 1):131-9. doi: 10.1042/0264-6021:3540131.
Pubmed: 11171088
Sparnins VL, Dagley S: Alternative routes of aromatic catabolism in Pseudomonas acidovorans and Pseudomonas putida: gallic acid as a substrate and inhibitor of dioxygenases. J Bacteriol. 1975 Dec;124(3):1374-81.
Pubmed: 1194238
Prieto MA, Diaz E, Garcia JL: Molecular characterization of the 4-hydroxyphenylacetate catabolic pathway of Escherichia coli W: engineering a mobile aromatic degradative cluster. J Bacteriol. 1996 Jan;178(1):111-20. doi: 10.1128/jb.178.1.111-120.1996.
Pubmed: 8550403
Potterf SB, Muller J, Bernardini I, Tietze F, Kobayashi T, Hearing VJ, Gahl WA: Characterization of a melanosomal transport system in murine melanocytes mediating entry of the melanogenic substrate tyrosine. J Biol Chem. 1996 Feb 23;271(8):4002-8. doi: 10.1074/jbc.271.8.4002.
Pubmed: 8626732
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