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DHI and DHICA polymerize forming eumelanin
Stable Identifier
R-HSA-5663050
Type
Reaction [omitted]
Species
Homo sapiens
Compartment
melanosome lumen
,
melanosome membrane
ReviewStatus
5/5
Locations in the PathwayBrowser
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Metabolism (Homo sapiens)
Metabolism of amino acids and derivatives (Homo sapiens)
Melanin biosynthesis (Homo sapiens)
DHI and DHICA polymerize forming eumelanin (Homo sapiens)
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The layout of this reaction may differ from that in the pathway view due to the constraints in pathway layout
Eumelanin is a stacked, aggregated oligomer, or heterogeneous polymer consisting of units representing different oxidative states of 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA), plus pyrrole units derived from their peroxidative cleavage (Meredith & Sarna 2006, Ito & Wakamatsu 2008). Eumelanin was thought to consist mostly of DHI but this was reconsidered when chemical degradation revealed that natural eumelanins include DHI and DHICA units in a nearly equal ratio (Ito 1986, d'Ischia et al. 2013). DHICA is produced by tautomerization of dopachrome.The oxidative polymerization of DHI can be catalyzed by Tyrosinase (TYR) (Tripathi et al. 1992) but may also be effectively catalysed by redox exchange with dopaquinone (Edge et al. 2006). Redox is likely to be less efficient for DHICA. In mice, the tyrosinase-related protein Tyrp1 can oxidize DHICA (Kobayashi et al. 1994) but human TYRP1 is unable to catalyze the same reaction (Boissy et al. 1998). Instead, human TYR oxidizes DHICA, DHI, tyrosine and dopa.
Literature References
PubMed ID
Title
Journal
Year
17083485
The physical and chemical properties of eumelanin
Sarna, T
,
Meredith, P
Pigment Cell Res.
2006
Participants
Input
DHI, DHICA [melanosome lumen]
L-Dopaquinone [melanosome lumen]
Output
Eumelanin [melanosome lumen]
(Homo sapiens)
L-Dopa [melanosome lumen]
Participates
as an event of
Melanin biosynthesis (Homo sapiens)
Catalyst Activity
monooxygenase activity of TYR:2xCu2+ [melanosome membrane]
Physical Entity
TYR:2xCu2+ [melanosome membrane]
(Homo sapiens)
Activity
monooxygenase activity (GO:0004497)
Orthologous Events
DHI and DHICA polymerize forming eumelanin (Bos taurus)
DHI and DHICA polymerize forming eumelanin (Caenorhabditis elegans)
DHI and DHICA polymerize forming eumelanin (Canis familiaris)
DHI and DHICA polymerize forming eumelanin (Dictyostelium discoideum)
DHI and DHICA polymerize forming eumelanin (Gallus gallus)
DHI and DHICA polymerize forming eumelanin (Mus musculus)
DHI and DHICA polymerize forming eumelanin (Rattus norvegicus)
DHI and DHICA polymerize forming eumelanin (Sus scrofa)
DHI and DHICA polymerize forming eumelanin (Xenopus tropicalis)
Authored
Jupe, S (2015-01-13)
Reviewed
d'Ischia, M (2015-02-13)
Ito, S (2015-02-13)
Created
Jupe, S (2015-01-15)
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