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Stizolobinate synthase

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Stizolobinate synthase (EC 1.13.11.30) is an enzyme that catalyzes the chemical reaction

 
O2
 
Rightward reaction arrow with minor substrate(s) from top left
 
 
 
2D representation of the chemical structure of Q27102516.
5-(L-alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde

The two substrates of this enzyme are L-DOPA and oxygen. Its initial product is 5-(L-alanin-3-yl)-2-hydroxy-cis,cis-muconate 6-semialdehyde.[1]

The intermediate readily cyclises and further oxidises, forming a 2-pyrone ring; this is stizolobinic acid, which is the product that is isolated and after which this enzyme is named.[2][3]

2D representation of the chemical structure of Q27102516.
intermediate
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q27236548.
stizolobinic acid
 

The oxidation step uses oxidised nicotinamide adenine dinucleotide as a cofactor and the enzyme also requires zinc. It belongs to the family of oxidoreductases, specifically those acting on single donors with O2 as oxidant and incorporation of two atoms of oxygen into the substrate (oxygenases). The oxygen incorporated need not be derived from O2. The systematic name of this enzyme class is 3,4-dihydroxy-L-phenylalanine:oxygen 4,5-oxidoreductase (recyclizing). It participates in tyrosine metabolism.[1]

Stizolobic acid

A separate enzyme, stizolobate synthase also present in higher plants cleaves L-DOPA in a way which produces the isomeric compound, stizolobic acid.[3]

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