L-(+)-Cysteine → HCID 29719, compound

HRID 1941109Notes

Reaction equation

HRID 1941109 reaction equation
[CH:1]1[C:8]([CH2:9][C@H:10]([NH2:14])[C:11]([OH:13])=[O:12])=[CH:7][C:5](=[O:6])[C:3](=[O:4])[CH:2]=1.[NH2:15][C@H:16]([C:19]([OH:21])=[O:20])[CH2:17][SH:18]>>[CH:7]1[C:5]([OH:6])=[C:3]([OH:4])[C:2]([S:18][CH2:17][CH:16]([NH2:15])[C:19]([OH:21])=[O:20])=[CH:1][C:8]=1[CH2:9][CH:10]([NH2:14])[C:11]([OH:13])=[O:12]

Participants

3

Reactant 2

HCID 5862L-(+)-CysteineHCID 439316(alpha-S)-alpha-Amino-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acid2×

Product 1

HCID 29719HCID 29719, compound

Procedure

The other pathway from dopaquinone to melanin involves the addition of cysteine to dopaquinone to produce 5-S-cysteinyldopa, followed by the oxidation of 5-S-cysteinyldopa to 5-S-cysteinyldopaquinone. A ring closure of the 5-S-cysteinyldopaquinone then yields 7-alanyl-5-hydroxy-3-carboxy-2H-1,4-benzothiazine which is subsequently decarboxylated to yield 7-alanyl-5-hydroxy-2H-1,4-benzothiazine. At this point, the 7-alanyl-5-hydroxy-2H-1,4-benzothiazine is converted to melanin and pheomelanin. Tyrosinase does not play any additional role in this melanin production pathway.

Sources & evidence

ORD record
ord-acbdf1e896d54b948aeeb6049a45986c
Source dataset
uspto-grants-1997_12
Patent number
US05703051

Reaction notes

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