Levodopa → 5,6-Dihydroxyindole

HRID 1198091

Reaktionsgleichung

Reaktionsgleichung von HRID 1198091
N[C@H](C(O)=O)CC1C=CC(O)=CC=1.O=C([C@H:17]([CH2:19][C:20]1[CH:27]=[C:25]([OH:26])[C:23]([OH:24])=[CH:22][CH:21]=1)[NH2:18])O.C1C2C(=CC(C(C=2)=O)=O)NC1C(O)=O.C1C(O)=C2NC(C(O)=O)=C(C3SC4=CC(CC(N)C(O)=O)=CC(=O)C4=NC=3)SC2=CC=1CC(N)C(O)=O.CC1C(=O)C(=O)C2C3C4C(=C(C)C(C(C=4C4=CNC=1C=24)=O)=O)NC=3>>[OH:26][C:25]1[CH:27]=[C:20]2[C:21](=[CH:22][C:23]=1[OH:24])[NH:18][CH:17]=[CH:19]2

Komponenten

6

Edukt 5

HCID 6047LevodopaHCID 6057L-TyrosineHCID 119399Dopachrome2×HCID 6325610MelaninsHCID 102582077Eumelanins

Produkt 1

HCID 1146835,6-Dihydroxyindole

Versuchsvorschrift

As reported, for example, in Prota, Progress in the Chemist of Melanins and Related Metabolites, Med. Res. Reviews, 8:525-56 (1988), melanins are naturally occurring pigments present in hair and skin. In humans biosynthesis takes place in tyrosinase containing melanocytes. The tyrosinase enzyme catalyzes the hydroxylation of tyrosine to dopa and its subsequent oxidation to dopachrome. Once formed, dopachrome undergoes a series of complex reactions in the formation of eumelanins and phaeomelanins. Melanins provide black and deep brown pigments, and are formed by oxidative polymerization of 5,6-dihydroxyindole derived biogenetically during the melanogenesis. On the other hand, phaeomelanins provide yellow to reddish brown pigmentation to hair, and are formed by oxidative polymerization of cystein-S-yl-dopas via 1,4-benzothiazine intermediates.

Aufarbeitung

  1. additioncontaining melanocytes
  2. customOnce formed
  3. customMelanins provide black

Quellen und Nachweise

ORD-Eintrag
ord-14d7f07eea874e76bc9788326f81e766
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05279618

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