Levodopa → (E)-6-amino-2-oxohex-3-enoic acid

HRID 1022361

Reaktionsgleichung

Reaktionsgleichung von HRID 1022361
[C:1]([C:9]([O-:11])=[O:10])(=[O:8])[C:2]1C=C[CH:5]=[CH:4][CH:3]=1.OC1C(C)=[N:15]C=C(C([O-])=O)C=1C([O-])=O.C([O-])(=O)C1C=C(O)C(O)=C(O)C=1.O=C([C@H](CC1C=C(O)C(O)=CC=1)N)O.C1(CC(=O)C([O-])=O)C=CC=CC=1.OC1C=C(C([O-])=O)C(=CC=1O)C([O-])=O.N1C=C(C([O-])=O)C(=O)NC1=O.C1C=C[C@](O)(C(O)=O)[C@@H](O)C=1>O>[NH2:15][CH2:5][CH2:4]/[CH:3]=[CH:2]/[C:1](=[O:8])[C:9]([OH:11])=[O:10]

Komponenten

10

Edukt 8

HCID 6047LevodopaHCID 440977(1R,6S)-1,6-dihydroxycyclohexa-2,4-dienecarboxylic acidHCID 1548898BenzoylformateHCID 45926973-PhenylpyruvateHCID 6971263Uracil-5-carboxylateHCID 1784328165-hydroxy-6-methylpyridine-3,4-dicarboxylateHCID 178524621HCID 178524621, VerbindungHCID 178524622HCID 178524622, Verbindung

Produkt 1

HCID 86674077(E)-6-amino-2-oxohex-3-enoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

There are no enzymes known in the art that catalyze the substrate L-2,3-dihydropicolinate to produce 5,6-dihydropyridine-2-carboxylate. However, there are a few decarboxylases that are able to decarboxylate ring mounted carboxylic acids. One skilled in the art would appreciate that it is likely that these enzymes may have, or could be engineered to have, activity towards L-2,3-dihydropicolinate. Examples of such decarboxylases include, but are not limited to, benzoylformate decarboxylase (EC 4.1.1.7), 3-hydroxy-2-methylpyridine-4,5-dicarboxylate decarboxylase (EC 4.1.1.51), pyrrole-2-carboxylase (EC 4.1.1.-), gallate decarboxylase (4.1.1.59), Dopa decarboxylase (EC 4.1.1.28), Phenylpyruvate decarboxylase (EC 4.1.1.43), 4,5-dihydroxyphthalate decarboxylase (EC 4.1.1.55), 5-dihydroxybenzoate decarboxylase (EC 4.1.1.62), Uracil-5-carboxylate decarboxylase (EC 4.1.1.66), and Cis-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylate dehydrogenase (EC 1.3.1.25). In a subsequent step, the 5,6-dihydropyridine-2-carboxylic acid ring is opened in the presence of water to produce (E)-6-amino-2-oxohex-3-enoic acid. This reaction is similar to the hydration of 2,3,4,5-terahydropyridine-2-carboxylic acid (in the lysine degradation pathway) and is likely to be spontaneous in the presence of water.

Quellen und Nachweise

ORD-Eintrag
ord-640a6be6df324c64b26c4546b83470a9
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722385B2

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