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

HRID 1950688

Reaction equation

HRID 1950688 reaction equation
[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]

Participants

10

Reactant 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, compoundHCID 178524622HCID 178524622, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Sources & evidence

ORD record
ord-2e8b260e8b06494eba5966f2756559ee
Source dataset
uspto-grants-2013_03
Patent number
US08404465B2

Linked notes

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