D-Alanine → Pyruvate

HRID 1363917Notes

Reaction equation

HRID 1363917 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11](=[O:15])[C:12]([O-:14])=[O:13])=[CH:2]1.[C:16]([O-:21])(=[O:20])[C:17]([CH3:19])=[O:18].C[C@H]1NCCNC1.[NH2:29][C@@H:30]([C:32]([OH:34])=[O:33])[CH3:31]>>[CH:6]1[CH:5]=[C:4]2[C:3]([CH2:10][C@@:11]([OH:15])([C:12]([OH:14])=[O:13])[CH2:31][C@H:30]([NH2:29])[C:32]([OH:34])=[O:33])=[CH:2][NH:1][C:9]2=[CH:8][CH:7]=1.[C:16]([O-:21])(=[O:20])[C:17]([CH3:19])=[O:18]

Participants

6

Reactant 4

HCID 71080D-AlanineHCID 107735PyruvateHCID 54603373-(1H-Indol-3-yl)-2-oxopropanoateHCID 73304342-Methylpiperazine, (R)-

Product 2

HCID 107735PyruvateHCID 9860847Monatin

Procedure

In a specific embodiment, L-tryptophan is converted to D-tryptophan using a tryptophan racemase. D-tryptophan then reacts with pyruvate via a broad specificity D-aminotransferase to produce indole-3-pyruvate and D-alanine. Indole-3-pyruvate then reacts with an R-specific aldolase and pyruvate to form R-α-keto acid monatin (R-MP). R-MP then reacts with a broad specificity D-aminotransferase and D-alanine to produce R,R monatin and pyruvate.

Workup

  1. customto form R-α-keto acid monatin (R-MP)

Sources & evidence

ORD record
ord-d27c9508ea0f45159b7e04dbaf5d9ed4
Source dataset
uspto-grants-2011_02
Patent number
US07888081B2

Reaction notes

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