L-Tryptophan → D-Alanine

HRID 1363916Notes

Reaction equation

N[C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH2:16][C@@H:17]([C:28]([OH:30])=[O:29])[CH2:18]C1C2C(=CC=CC=2)NC=1.C([O-])(=O)C(C)=O>>[NH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:3][C:2](=[O:29])[C:13]([O-:15])=[O:14])=[CH:5]1.[NH2:16][C@@H:17]([C:28]([OH:30])=[O:29])[CH3:18]

Participants

Reactant 3

HCID 6305L-Tryptophan2×

HCID 9060D-Tryptophan2×

HCID 107735Pyruvate

Product 2

HCID 71080D-Alanine

HCID 54603373-(1H-Indol-3-yl)-2-oxopropanoate

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.

Sources & evidence

ORD record: ord-b67ca4c44e1647458efeb30008d43f0c
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888081B2

Reaction notes

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