Indole-3-pyruvic acid → Monatin

Reaction equation

[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17](=[O:21])[C:18]([OH:20])=[O:19])=[CH:8]1>>[CH:12]1[CH:11]=[C:10]2[C:9]([CH2:16][C@@:17]([OH:21])([C:18]([OH:20])=[O:19])[CH2:3][C@H:2]([NH2:1])[C:4]([OH:6])=[O:5])=[CH:8][NH:7][C:15]2=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 803Indole-3-pyruvic acid

HCID 5950L-Alanine

Product 1

HCID 9860847Monatin

Procedure

The addition of alanine to indole-3-pyruvic acid produces monatin, and this reaction can be performed synthetically with a Grignard or organolithium reagent.

Sources & evidence

ORD record: ord-13818695195e4369b9e46ca0396cfdd4
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034610B2

Reaction notes

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