Benzaldehyde → 2-Amino-4-hydroxy-4-phenylbutanoic acid

HRID 440164Notes

Reaction equation

[CH:1]1[CH:2]=[CH:3][C:4](N)=[C:5]([C:7]([CH2:9][C@H:10]([NH2:14])[C:11]([OH:13])=[O:12])=[O:8])[CH:6]=1.C(=O)C1C=CC=CC=1>>[NH2:14][CH:10]([CH2:9][CH:7]([OH:8])[C:5]1[CH:6]=[CH:1][CH:2]=[CH:3][CH:4]=1)[C:11]([OH:13])=[O:12]

Participants

Reactant 2

HCID 240Benzaldehyde

HCID 161166Kynurenine

Product 1

HCID 119975642-Amino-4-hydroxy-4-phenylbutanoic acid

Procedure

The aldol reaction of L-kynurenine and benzaldehyde catalyzed by kynureninase was found to proceed to give predominantly (80%) the (αS, γR) diastereomer of α-amino-γ-hydroxybenzenebutanoic acid.

Sources & evidence

ORD record: ord-4b585bc51312416b92fcef5a1f124172
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05516936

Reaction notes

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