Phenylpyruvic acid → Atrolactic acid, (-)-

HRID 597761

Reaction equation

HRID 597761 reaction equation
[C:1]1([CH2:7][C:8](=O)C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13]([O-:15])=[O:14].[Na+].C1N=C(N)C2N=CN([C@@H]3[O:30][C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1>P([O-])([O-])([O-])=O>[C:1]1([C@@:7]([CH3:8])([OH:30])[C:13]([OH:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 997Phenylpyruvic acidHCID 439153NadhHCID 2723810Sodium Formate

Product 1

HCID 736858Atrolactic acid, (-)-

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

100 mg of the lyophilized, surface expressing E. coli was suspended with 100 mg of phenylpyruvic acid, 7 mg of sodium formate and 1.32 mg of NAD in 10 mL of 0.1 M phosphate buffer (pH 7.0) solution and stirred for 48 hours for reaction. After completion of the reaction, the solution was centrifuged at 12,000 rpm for 3 minutes to remove cells and obtain the supernatant. The obtained solution was adjusted to pH 2.0, extracted 5 times with 5 mL of ethyl acetate and subjected to liquid chromatography (column: Chiralcel OD-H; flow rate: 0.5 mL/min; solvent: Hexane/iso-propanol/tri-fluoroacetic acid=80:20:1 (volume); detection: UV 210 nm). As a result, (R)-phenyl lactic acid with an optical purity of 90% or better was obtained.

Workup

  1. customAfter completion of the reaction
  2. waitthe solution was centrifuged at 12,000 rpm for 3 minutes
  3. customto remove cells
  4. customobtain the supernatant
  5. extractionextracted 5 times with 5 mL of ethyl acetate

Sources & evidence

ORD record
ord-898fca7fd26448acb13e29738e91fadb
Source dataset
uspto-grants-2011_03
Patent number
US07897366B2

Linked notes

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