Pyridoxal 5'-phosphate → L-Phenylalanine

HRID 1906131Notes

Reaction equation

HRID 1906131 reaction equation
[C:1]1([CH2:7][C:8](=O)[C:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C@H](C([O-])=O)CC([O-])=O.[NH4+].[NH4+].CC1C(O)=C(C=O)C(COP(O)(O)=O)=CN=1>O>[NH2:13][C@H:8]([C:9]([OH:11])=[O:10])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1051Pyridoxal 5'-phosphateHCID 45926973-Phenylpyruvate2×HCID 86590683Ammonium Aspartate

Product 1

HCID 6140L-Phenylalanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A batch type process wherein the catalyst compositions are stirred in from 0.01 to 0.5 molar (preferably 0.05 to 0.3 molar) solution of phenylpyruvate in the presence of 0.015 to 0.75 molar ammonium L-aspartate (preferably 0.075 to 0.5 molar) and 0.4 to 0.000001 mmolar pyridoxal 5-phosphate (preferably 0.04 to 0.0004 mmolar in water at 5.0 to 10.0 pH (preferably 7.5 to 9.5 pH) for periods of 1.0 to 100 hours (preferably 8 to 48 hours) at temperatures below 50° C. (preferably 20° to 40° C.). Broadly from 0.05 to 50 g of immobilized cells, preferably from 1.0 to 15 g, are used per 0.1 mole of starting phenylpyruvate. After the conversion, the catalyst compositions may be removed by filtration or the equivalent for reuse in converting fresh batches of phenylpyruvate solutions. The product solutions are obtained in a form suitable for conventional processing to isolate the L-phenylalanine (ion exchange chromotography, precipitation, filtration, washing, recrystallization, drying).

Workup

  1. customAfter the conversion, the catalyst compositions may be removed by filtration
  2. customThe product solutions are obtained in a form suitable for conventional processing

Sources & evidence

ORD record
ord-795c3417af074574be9989baebcc5cbf
Source dataset
uspto-grants-1987_03
Patent number
US04650755

Reaction notes

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