Pyridoxal 5'-phosphate → (R)-2-Amino-5,5,5-trifluoropentanoic acid

HRID 418400

Reaction equation

HRID 418400 reaction equation
[F:1][C:2]([F:11])([F:10])[CH2:3][CH2:4][C:5](=O)[C:6]([OH:8])=[O:7].CC1[N:18]=CC(COP(O)(O)=O)=C(C=O)C=1O>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[F:1][C:2]([F:11])([F:10])[CH2:3][CH2:4][C@@H:5]([NH2:18])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 1051Pyridoxal 5'-phosphateHCID 142786005,5,5-Trifluoro-2-oxopentanoic acid

Product 1

HCID 7177181(R)-2-Amino-5,5,5-trifluoropentanoic acid

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Procedure

A solution containing 5,5,5-trifluoro-2-oxopentanoic acid (100 mg, 0.588 mmoles), R,S-alanine (200 mg, 2.244 mmoles), and 0.02 mM pyridoxal phosphate, in 0.1 M potassium phosphate buffer, pH 7.5, was incubated with R-transaminase AT-103 from Biocatalytics (5 mg, 44 units) or cloned R-transaminase from Bacillus thuringiensis SC16569 (0.5 mL, 10 units, BMS transaminase) at 30° C. in a total volume of 5 mL in 15 mL tubes for 44 h. Reaction yields of (R)-5,5,5-trifluoro-2-aminopentanoic acid of 49% and 48% were obtained with AT-103 and BMS transaminases, respectively. Ee was 100% in both cases.

Workup

  1. customReaction

Sources & evidence

ORD record
ord-94851d4bf4ef452c8d0c04fd47082b07
Source dataset
uspto-grants-2012_01
Patent number
US08093276B2

Linked notes

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