Pyridoxal 5'-phosphate → L-5-Fluorotryptophan

HRID 1250430Notes

Reaction equation

HRID 1250430 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3]O.S([O-])([O-])=O.[Na+].[Na+].CC1C(O)=C(C=O)C(COP(O)(O)=O)=CN=1.[OH-].[K+].[F:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][CH:41]=1)[NH:38][CH:37]=[CH:36]2>CO>[F:32][C:33]1[CH:34]=[C:35]2[C:39]([NH:38][CH:37]=[C:36]2[CH2:3][C@@H:2]([C:5]([OH:7])=[O:6])[NH2:1])=[CH:40][CH:41]=1

Participants

7

Reactant 5

HCID 1051Pyridoxal 5'-phosphateHCID 5951L-SerineHCID 14797Potassium HydroxideHCID 24437Sodium SulfiteHCID 678615-Fluoroindole

Product 1

HCID 688357L-5-Fluorotryptophan

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the same manner as in Example 1, the cell suspension of Proteus vulgaris ATCC 13315 was prepared. Subsequently, 50 ml of a solution containing 120 mg/ml L-serine, 8 mg/ml sodium sulfite and 0.2 mg/ml pyridoxal 5′-phosphate were adjusted to pH 8.8, using potassium hydroxide solution, to adjust the final volume to 80 ml (substrate solution B). Subsequently, 1 ml of cell suspension was added to the 8 ml of substrate solution B, to which was added 1 ml of a solution containing 200 mg/ml 5-fluoroindole dissolved in methanol, and was incubated at 37° C. After the reaction had proceeded for the times indicated in Table 2, the reaction was stopped with boiling for 5 minutes. The amount of 5-fluoro-L-tryptophan produced in the reaction solution for 2, 6, 18 and 30 hours of reaction is shown in Table 2.

Workup

  1. additionIn the same manner as in Example 1, the cell suspension of Proteus vulgaris ATCC 13315
  2. customwas prepared
  3. customwas incubated at 37° C

Sources & evidence

ORD record
ord-6227af56086d4cdc8255bbf52137f942
Source dataset
uspto-grants-2002_01
Patent number
US06338957B2

Reaction notes

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