Pyridoxal 5'-phosphate → beta-Phenylcysteine

HRID 1291982Notes

Reaction equation

HRID 1291982 reaction equation
[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3]O.[C:8]1([SH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC1N=CC(COP(O)(O)=O)=C(C=O)C=1O.[OH-].[Na+]>>[C:8]1([S:14][CH2:3][C@@H:2]([C:5]([OH:7])=[O:6])[NH2:1])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 1051Pyridoxal 5'-phosphateHCID 5951L-SerineHCID 7969ThiophenolHCID 14798Sodium Hydroxide

Product 1

HCID 119462beta-Phenylcysteine

Conditions

Temperature
35 °C

Procedure

A cell mass of Escherichia coli MT-10242 was obtained in a similar manner to Experiment 1. To 500 g of an aqueous solution containing 6% of L-serine, 6.2% of thiophenol and 25 ppm of pyridoxal phosphate and having a pH of 9.5 (adjusted with NaOH), the cells were added to a concentration of 0.8% as calculated based on dry cells. The resultant mixture was stirred at 35° C. for 20 hours under a nitrogen gas atmosphere. During this stirring, the stirring power was controlled at 16 W per liter of the reaction mixture. The molar yield of S-phenyl-L-cysteine so formed was 87% based on the charged L-serine.

Workup

  1. customwas obtained in a similar manner
  2. additionthe cells were added to a concentration of 0.8%
  3. customon dry cells

Sources & evidence

ORD record
ord-82ac135bd4a044f5a432c25c06c7051a
Source dataset
uspto-grants-1998_05
Patent number
US05756319

Reaction notes

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