DL-Serine → L-Tryptophan

HRID 1156393Notes

Reaction equation

HRID 1156393 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH2:10][CH:11]([C:14]([OH:16])=[O:15])[CH2:12]O>CCC(COC(C(N(CC[NH+](C)C)C)=O)(C1C=CC=CC=1)C1C=CC=CC=1)CC.[Cl-].[O-]S([O-])=O.[Na+].[Na+].CC1N=CC(COP(O)(O)=O)=C(C=O)C=1O>[NH2:10][C@H:11]([C:14]([OH:16])=[O:15])[CH2:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

6

Reactant 2

HCID 617DL-SerineHCID 798Indole

Product 1

HCID 6305L-TryptophanYield 81.7%

Reagents, catalysts & solvents 3

HCID 1051Pyridoxal 5'-phosphateCatalystHCID 24437Sodium SulfiteCatalystHCID 19153X 100Solvent

Conditions

Temperature
30 °C

Procedure

In 50 g of Triton X-100 was dissolved 20 g of indole, and 36 g of DL-serine, 1 g of Na2SO3, 100 mg of pyridoxal phosphate and the above-mentioned two kinds of cells collected by centrifugal separation were added to the solution so that the entire volume was 1 l. The reaction liquid was shaken at a temperature of 30° C. and pH of 8.5 for 72 hours to effect reaction. After the reaction, 28.5 g of L-tryptophan was formed and accumulated in the reaction liquid (the yield was 41% based on serine).

Workup

  1. customthe above-mentioned two kinds of cells collected by centrifugal separation
  2. additionwere added to the solution so that the entire volume
  3. customThe reaction liquid
  4. customreaction
  5. customAfter the reaction

Sources & evidence

ORD record
ord-d56553f21b0c44bb8d3d579960d98a3f
Source dataset
uspto-grants-1982_06
Patent number
US04335209

Reaction notes

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