Sulfuric Acid → N-Methylphenylalanine

HRID 271040

Reaction equation

HRID 271040 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.[Na+].[CH:14]1[N:15]=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3OP(O)(O)=O)C=2N=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.CN.S(=O)(=O)(O)O.[OH-].[Na+]>>[CH3:14][NH:15][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

7

Reactant 6

HCID 1118Sulfuric AcidHCID 5884NADPHHCID 6329MethylamineHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 23667645Sodium phenylpyruvate2×

Product 1

HCID 6951135N-Methylphenylalanine

Procedure

In a 50-mL beaker, 5.88 ml of 40 mM Tris-hydrochloride buffer (pH 8.0) containing 60 mg of sodium phenylpyruvate, 2.3 mg of NADPH, 35 U of glucose dehydrogenase, and 1 g of glucose was placed, to which 5.88 mL of 240 mM methylamine adjusted to pH 8.0 with sulfuric acid and 3.25 mL of the above cell-free extract were added, and the mixture was allowed to react at 30° C. The reaction was conducted while stirring and adjusting pH to 8.0 with 1 N aqueous sodium hydroxide solution. A portion of the reaction solution was analyzed by HPLC at regular intervals. When the substrate sodium phenylpyruvate was depleted, an additional 30 mg was added and the reaction was continued. This process was repeated 8 times during the reaction of 24 hours. Upon completion of the reaction, the amount of N-methylphenylalanine produced was 146 mg.

Workup

  1. extractioncell-free extract
  2. additionwere added
  3. customto react at 30° C
  4. additionan additional 30 mg was added
  5. customduring the reaction of 24 hours
  6. customUpon completion of the reaction

Sources & evidence

ORD record
ord-495ba43b2388481faeacbd3b18f0cc59
Source dataset
uspto-grants-2008_11
Patent number
US07452704B2

Linked notes

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