Reaction #358222

ord-495ba43b2388481faeacbd3b18f0cc59

Reaction equation

CN
methylamine
O=S(=O)(O)O
sulfuric acid
O=C([O-])C(=O)Cc1ccccc1.[Na+]
sodium phenylpyruvate
[Na+].[OH-]
sodium hydroxide
O=C([O-])C(=O)Cc1ccccc1.[Na+]
sodium phenylpyruvate
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADPH
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
glucose
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
glucose
→
CN[C@@H](Cc1ccccc1)C(=O)O
N-methylphenylalanine

Reactants

CN
methylamine
O=S(=O)(O)O
sulfuric acid
O=C([O-])C(=O)Cc1ccccc1.[Na+]
sodium phenylpyruvate
[Na+].[OH-]
sodium hydroxide
—
Tris-hydrochloride
O=C([O-])C(=O)Cc1ccccc1.[Na+]
sodium phenylpyruvate
NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NADPH
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
glucose
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
glucose

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractioncell-free extract
  2. 2
    workup.ADDITIONwere added
  3. 3
    Otherto react at 30° C
  4. 4
    workup.ADDITIONan additional 30 mg was added
  5. 5
    Otherduring the reaction of 24 hours
  6. 6
    OtherUpon completion of the reaction

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07452704B2uspto-grants-2008_11