L-Phenylalanine → L-Tyrosine

HRID 1609702Notes

Reaction equation

HRID 1609702 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)C(N)(CO)C[OH:16].Cl.N1C2C(=NC=CN=2)C(=O)NC=1N>CC1(C)NC2C(N=C(N)NC=2NC1)=O>[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:16])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6140L-Phenylalanine3×HCID 93573Tromethamine hydrochlorideHCID 135398660Pterin

Product 1

HCID 6057L-Tyrosine

Reagents, catalysts & solvents 1

HCID 1784283612-amino-6,6-dimethyl-1,5,7,8-tetrahydropteridin-4-oneSolvent2×

Procedure

Absorbance Spectrum of Quinoid-6,6-Me2PH2Generated by Phenylalanine Hydroxylase. Spectra were taken of the q-6,6-Me2PH2 synthesized enzymatically from 6,6-Me2PH4, and a comparison made with the chemically produced compound. The spectrophotometer was baseline corrected with sample and reference cuvettes containing all of the reaction components (0.1M Tris·HCl, pH 7.4, 4 mM phenylalanine, 2500 units catalase, 0.3 unit phenylalanine hydroxylase) except pterin in a total volume of 0.99 ml. 6,6-Me2PH4 (10 μl of 10 mM) was then added to the sample and distilled H2O (10 μl) to the reference cuvette. Scanning was begun immediately and spectra taken at 2 minute intervals. The formation of q-6,6-Me2PH2 was complete within 4 minutes. After correction for tyrosine formed and phenylalanine consumed, the spectrum was within 3% of that produced by Br2 oxidation of 6,6-Me2PH4 (FIGURE).

Workup

  1. additioncontaining all
  2. distillationdistilled H2O (10 μl) to the reference cuvette
  3. waitThe formation of q-6,6-Me2PH2 was complete within 4 minutes

Sources & evidence

ORD record
ord-a42c435ce5e9469ebaddcb6a3e0cf4b7
Source dataset
uspto-grants-1995_03
Patent number
US05401844

Reaction notes

Loading…