Potassium Hydroxide → Morphine

HRID 1458505Notes

Reaction equation

HRID 1458505 reaction equation
Cl.[CH:2]1[C:18]2[CH2:17][C@H:16]3[N:19]([CH2:21][CH2:22][C@@:8]45[C@H:15]3[CH:14]=[CH:13][C@H:11]([OH:12])[C@@H:9]4[O:10][C:6]([C:7]=25)=[C:4]([OH:5])[CH:3]=1)[CH3:20].[OH-].[K+].C1C(CN2C(=O)C=CC2=O)CCC(C(ON2C(=O)CCC2=O)=O)C1>CN(C)C=O>[CH:2]1[C:18]2[CH2:17][C@H:16]3[N:19]([CH2:21][CH2:22][C@@:8]45[C@H:15]3[CH:14]=[CH:13][C@H:11]([OH:12])[C@@H:9]4[O:10][C:6]([C:7]=25)=[C:4]([OH:5])[CH:3]=1)[CH3:20]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 125175Succinimidyl 4-(N-maleimidomethyl)cyclohexanecarboxylateHCID 5464110Morphine Hydrochloride

Product 1

HCID 5288826Morphine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Morphine-HCTL (0.068 g, 1.3×10-4 mol, example 9) was dissolved in 5.7 ml of 70% dimethylformamide/30% water and 1.43 ml 1N potassium hydroxide was added. After 5 min the thiol concentration was determined by reaction with DTNB to be 16.9 mM. The morphine thiol -- (6.4 ml, 1.1×10-4 mol) was added with stirring to 26.7 ml SMCC-BSA, 15/1, (0.16 g, 2.4×10-6 mol). The container was purged with argon and the solution was stirred at room temperature for 2 hr. The protein solution was then dialyzed using a PYROSART module against 10 mM (2-(N-morpholino) ethane sulfonic acid, pH 5.77, and 29.5 ml of 5.39 mg/ml BSA-morphine was collected. The protein solution was frozen at -70° C.

Workup

  1. concentrationAfter 5 min the thiol concentration
  2. customwas determined by reaction with DTNB
  3. customThe container was purged with argon
  4. customThe protein solution was then dialyzed
  5. customwas collected
  6. temperatureThe protein solution was frozen at -70° C.

Sources & evidence

ORD record
ord-a35981d8995646fbb08b45f0161ebb34
Source dataset
uspto-grants-1998_12
Patent number
US05851776

Reaction notes

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