Acetonitrile → Aurone

HRID 734988Notes

Reaction equation

HRID 734988 reaction equation
CC[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([OH:23])[C:9]2[C@@H:15]3[CH:16]=[C:17](C)[CH2:18][CH2:19][C@H:14]3C(C)(C)O[C:10]=2[CH:11]=1.C([O-])(=[O:26])C.[Na+].C(#N)C.C(O)(C(F)(F)F)=O>C(O)C.O>[CH:18]1[CH:19]=[CH:14][C:15](/[CH:9]=[C:8]2/[C:7]([C:6]3[C:5]([O:23]/2)=[CH:4][CH:3]=[CH:10][CH:11]=3)=[O:26])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 16078TetrahydrocannabinolHCID 517045Sodium Acetate

Product 1

HCID 6537099Aurone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The reaction was started by adding 5 μl of THC, having an absorbance of 462 at 366 nm in ethanol, to 50 μl of 1 M sodium acetate buffer (pH 5.0) and 350 μl of crude enzyme solution diluted with water. After allowing to react for 1 hour at 30° C., and adding 100 μl of an aqueous solution of 90% (v/v) acetonitrile containing 1% (v/v) TFA to stop the reaction, activity was measured by HPLC. The crude enzyme solution in each purification step described later in Example 4 was measured.

Workup

  1. customto react for 1 hour at 30° C.
  2. customthe reaction, activity
  3. customThe crude enzyme solution in each purification step

Sources & evidence

ORD record
ord-2170f80914ec4a548ada80424fac8e11
Source dataset
uspto-grants-2009_09
Patent number
US07592436B2

Reaction notes

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