NADPH → Skatole

HRID 1270034Notes

Reaction equation

HRID 1270034 reaction equation
C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H:29]([N:31]5[CH:36]=[C:35]([C:37](N)=O)[CH2:34][CH:33]=[CH:32]5)[C@H:28](O)[C@@H:27]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3OP(O)(O)=O)C=2N=1.[Mg+2].[Cl-].[Cl-].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C(#N)C>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[NH:31]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:27][CH:28]=2)[C:35]([CH3:37])=[CH:36]1

Participants

6

Reactant 4

HCID 5884NADPH3×HCID 6049Ethylenediaminetetraacetic AcidHCID 6342AcetonitrileHCID 5360315Magnesium Chloride

Product 1

HCID 6736Skatole

Reagents, catalysts & solvents 1

HCID 24243Trisodium PhosphateSolvent

Procedure

Microsomal incubations. Two mg microsomal protein was incubated with 0.4 mM 3MI and 4 mM NADPH in 0.05M sodium phosphate buffer (pH 7.4) containing 5 mM MgCl2 and 1 mM EDTA for 30 min at 37.degree. C. (production of metabolites was determined to be linear over a range of 10 to 40 min). Incubation volumes were 0.5 ml. Reactions were started by the addition of NADPH after 3-minute preincubation periods at 37° C., and stopped with 0.5 ml of ice-cold acetonitrile. Incubations of all 30 samples were run in duplicate and for control incubations NADPH was omitted. After the addition of acetonitrile the mixture was vortexed and centrifuged at 5000 rpm for 20 min. A 50 μl aliquot of the clear supernatant was analyzed by high-performance liquid chromatography (HPLC).

Workup

  1. customover a range of 10 to 40 min

Sources & evidence

ORD record
ord-a70b73ab4ce84406882fac4b0fe6f5d0
Source dataset
uspto-grants-2007_04
Patent number
US07202035B2

Reaction notes

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