Methanol → Tiglic acid
Reaction equation
[CH3:1]/[C:2](=[CH:5]\[CH3:6])/C#N.[CH3:7]/[C:8](=[CH:11]/[CH3:12])/C#N.C(NC(=[O:18])C)C.C(#N)C.[CH3:22][OH:23]>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[CH3:1]/[C:2](=[CH:5]\[CH3:6])/[C:22]([OH:18])=[O:23].[CH3:7]/[C:8](=[CH:11]/[CH3:12])/[C:22]([OH:18])=[O:23]Participants
Reactant 5
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Reaction of a 1:1 Mixture of (E)- and (Z)2-Methyl-2-Butenenitrile with E. coli SS1001 Cells A 5.0 mL suspension of 0.500 g (wet cell paste) E. coli SS1001 cells (ATCC PTA-1177) in 50 mM potassium phosphate buffer (pH 7.0) was added to a mixture containing 4.91 mL of 50 mM potassium phosphate buffer (pH 7.0), 38.4 mg of (E)-2-methyl-2-butenenitrile (47.4 mM final concentration of (E)-2-methyl-2-butenenitrile), and 37.7 mg of (Z)-2-methyl-2-butenenitrile (46.5 mM final concentration of (Z)-2-methyl-2-butenenitrile), and the resulting suspension stirred at 25° C. Samples (0.100 mL) were mixed with 0.900 mL of 60 mM N-ethylacetamide (HPLC external standard) in 1:1 acetonitrile:methanol, the resulting mixture was mixed, centrifuged, and the supernatant analyzed by HPLC for (E)- and (Z)-2-methyl-2-butenenitrile and (E)- and (Z)-2-methyl-2-butenoic acid. After 23 h, the conversions of (E)-2-methyl-2-butenenitrile and (Z)-2-methyl-2-butenenitrile were 100% and 0%, respectively, and the yields of (E)-2-methyl-2-butenoic acid and (Z)-2-methyl-2-butenoic acid were 100% and 0%, respectively.
Sources & evidence
- ORD record
- ord-9410b4251a3140bb909c695ec5863478
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07285410B2
Reaction notes
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