Reaction #1355845

ord-a46c6bbc39e142bfbbc8233d2afda969

Reaction equation

C/C=C(\C)C#N
(E)-2-methyl-2-butenenitrile
C/C=C(/C)C#N
(Z)-2-methyl-2-butenenitrile
C/C=C(\C)C#N
(E)-2-methyl-2-butenenitrile
C/C=C(\C)C#N
(E)-2-methyl-2-butenenitrile
C/C=C(/C)C#N
(Z)-2-methyl-2-butenenitrile
C/C=C(/C)C#N
(Z)-2-methyl-2-butenenitrile
CCNC(C)=O
N-ethylacetamide
CC#N
acetonitrile
CO
methanol
C/C=C(\C)C(=O)O
(E)-2-methyl-2-butenoic acid
C/C=C(/C)C(=O)O
(Z)-2-methyl-2-butenoic acid

Conditions

Temperature
35°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Procedure

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 4.80 mL of 50 mM potassium phosphate buffer (pH 7.0), 80.5 mg of (E)-2-methyl-2-butenenitrile (100 mM final concentration of (E)-2-methyl-2-butenenitrile), and 80.7 mg of (Z)-2-methyl-2-butenenitrile (100 mM final concentration of (Z)-2-methyl-2-butenenitrile), and the resulting suspension stirred at 35° 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 6 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 99% and 0%, respectively.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07198926B2uspto-grants-2007_04