3-carbamoyl-alpha-picolinic acid production by imidase-catalyzed regioselective hydrolysis of 2,3-pyridinedicarboximide in a water-organic solvent, two-phase system.
3-Carbamoyl-alpha-picolinic acid, a versatile building block for the synthesis of agrochemicals and pharmaceuticals, was prepared by imidase-catalyzed regiospecific hydrolysis of 2,3-pyridinedicarboximide with intact Arthrobacter ureafaciens O-86 cells. Reactions were carried out in a water-organic solvent, two-phase system containing cyclohexanone at low pH to avoid spontaneous random hydrolysis. Under the optimized conditions, with the periodic addition of 2,3-pyridinedicarboximide (in total, 40 mM), the 3-carbamoyl-alpha-picolinic acid yield reached 36.6 mM in the water phase, with a molar conversion yield of 91.5% and a regioisomeric purity of 94.5%, in 2 h at pH 5.5.
Ogawa
J
J
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Japan.
Soong
C L
CL
Ito
M
M
Segawa
T
T
Prana
T
T
Prana
M S
MS
Shimizu
S
S
D000581:Amidohydrolases / Q000378:metabolism*; D001173:Arthrobacter / Q000378:metabolism*; D002219:Carbamates / Q000378:metabolism*; D002384:Catalysis; D003512:Cyclohexanones; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007094:Imides / Q000378:metabolism*; D010848:Picolinic Acids / Q000378:metabolism*; D011725:Pyridines / Q000378:metabolism*; D012997:Solvents; D013237:Stereoisomerism; D014867:Water
C418142:3-carbamoyl-picolinic acid; D002219:Carbamates; D003512:Cyclohexanones; D007094:Imides; D010848:Picolinic Acids; D011725:Pyridines; D012997:Solvents; D014867:Water; C036468:cyclohexanone; D000581:Amidohydrolases; C020047:dihydropyrimidinase; C418143:2,3-pyridinedicarboximide