3-Carbamoyl-alpha-picolinic acid production by imidase-catalyzed regioselective hydrolysis of 2,3-pylidinedicarboximide in a water-organic solvent, two-phase system
J. Ogawa et al., 3-Carbamoyl-alpha-picolinic acid production by imidase-catalyzed regioselective hydrolysis of 2,3-pylidinedicarboximide in a water-organic solvent, two-phase system, APPL MICR B, 54(3), 2000, pp. 331-334
3-Carbamoyl-alpha-picolinic acid, a versatile building block for the synthe
sis of agrochemicals and pharmaceuticals, was prepared by imidase-catalyzed
regiospecific hydrolysis of 2,3-pyridinedicarboximide with intact Arthroba
cter ureafaciens O-86 cells. Reactions were carried out in a water-organic
solvent, two-phase system containing cyclohexanone at low pH to avoid spont
aneous random hydrolysis. Under the optimized conditions, with the periodic
addition of 2,3-pyridinedicarboximide (in total, 40 mM), the 3-carbamoyl-a
lpha-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.