5-Cyanovaleramide production using immobilized Pseudomonas chlororaphis B23.
A biocatalytic process for the hydration of adiponitrile to 5-cyanovaleramide has been developed which can be run to higher conversion, produces more product per weight of catalyst, and generates significantly less waste products than alternate chemical processes. The biocatalyst consists of Pseudomonas chlororaphis B23 microbial cells immobilized in calcium alginate beads. The cells contain a nitrile hydratase (EC 4.2.1.84) which catalyzes the hydration of adiponitrile to 5-cyanovaleramide with high regioselectivity, and with less than 5% selectivity to byproduct adipamide. Fifty-eight consecutive batch reactions with biocatalyst recycle were run to convert a total of 12.7 metric tons of adiponitrile to 5-cyanovaleramide. At 97% adiponitrile conversion, the yield of 5-cyanovaleramide was 13.6 metric tons (93% yield, 96% selectivity), and the total weight of 5-cyanovaleramide produced per weight of catalyst was 3150 kg/kg (dry cell weight).
Hann
E C
EC
DuPont Life Sciences, Experimental Station, Wilmington, DE 19880-0328, USA.
Eisenberg
A
A
Fager
S K
SK
Perkins
N E
NE
Gallagher
F G
FG
Cooper
S M
SM
Gavagan
J E
JE
Stieglitz
B
B
Hennessey
S M
SM
DiCosimo
R
R
D000577:Amides / Q000737:chemistry* / Q000378:metabolism; D001709:Biotechnology / Q000379:methods*; D004795:Enzyme Stability; D006836:Hydro-Lyases / Q000737:chemistry / Q000378:metabolism; D009570:Nitriles / Q000737:chemistry* / Q000378:metabolism; D011549:Pseudomonas / Q000378:metabolism*
C401948:5-cyanovaleramide; D000577:Amides; D009570:Nitriles; D006836:Hydro-Lyases; C048831:nitrile hydratase