Literature DB >> 10579532

5-Cyanovaleramide production using immobilized Pseudomonas chlororaphis B23.

E C Hann1, A Eisenberg, S K Fager, N E Perkins, F G Gallagher, S M Cooper, J E Gavagan, B Stieglitz, S M Hennessey, R DiCosimo.   

Abstract

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).

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Year:  1999        PMID: 10579532     DOI: 10.1016/s0968-0896(99)00157-1

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  7 in total

1.  Crystal structure of aldoxime dehydratase and its catalytic mechanism involved in carbon-nitrogen triple-bond synthesis.

Authors:  Junpei Nomura; Hiroshi Hashimoto; Takehiro Ohta; Yoshiteru Hashimoto; Koichi Wada; Yoshinori Naruta; Ken-Ichi Oinuma; Michihiko Kobayashi
Journal:  Proc Natl Acad Sci U S A       Date:  2013-02-04       Impact factor: 11.205

2.  Discovery of a reaction intermediate of aliphatic aldoxime dehydratase involving heme as an active center.

Authors:  Kazunobu Konishi; Takehiro Ohta; Ken-Ichi Oinuma; Yoshiteru Hashimoto; Teizo Kitagawa; Michihiko Kobayashi
Journal:  Proc Natl Acad Sci U S A       Date:  2006-01-06       Impact factor: 11.205

3.  Transcriptional regulation of the nitrile hydratase gene cluster in Pseudomonas chlororaphis B23.

Authors:  Toshihide Sakashita; Yoshiteru Hashimoto; Ken-ichi Oinuma; Michihiko Kobayashi
Journal:  J Bacteriol       Date:  2008-04-11       Impact factor: 3.490

4.  Characterization of a nitrilase and a nitrile hydratase from Pseudomonas sp. strain UW4 that converts indole-3-acetonitrile to indole-3-acetic acid.

Authors:  Daiana Duca; David R Rose; Bernard R Glick
Journal:  Appl Environ Microbiol       Date:  2014-08       Impact factor: 4.792

Review 5.  Strategies for discovery and improvement of enzyme function: state of the art and opportunities.

Authors:  Praveen Kaul; Yasuhisa Asano
Journal:  Microb Biotechnol       Date:  2011-08-24       Impact factor: 5.813

6.  Substrate Profiling of the Cobalt Nitrile Hydratase from Rhodococcus rhodochrous ATCC BAA 870.

Authors:  Adelaide R Mashweu; Varsha P Chhiba-Govindjee; Moira L Bode; Dean Brady
Journal:  Molecules       Date:  2020-01-06       Impact factor: 4.411

Review 7.  The Hitchhiker's guide to biocatalysis: recent advances in the use of enzymes in organic synthesis.

Authors:  Roger A Sheldon; Dean Brady; Moira L Bode
Journal:  Chem Sci       Date:  2020-02-13       Impact factor: 9.825

  7 in total

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