Literature DB >> 11826962

High yield synthesis of nitriles by a new enzyme, phenylacetaldoxime dehydratase, from Bacillus sp. strain OxB-1.

S X Xie1, Y Kato, Y Asano.   

Abstract

3-Phenylpropionitrile was synthesized from Z-3-phenylpropionaldoxime (0.75 M) in a quantitative yield (98 g/l) by the use of cells of Escherichia coli JM 109/pOxD-90F, a transformant harboring a gene for a new enzyme, phenylacetaldoxime dehydratase, from Bacillus sp. strain OxB-1. Other arylalkyl- and alkyl-nitriles were also synthesized in high yields from the corresponding aldoximes. Moreover, 3-phenylpropionitrile was successfully synthesized by the recombinant cells in 70 and 100% yields from 0.1 M unpurified E/Z-3-phenylpropionaldoxime, which is spontaneously formed from 3-phenylpropionaldehyde and hydroxylamine in a butyl acetate/water biphasic system and aqueous phase, respectively.

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Year:  2001        PMID: 11826962     DOI: 10.1271/bbb.65.2666

Source DB:  PubMed          Journal:  Biosci Biotechnol Biochem        ISSN: 0916-8451            Impact factor:   2.043


  8 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.  Biosynthetic pathway for the cyanide-free production of phenylacetonitrile in Escherichia coli by utilizing plant cytochrome P450 79A2 and bacterial aldoxime dehydratase.

Authors:  Yuta Miki; Yasuhisa Asano
Journal:  Appl Environ Microbiol       Date:  2014-08-29       Impact factor: 4.792

4.  Complete Genome Sequence of an Aldoxime Degrader, Bacillus sp. OxB-1.

Authors:  Takuya Yamaguchi; Yasuhisa Asano
Journal:  Genome Announc       Date:  2015-02-26

5.  Catalytic Promiscuity of Galactose Oxidase: A Mild Synthesis of Nitriles from Alcohols, Air, and Ammonia.

Authors:  Jan Vilím; Tanja Knaus; Francesco G Mutti
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-08       Impact factor: 15.336

6.  Biocatalytic production of adiponitrile and related aliphatic linear α,ω-dinitriles.

Authors:  Tobias Betke; Manuel Maier; Heidrun Gruber-Wölfler; Harald Gröger
Journal:  Nat Commun       Date:  2018-11-30       Impact factor: 14.919

7.  Genomic analyses of Burkholderia cenocepacia reveal multiple species with differential host-adaptation to plants and humans.

Authors:  Adrian Wallner; Eoghan King; Eddy L M Ngonkeu; Lionel Moulin; Gilles Béna
Journal:  BMC Genomics       Date:  2019-11-04       Impact factor: 3.969

8.  Synthetic Processes toward Nitriles without the Use of Cyanide: A Biocatalytic Concept Based on Dehydration of Aldoximes in Water.

Authors:  Alessa Hinzmann; Tobias Betke; Yasuhisa Asano; Harald Gröger
Journal:  Chemistry       Date:  2021-01-22       Impact factor: 5.236

  8 in total

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