Protein Information

Name nitrilase (protein family or complex)
Synonyms Nitrilase; Nitrilases

Compound Information

Name acrylonitrile
CAS 2-propenenitrile

Reference List

PubMed Abstract RScore(About this table)
19430115 Nigam VK, Khandelwal AK, Gothwal RK, Mohan MK, Choudhury B, Vidyarthi AS, Ghosh P: Nitrilase-catalysed conversion of acrylonitrile by free and immobilized cells of Streptomyces sp. J Biosci. 2009 Mar;34(1):21-6.
87(1,1,2,2) Details
10068794 Hughes J, Armitage YC, Symes KC: Application of whole cell rhodococcal biocatalysts in acrylic polymer manufacture. Antonie Van Leeuwenhoek. 1998 Jul-Oct;74(1-3):107-18.

The use of biocatalysts in the chemical industry has in the main been for the manufacture of high-value fine chemicals, such as pharmaceutical intermediates, though investigations into the use of nitrile hydratase, amidase and nitrilase to convert acrylonitrile into the higher value products acrylamide and acrylic acid have been carried out for a number of years.
81(1,1,1,1) Details
1390687 Kobayashi M, Yanaka N, Nagasawa T, Yamada H: Primary structure of an aliphatic nitrile-degrading enzyme, aliphatic nitrilase, from Rhodococcus rhodochrous K22 and expression of its gene and identification of its active site residue. Biochemistry. 1992 Sep 22;31(37):9000-7.

Peptides obtained by cleavage of a Rhodococcus rhodochrous K22 nitrilase, which acts on aliphatic nitriles such as acrylonitrile, crotonitrile, and glutaronitrile, have been sequenced.
40(0,1,1,10) Details
17544472 Li T, Liu J, Bai R, Ohandja DG, Wong FS: Biodegradation of organonitriles by adapted activated sludge consortium with acetonitrile-degrading microorganisms. Water Res. 2007 Aug;41(15):3465-73. Epub 2007 May 8.

The results suggest that, depending on the substrates, the adapted mixed culture can develop very different degradation pathways, such as nitrile hydratase plus amidase for acetonitrile or acrylonitrile and nitrilase for benzonitrile.
31(0,1,1,1) Details
19597316 Shen M, Zheng YG, Liu ZQ, Shen YC: Production of acrylic acid from Acrylonitrile by immobilization of Arthrobacter nitroguajacolicus ZJUTB06-99. J Microbiol Biotechnol. 2009 Jun;19(6):582-7.

Immobilized cells of Arthrobacter nitroguajacolicus ZJUTB06-99 capable of producing nitrilase was used for biotransformation of acrylonitrile to acrylic acid.
7(0,0,1,2) Details
18795282 Chmura A, Shapovalova AA, van Pelt S, van Rantwijk F, Tourova TP, Muyzer G, Sorokin DY: Utilization of arylaliphatic nitriles by haloalkaliphilic Halomonas nitrilicus sp. nov. isolated from soda soils. Appl Microbiol Biotechnol. 2008 Nov;81(2):371-8. Epub 2008 Sep 16.

Apart from the nitriles mentioned above, resting cells of ANL-alpha CH3 also hydrolyzed mandelonitrile, benzonitrile, acrylonitrile, and phenylglycinonitrile, presumably using nitrilase pathway.
6(0,0,1,1) Details
2394676 Kobayashi M, Yanaka N, Nagasawa T, Yamada H: Purification and characterization of a novel nitrilase of Rhodococcus rhodochrous K22 that acts on aliphatic nitriles. J Bacteriol. 1990 Sep;172(9):4807-15.

The enzyme acted on aliphatic olefinic nitriles such as crotononitrile and acrylonitrile as the most suitable substrates.
5(0,0,0,5) Details
10978771 Kim S, Oriel P: Cloning and expression of the nitrile hydratase and amidase genes from Bacillus sp. Enzyme Microb Technol. 2000 Oct 1;27(7):492-501.

BR449 was previously shown to exhibit a high level of nitrile hydratase (NHase) activity when growing on high levels of acrylonitrile at 55 degrees C.
Analysis of deduced amino acid sequences indicate that the amidase (348 aa, MW 38.6 kDa) belongs to the nitrilase-related aliphatic amidase family, and that the NHase beta- (229 aa, MW 26.5 kDa) and alpha- (214 aa, MW 24.5 kDa) subunits comprise a cobalt-containing member of the NHase family, which includes Rhodococcus rhodochrous J1 and Pseudomonas putida 5B NHases.
1(0,0,0,1) Details
10601860 Nagasawa T, Wieser M, Nakamura T, Iwahara H, Yoshida T, Gekko K: Nitrilase of Rhodococcus rhodochrous J1. Eur J Biochem. 2000 Jan;267(1):138-44.

Nitrilase-containing resting cells of Rhodococcus rhodochrous J1 converted acrylonitrile and benzonitrile to the corresponding acids, but the purified nitrilase hydrolyzed only benzonitrile, and not acrylonitrile.
1(0,0,0,1) Details
19287539 Rustler S, Chmura A, Sheldon RA, Stolz A: Characterisation of the substrate specificity of the nitrile hydrolyzing system of the acidotolerant black yeast Exophiala oligosperma R1. Stud Mycol. 2008;61:165-74.

It was therefore concluded that the cells harboured a nitrilase activity.
Aliphatic substrates such as acrylonitrile and 2-hydroxy-3-butenenitrile were also hydrolysed.
1(0,0,0,1) Details
10068792 Bunch AW: Biotransformation of nitriles by rhodococci. Antonie Van Leeuwenhoek. 1998 Jul-Oct;74(1-3):89-97.


This in turn has resulted in some truly remarkable biotransformation activities being obtained, which have been successfully exploited for commercial organic syntheses (e.g. acrylamide production from acrylonitrile).
0(0,0,0,0) Details