Selective hydrolysis of the nitrile group of cis-dihydrodiols from aromatic nitriles

Yildirim, Selçuk; Ruinatscha, Reto; Gross, Rainer; Wohlgemuth, Roland; Kohler, Hans-Peter E.; Witholt, Bernard; Schmid, Andreas

doi:10.1016/j.molcatb.2005.11.006

Publication type:	Article in scientific journal
Type of review:	Peer review (publication)
Title:	Selective hydrolysis of the nitrile group of cis-dihydrodiols from aromatic nitriles
Authors:	Yildirim, Selçuk Ruinatscha, Reto Gross, Rainer Wohlgemuth, Roland Kohler, Hans-Peter E. Witholt, Bernard Schmid, Andreas
DOI:	10.1016/j.molcatb.2005.11.006
Published in:	Journal of Molecular Catalysis B: Enzymatic
Volume(Issue):	38
Issue:	2
Page(s):	76
Pages to:	83
Issue Date:	Feb-2006
Publisher / Ed. Institution:	Elsevier
ISSN:	1381-1177
Language:	English
Subjects:	Dihydrodiol; Nitrile; Enzyme; Biocatalysis
Subject (DDC):	572: Biochemistry 660.6: Biotechnology
Abstract:	Several nitrilases were screened for the hydrolysis of the nitrile group of cis-1,2-dihydroxy-3-cyanocyclohexa-3,5-diene and trans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylonitrile to the corresponding acids. Nitrilase from Rhodococcus sp. was able to convert both compounds with the activity of 0.3 mU/mg protein and 0.05 mU/mg protein, respectively. Nitrilase AtNIT1 from Arabidopsis thaliana converted only the latter but with a higher initial specific activity of 1.7 mU/mg protein. Biotransformation of trans-3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dienyl]-acrylonitrile was performed with AtNIT1 in the form of isolated enzyme and immobilized enzyme, and with recombinant cells containing AtNIT1. Biotransformations with isolated AtNIT1 resulted in 116 mg of product in 10.6 h with a yield of 77%. Forty-three percent of the enzymatic activity could be recovered after the biotransformation. Immobilization of AtNIT1 saturated with 3-phenylpropionitrile resulted in 3.5% of the free enzyme activity. Biotransformations with Escherischia coli JM101 (pQE10-AtNIT1) in shake-flasks produced 243 mg of product in 23 h with a yield of 48%. Maximum and average specific activities of 0.5 U/g cell dry weight and 0.17 U/g cell dry weight were achieved, respectively.
URI:	https://digitalcollection.zhaw.ch/handle/11475/7074
Fulltext version:	Published version
License (according to publishing contract):	Licence according to publishing contract
Departement:	Life Sciences and Facility Management
Organisational Unit:	Institute of Food and Beverage Innovation (ILGI)
Appears in collections:	Publikationen Life Sciences und Facility Management

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Yildirim, S., Ruinatscha, R., Gross, R., Wohlgemuth, R., Kohler, H.-P. E., Witholt, B., & Schmid, A. (2006). Selective hydrolysis of the nitrile group of cis-dihydrodiols from aromatic nitriles. Journal of Molecular Catalysis B: Enzymatic, 38(2), 76–83. https://doi.org/10.1016/j.molcatb.2005.11.006

Yildirim, S. et al. (2006) ‘Selective hydrolysis of the nitrile group of cis-dihydrodiols from aromatic nitriles’, Journal of Molecular Catalysis B: Enzymatic, 38(2), pp. 76–83. Available at: https://doi.org/10.1016/j.molcatb.2005.11.006.

S. Yildirim et al., “Selective hydrolysis of the nitrile group of cis-dihydrodiols from aromatic nitriles,” Journal of Molecular Catalysis B: Enzymatic, vol. 38, no. 2, pp. 76–83, Feb. 2006, doi: 10.1016/j.molcatb.2005.11.006.

YILDIRIM, Selçuk, Reto RUINATSCHA, Rainer GROSS, Roland WOHLGEMUTH, Hans-Peter E. KOHLER, Bernard WITHOLT und Andreas SCHMID, 2006. Selective hydrolysis of the nitrile group of cis-dihydrodiols from aromatic nitriles. Journal of Molecular Catalysis B: Enzymatic. Februar 2006. Bd. 38, Nr. 2, S. 76–83. DOI 10.1016/j.molcatb.2005.11.006

Yildirim, Selçuk, Reto Ruinatscha, Rainer Gross, Roland Wohlgemuth, Hans-Peter E. Kohler, Bernard Witholt, and Andreas Schmid. 2006. “Selective Hydrolysis of the Nitrile Group of Cis-Dihydrodiols from Aromatic Nitriles.” Journal of Molecular Catalysis B: Enzymatic 38 (2): 76–83. https://doi.org/10.1016/j.molcatb.2005.11.006.

Yildirim, Selçuk, et al. “Selective Hydrolysis of the Nitrile Group of Cis-Dihydrodiols from Aromatic Nitriles.” Journal of Molecular Catalysis B: Enzymatic, vol. 38, no. 2, Feb. 2006, pp. 76–83, https://doi.org/10.1016/j.molcatb.2005.11.006.