Biotransformation of Nitriles by Marine Fungi References 707
Part E | 28
28.19 P. Grunwald: Biocatalysis-Biochemical Fundamentals and Applications (Imperial College Press, London 2009)
28.20 L. Martínkova, V. Kren: Biotransformations with nitrilases, Curr. Opin. Chem. Biol. 14, 130–137 (2010)
28.21 M. Kobayashi, S. Shimizu: Nitrile hydrolases, Curr.
Opin. Chem. Biol. 4, 95–102 (2000)
28.22 T.U. Bornscheuer, R.J. Kazlauskas: Hydrolases in Organic Synthesis (WILEY-VCH, Weinheim 2006)
28.23 I. Endo, M. Okada, M. Yohda: An enzyme controlled
by light: The molecular mechanism of photoreactivity in nitrile hydratase, Trends Biotechnol. 17,
244–248 (1999)
28.24 D. Brady, A. Beeton, J. Zeevaart, C. Kgaje,
E. Rantwijk, R.A. Sheldon: Characterisation of
nitrilase and nitrile hydratase biocatalytic systems, Appl. Microbiol. Biotechnol. 64, 76–85
(2004)
28.25 M. Winkler, A. Glieder, N. Klempier: Enzyme stabilizer DTT catalyzes nitrilase analogue hydrolysis of
nitriles, Chem. Commun. 12, 1298–1300 (2006)
28.26 C.O. Reilly, P.D. Turner: The nitrilases family of
CN hydrolyzing enzymes – A comparative study,
J. Appl. Microbiol. 95, 1161–1174 (2003)
28.27 A. Petrícková, A.B. Veselá, O. Kaplan, D. Kubac,
B. Uhnáková, A. Malandra, J. Felsberg,
A. Rinágelová, P. Weyrauch, V. Kren, K. Bezouska,
L. Martínková: Purification and characterization
of heterologously expressed nitrilases from filamentous fungi, Appl. Microbiol. Biotechnol. 93,
1553–1561 (2012)
28.28 W.-D. Fessner, T. Anthonsen (Eds.): Modern Biocatalysis (Weinheim, Wiley-VCH 2009)
28.29 L. Martínková, V. Vejvoda, V. Kren: Selection
and screening for enzymes of nitrile metabolism,
J. Biotechnol. 133, 318–326 (2008)
28.30 L. Martínková, V. Vejvoda, O. Kaplan, D. Kubac,
A. Malandra, M. Cantarella, K. Bezouska, V. Kren:
Fungal nitrilases as biocatalysts: Recent developments, Biotechnol. Adv. 27, 661–670 (2009)
28.31 O. Kaplan, K. Nikolaou, A. Pisvejcová, L. Martinková: Hydrolysis of nitriles and amides by filamentous fungi, Enzyme Microb. Technol. 38, 260–
264 (2006)
28.32 Y. Asano, Y. Tani, H. Yamada: A new enzyme Nitrile
Hydratase which degrades acetonitrile in combination with amidases, Agric. Biol. Chem. 44, 2251–
2252 (1980)
28.33 D. Fournand, A. Arnaud: Aliphatic and enantioselective amidases: From hydrolysis to acyl transfer
activity, J. Appl. Microbiol. 91, 381–393 (2001)
28.34 R.N. Thuku, D. Brady, M.J. Benedik, B.T. Sewell:
Microbial nitrilases: Versatile, spiral forming, industrial enzymes, J. Appl. Microbiol. 106, 703–727
(2009)
28.35 K. Yamamoto, Y. Ueno, K. Otsubo, K. Kawakami,
K. Komatsu: Production of S-(C)-Ibuprofen from a
nitrile compound by Acinetobacter sp. strain AK226,
Appl. Environ. Microbiol. 56, 3125–3129 (1990)
28.36 P.O. Carvalho, S.A. Calafatti, M. Marassi, D.M. Silva,
F.J. Contesini, R. Bizaco: Potencial de biocatálise
enantiosseletiva de lipases microbianas, Quim.
Nova 28, 614–621 (2005)
28.37 Y.C. He, J.H. Xu, Y. Xu, L.M. Ouyang, J. Pan:
Biocatalytic synthesis of (R)-(-)-mandelic acid
from racemic mandelonitrile by a newly isolated
nitrilase-producer Alcaligenes sp. ECU0401, Chin.
Chem. Lett. 18, 677–680 (2007)
28.38 Y.-P. Xue, Z.-Q. Liu, M. Xu, Y.-J. Wanga, Y.G. Zhenga: Efficient separation of (R/-(-)-mandelic
acid biosynthesized from (R,S)-mandelonitrile by
nitrilase using ion-exchange process, Mar. Drugs 8,
1920–1934 (2010)
28.39 Q.K. Fang, P. Grover, Z. Han, F.X. Mcconville,
R.F. Rossi, D.J. Olsson, D.W. Kessler, S.A. Wald,
C.H. Senanayake: Practical chemical and enzymatic technologies for (S)-1,4-benzodioxan-2carboxypiperizine intermediate in the synthesis of
(S)-doxazosin mesylate, Tetrahedron 12, 2169–2174
(2001)
28.40 N.M. Shaw, K.T. Robins, A. Kiener: Lonza: 20 Years
of Biotransformations, Adv. Synth. Catal. 345, 425
(2003)
28.41 J. Birnbaum, F. Kahan, H. Kropp, J.S. Macdonald: Carbapenems, a new class of betalactam antibiotics – discovery and development
of Imipenen/Cilastatin, Am. J. Med. 78, 3–21
(1985)
28.42 E. Eichhorn, J.P. Roduit, N. Shaw, K. Heinzmann, A. Kiener: Preparation of (S)-piperazine-2carbozylic acid, (R)-piperazine-2-carboxylic acid,
and (S)-piperazine-2-carbozylic acid, by kinetic
resolution of the corresponding racemic carboxamides with stereoselective amidases in whole
bacterial cells, Tetrahedron: Asymm. 8, 2533–2536
(1997)
28.43 H. Nishise, M. Kurihara, Y. Tani: Microbial synthesis of a tranexamic acid intermediate from nitrile,
Agric. Biol. Chem. 51, 2613–2616 (1987)
28.44 S. Bergeron, D.A. Chaplin, J.H. Edwards, B.S.W. Ellis, C.L. Hill, K. Holt-Tiffin, J.R. Knight, T. Mahoney, A.P. Osborne, G. Ruecroft: Nitrilase catalysed desymmetrisation of 3-hydroxyglutaronitrile:
preparation of a statin side-chain intermediate,
Org. Process Res. Dev. 10, 661–665 (2006)
28.45 S.J. Maddrell, N.J. Turner, A. Kerridge, A.J. Willetts,
J. Crosby: Nitrile hidratase enzymes in organic synthesis: Enantioselective synthesis of the lactone
moiety of the mevinic acids, Tetrahedron Lett. 37,
6001–6004 (1996)
28.46 J. Mauger, T. Nagasawa, H. Yamada: Nitrile
hydratase-catalyzed production of isonicotinamide, picolinamide and pyrazinamide from 4cyanopyridine, 2-cyanopyridine and cyanopyrazine in Rhodococcus rhodochrous J1, J. Biotechnol. 8, 87–95 (1988)
28.47 T. Nagasawa, T. Nakamura, H. Yamada: Production of acrylic acid and methacrylic acid using
Part E | 28
28.19 P. Grunwald: Biocatalysis-Biochemical Fundamentals and Applications (Imperial College Press, London 2009)
28.20 L. Martínkova, V. Kren: Biotransformations with nitrilases, Curr. Opin. Chem. Biol. 14, 130–137 (2010)
28.21 M. Kobayashi, S. Shimizu: Nitrile hydrolases, Curr.
Opin. Chem. Biol. 4, 95–102 (2000)
28.22 T.U. Bornscheuer, R.J. Kazlauskas: Hydrolases in Organic Synthesis (WILEY-VCH, Weinheim 2006)
28.23 I. Endo, M. Okada, M. Yohda: An enzyme controlled
by light: The molecular mechanism of photoreactivity in nitrile hydratase, Trends Biotechnol. 17,
244–248 (1999)
28.24 D. Brady, A. Beeton, J. Zeevaart, C. Kgaje,
E. Rantwijk, R.A. Sheldon: Characterisation of
nitrilase and nitrile hydratase biocatalytic systems, Appl. Microbiol. Biotechnol. 64, 76–85
(2004)
28.25 M. Winkler, A. Glieder, N. Klempier: Enzyme stabilizer DTT catalyzes nitrilase analogue hydrolysis of
nitriles, Chem. Commun. 12, 1298–1300 (2006)
28.26 C.O. Reilly, P.D. Turner: The nitrilases family of
CN hydrolyzing enzymes – A comparative study,
J. Appl. Microbiol. 95, 1161–1174 (2003)
28.27 A. Petrícková, A.B. Veselá, O. Kaplan, D. Kubac,
B. Uhnáková, A. Malandra, J. Felsberg,
A. Rinágelová, P. Weyrauch, V. Kren, K. Bezouska,
L. Martínková: Purification and characterization
of heterologously expressed nitrilases from filamentous fungi, Appl. Microbiol. Biotechnol. 93,
1553–1561 (2012)
28.28 W.-D. Fessner, T. Anthonsen (Eds.): Modern Biocatalysis (Weinheim, Wiley-VCH 2009)
28.29 L. Martínková, V. Vejvoda, V. Kren: Selection
and screening for enzymes of nitrile metabolism,
J. Biotechnol. 133, 318–326 (2008)
28.30 L. Martínková, V. Vejvoda, O. Kaplan, D. Kubac,
A. Malandra, M. Cantarella, K. Bezouska, V. Kren:
Fungal nitrilases as biocatalysts: Recent developments, Biotechnol. Adv. 27, 661–670 (2009)
28.31 O. Kaplan, K. Nikolaou, A. Pisvejcová, L. Martinková: Hydrolysis of nitriles and amides by filamentous fungi, Enzyme Microb. Technol. 38, 260–
264 (2006)
28.32 Y. Asano, Y. Tani, H. Yamada: A new enzyme Nitrile
Hydratase which degrades acetonitrile in combination with amidases, Agric. Biol. Chem. 44, 2251–
2252 (1980)
28.33 D. Fournand, A. Arnaud: Aliphatic and enantioselective amidases: From hydrolysis to acyl transfer
activity, J. Appl. Microbiol. 91, 381–393 (2001)
28.34 R.N. Thuku, D. Brady, M.J. Benedik, B.T. Sewell:
Microbial nitrilases: Versatile, spiral forming, industrial enzymes, J. Appl. Microbiol. 106, 703–727
(2009)
28.35 K. Yamamoto, Y. Ueno, K. Otsubo, K. Kawakami,
K. Komatsu: Production of S-(C)-Ibuprofen from a
nitrile compound by Acinetobacter sp. strain AK226,
Appl. Environ. Microbiol. 56, 3125–3129 (1990)
28.36 P.O. Carvalho, S.A. Calafatti, M. Marassi, D.M. Silva,
F.J. Contesini, R. Bizaco: Potencial de biocatálise
enantiosseletiva de lipases microbianas, Quim.
Nova 28, 614–621 (2005)
28.37 Y.C. He, J.H. Xu, Y. Xu, L.M. Ouyang, J. Pan:
Biocatalytic synthesis of (R)-(-)-mandelic acid
from racemic mandelonitrile by a newly isolated
nitrilase-producer Alcaligenes sp. ECU0401, Chin.
Chem. Lett. 18, 677–680 (2007)
28.38 Y.-P. Xue, Z.-Q. Liu, M. Xu, Y.-J. Wanga, Y.G. Zhenga: Efficient separation of (R/-(-)-mandelic
acid biosynthesized from (R,S)-mandelonitrile by
nitrilase using ion-exchange process, Mar. Drugs 8,
1920–1934 (2010)
28.39 Q.K. Fang, P. Grover, Z. Han, F.X. Mcconville,
R.F. Rossi, D.J. Olsson, D.W. Kessler, S.A. Wald,
C.H. Senanayake: Practical chemical and enzymatic technologies for (S)-1,4-benzodioxan-2carboxypiperizine intermediate in the synthesis of
(S)-doxazosin mesylate, Tetrahedron 12, 2169–2174
(2001)
28.40 N.M. Shaw, K.T. Robins, A. Kiener: Lonza: 20 Years
of Biotransformations, Adv. Synth. Catal. 345, 425
(2003)
28.41 J. Birnbaum, F. Kahan, H. Kropp, J.S. Macdonald: Carbapenems, a new class of betalactam antibiotics – discovery and development
of Imipenen/Cilastatin, Am. J. Med. 78, 3–21
(1985)
28.42 E. Eichhorn, J.P. Roduit, N. Shaw, K. Heinzmann, A. Kiener: Preparation of (S)-piperazine-2carbozylic acid, (R)-piperazine-2-carboxylic acid,
and (S)-piperazine-2-carbozylic acid, by kinetic
resolution of the corresponding racemic carboxamides with stereoselective amidases in whole
bacterial cells, Tetrahedron: Asymm. 8, 2533–2536
(1997)
28.43 H. Nishise, M. Kurihara, Y. Tani: Microbial synthesis of a tranexamic acid intermediate from nitrile,
Agric. Biol. Chem. 51, 2613–2616 (1987)
28.44 S. Bergeron, D.A. Chaplin, J.H. Edwards, B.S.W. Ellis, C.L. Hill, K. Holt-Tiffin, J.R. Knight, T. Mahoney, A.P. Osborne, G. Ruecroft: Nitrilase catalysed desymmetrisation of 3-hydroxyglutaronitrile:
preparation of a statin side-chain intermediate,
Org. Process Res. Dev. 10, 661–665 (2006)
28.45 S.J. Maddrell, N.J. Turner, A. Kerridge, A.J. Willetts,
J. Crosby: Nitrile hidratase enzymes in organic synthesis: Enantioselective synthesis of the lactone
moiety of the mevinic acids, Tetrahedron Lett. 37,
6001–6004 (1996)
28.46 J. Mauger, T. Nagasawa, H. Yamada: Nitrile
hydratase-catalyzed production of isonicotinamide, picolinamide and pyrazinamide from 4cyanopyridine, 2-cyanopyridine and cyanopyrazine in Rhodococcus rhodochrous J1, J. Biotechnol. 8, 87–95 (1988)
28.47 T. Nagasawa, T. Nakamura, H. Yamada: Production of acrylic acid and methacrylic acid using