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Volumn 105, Issue 4, 2008, Pages 1150-1157

R-enantioselective hydrolysis of 2,2-dimethylcyclopropanecarboxamide by amidase from a newly isolated strain Brevibacterium epidermidis ZJB-07021

Author keywords

2,2 dimethylcyclopropanecarboxamide; Amidase; Brevibacterium epidermidis; Enantioselective synthesis; Temperature

Indexed keywords

BIOCONVERSION; ENANTIOSELECTIVITY; ENZYMES; RNA;

EID: 52049110296     PISSN: 13645072     EISSN: 13652672     Source Type: Journal    
DOI: 10.1111/j.1365-2672.2008.03841.x     Document Type: Article
Times cited : (20)

References (40)
  • 2
    • 0037413411 scopus 로고    scopus 로고
    • New thermostable d-methionine amidase from Brevibacillus borstelensis BCS-1 and its application for d-phenylalanine production
    • Baek, D.H., Song, J.J., Lee, S.G., Kwon, S.J., Asano, Y. Sung, M.H. (2003) New thermostable d-methionine amidase from Brevibacillus borstelensis BCS-1 and its application for d-phenylalanine production. Enzyme Microb Technol 32, 131 139.
    • (2003) Enzyme Microb Technol , vol.32 , pp. 131-139
    • Baek, D.H.1    Song, J.J.2    Lee, S.G.3    Kwon, S.J.4    Asano, Y.5    Sung, M.H.6
  • 3
    • 0037209758 scopus 로고    scopus 로고
    • The nitrile-degrading enzymes: Current status and future prospects
    • Banerjee, A., Sharma, R. Banerjee, U.C. (2002) The nitrile-degrading enzymes: current status and future prospects. Appl Microbiol Biotechnol 60, 33 44.
    • (2002) Appl Microbiol Biotechnol , vol.60 , pp. 33-44
    • Banerjee, A.1    Sharma, R.2    Banerjee, U.C.3
  • 5
    • 0029121266 scopus 로고
    • Selective enzymatic-hydrolysis of aromatic diesters using esterase from Brevibacterium imperiale B222
    • Bianchi, D., Bortolo, R., Bernardi, A., Gagliardi, I. Ingrassia, A.G.M. (1995) Selective enzymatic-hydrolysis of aromatic diesters using esterase from Brevibacterium imperiale B222. Biotechnol Lett 17, 711 716.
    • (1995) Biotechnol Lett , vol.17 , pp. 711-716
    • Bianchi, D.1    Bortolo, R.2    Bernardi, A.3    Gagliardi, I.4    Ingrassia, A.G.M.5
  • 6
    • 0021798830 scopus 로고
    • Carbapenems, a new class of beta-lactam antibiotics: Discovery and development of imipenem/cilastatin
    • Birnbaum, J., Kahan, F.M., Kropp, H. Macdonald, J.S. (1985) Carbapenems, a new class of beta-lactam antibiotics: discovery and development of imipenem/cilastatin. Am J Med 78, 3 21.
    • (1985) Am J Med , vol.78 , pp. 3-21
    • Birnbaum, J.1    Kahan, F.M.2    Kropp, H.3    MacDonald, J.S.4
  • 7
    • 27844483915 scopus 로고    scopus 로고
    • Use of a UF-membrane reactor for controlling selectively the nitrile hydratase-amidase system in Microbacterium imperiale CBS 498-74 resting cells case study: Benzonitrile conversion
    • Cantarella, M., Cantarella, L., Gallifuoco, A. Spera, A. (2006) Use of a UF-membrane reactor for controlling selectively the nitrile hydratase-amidase system in Microbacterium imperiale CBS 498-74 resting cells case study: benzonitrile conversion. Enzyme Microb Technol 38, 126 134.
    • (2006) Enzyme Microb Technol , vol.38 , pp. 126-134
    • Cantarella, M.1    Cantarella, L.2    Gallifuoco, A.3    Spera, A.4
  • 8
    • 0035828834 scopus 로고    scopus 로고
    • Synthesis of cyclopropane containing natural products
    • Donaldson, W.A. (2001) Synthesis of cyclopropane containing natural products. Tetrahedron 57, 8589 8627.
    • (2001) Tetrahedron , vol.57 , pp. 8589-8627
    • Donaldson, W.A.1
  • 9
    • 0032500082 scopus 로고    scopus 로고
    • New aspects of catalytic asymmetric cyclopropanation
    • Doyle, M.P. Protopopova, M.N. (1998) New aspects of catalytic asymmetric cyclopropanation. Tetrahedron 54, 7919 7946.
    • (1998) Tetrahedron , vol.54 , pp. 7919-7946
    • Doyle, M.P.1    Protopopova, M.N.2
  • 10
    • 0030790662 scopus 로고    scopus 로고
    • Preparation of (S)-piperazine-2-carboxylic acid, (R)-piperazine-2- carboxylic acid, and (S)-piperidine-2-carboxylic acid by kinetic resolution of the corresponding racemic carboxamides with stereoselective amidases in whole bacterial cells
    • Eichhorn, E., Roduit, J.P., Shaw, N., Heinzmann, K. Kiener, A. (1997) Preparation of (S)-piperazine-2-carboxylic acid, (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid by kinetic resolution of the corresponding racemic carboxamides with stereoselective amidases in whole bacterial cells. Tetrahedron Asymmetry 8, 2533 2536.
    • (1997) Tetrahedron Asymmetry , vol.8 , pp. 2533-2536
    • Eichhorn, E.1    Roduit, J.P.2    Shaw, N.3    Heinzmann, K.4    Kiener, A.5
  • 11
    • 0000461280 scopus 로고
    • Confidence limits on phylogenies: An approach using the Bootstrap
    • Felsenstein, J. (1985) Confidence limits on phylogenies: an approach using the Bootstrap. Evolution 39, 783 791.
    • (1985) Evolution , vol.39 , pp. 783-791
    • Felsenstein, J.1
  • 12
    • 0035723343 scopus 로고    scopus 로고
    • Aliphatic and enantioselective amidases: From hydrolysis to acyl transfer activity
    • Fournand, D. Arnaud, A. (2001) Aliphatic and enantioselective amidases: from hydrolysis to acyl transfer activity. J Appl Microbiol 91, 381 393.
    • (2001) J Appl Microbiol , vol.91 , pp. 381-393
    • Fournand, D.1    Arnaud, A.2
  • 14
    • 34248594473 scopus 로고    scopus 로고
    • Isolation of glycolonitrile-hydrolyzing microorganism based on colorimetric reaction
    • Hu, J.G., Wang, Y.J., Zheng, Y.G. Shen, Y.C. (2007) Isolation of glycolonitrile-hydrolyzing microorganism based on colorimetric reaction. Enzyme Microb Technol 41, 244 249.
    • (2007) Enzyme Microb Technol , vol.41 , pp. 244-249
    • Hu, J.G.1    Wang, Y.J.2    Zheng, Y.G.3    Shen, Y.C.4
  • 16
    • 0019296687 scopus 로고
    • A simple method for estimating evolutionary rates of base substitutions through comparative studies of nucleotide sequences
    • Kimura, M. (1980) A simple method for estimating evolutionary rates of base substitutions through comparative studies of nucleotide sequences. J Mol Evol 16, 111 120.
    • (1980) J Mol Evol , vol.16 , pp. 111-120
    • Kimura, M.1
  • 17
    • 0034067403 scopus 로고    scopus 로고
    • Gene cloning, nucleotide sequencing, and purification and characterization of the d-stereospecific amino-acid amidase from Ochrobactrum anthropi SV3
    • Komeda, H. Asano, Y. (2000) Gene cloning, nucleotide sequencing, and purification and characterization of the d-stereospecific amino-acid amidase from Ochrobactrum anthropi SV3. Eur J Biochem 267, 2028 2035.
    • (2000) Eur J Biochem , vol.267 , pp. 2028-2035
    • Komeda, H.1    Asano, Y.2
  • 18
    • 2142757279 scopus 로고    scopus 로고
    • A novel R-stereoselective amidase from Pseudomonas sp MCI3434 acting on piperazine-2-tert-butylcarboxamide
    • Komeda, H., Harada, H., Washika, S., Sakamoto, T., Ueda, M. Asano, Y. (2004) A novel R-stereoselective amidase from Pseudomonas sp MCI3434 acting on piperazine-2-tert-butylcarboxamide. Eur J Biochem 271, 1580 1590.
    • (2004) Eur J Biochem , vol.271 , pp. 1580-1590
    • Komeda, H.1    Harada, H.2    Washika, S.3    Sakamoto, T.4    Ueda, M.5    Asano, Y.6
  • 19
    • 0346007406 scopus 로고    scopus 로고
    • Screening for amidases: Isolation and characterization of a novel D-amidase from Variovorax paradoxus
    • Krieg, L., Ansorge-Schumacher, M.B. Kula, M.R. (2002) Screening for amidases: isolation and characterization of a novel D-amidase from Variovorax paradoxus. Adv Synth Catal 344, 965 973.
    • (2002) Adv Synth Catal , vol.344 , pp. 965-973
    • Krieg, L.1    Ansorge-Schumacher, M.B.2    Kula, M.R.3
  • 20
    • 0036139211 scopus 로고    scopus 로고
    • MEGA2: Molecular evolutionary genetics analysis software
    • Kumar, S., Tamura, K., Jakobsen, I.B. Nei, M. (2001) MEGA2: molecular evolutionary genetics analysis software. Bioinformatics 17, 1244 1245.
    • (2001) Bioinformatics , vol.17 , pp. 1244-1245
    • Kumar, S.1    Tamura, K.2    Jakobsen, I.B.3    Nei, M.4
  • 21
    • 0035910863 scopus 로고    scopus 로고
    • Enantioselective enzyme catalysed ammoniolysis of amino acid derivatives. Effect of temperature
    • López-Serrano, P., Wegman, M.A., van Rantwijk, F. Sheldon, R.A. (2001) Enantioselective enzyme catalysed ammoniolysis of amino acid derivatives. Effect of temperature. Tetrahedron Asymmetry 12, 235 240.
    • (2001) Tetrahedron Asymmetry , vol.12 , pp. 235-240
    • López-Serrano, P.1    Wegman, M.A.2    Van Rantwijk, F.3    Sheldon, R.A.4
  • 23
    • 0036228279 scopus 로고    scopus 로고
    • Nitrile- and amide-converting microbial enzymes: Stereo-, regio- and chemoselectivity
    • Martinkova, L. Kren, V. (2002) Nitrile- and amide-converting microbial enzymes: stereo-, regio- and chemoselectivity. Biocatal Biotransform 20, 73 93.
    • (2002) Biocatal Biotransform , vol.20 , pp. 73-93
    • Martinkova, L.1    Kren, V.2
  • 24
    • 0025604503 scopus 로고
    • Purification, cloning, and primary structure of an enantiomer-selective amidase from Brevibacterium sp. strain R312: Structural evidence for genetic coupling with nitrile hydratase
    • Mayaux, J.F., Cerebelaud, E., Soubrier, F., Faucher, D. Petre, D. (1990) Purification, cloning, and primary structure of an enantiomer-selective amidase from Brevibacterium sp. strain R312: structural evidence for genetic coupling with nitrile hydratase. J Bacteriol 172, 6764 6773.
    • (1990) J Bacteriol , vol.172 , pp. 6764-6773
    • Mayaux, J.F.1    Cerebelaud, E.2    Soubrier, F.3    Faucher, D.4    Petre, D.5
  • 25
    • 0034848412 scopus 로고    scopus 로고
    • Rational design of enantioselective enzymes requires considerations of entropy
    • Oattosson, J., Rotticci-Mulder, J.C., Rotticci, D. Hult, K. (2001) Rational design of enantioselective enzymes requires considerations of entropy. Protein Sci 10, 1769 1774.
    • (2001) Protein Sci , vol.10 , pp. 1769-1774
    • Oattosson, J.1    Rotticci-Mulder, J.C.2    Rotticci, D.3    Hult, K.4
  • 26
    • 0000536380 scopus 로고
    • Enzymatic production of D-alanine from DL-alaninamide by novel D-alaninamide specific amide hydrolase
    • Ozaki, A., Kawasaki, H., Yagasaki, M. Hashimoto, Y. (1992) Enzymatic production of D-alanine from DL-alaninamide by novel D-alaninamide specific amide hydrolase. Biosci Biotechnol Biochem 56, 1980 1984.
    • (1992) Biosci Biotechnol Biochem , vol.56 , pp. 1980-1984
    • Ozaki, A.1    Kawasaki, H.2    Yagasaki, M.3    Hashimoto, Y.4
  • 28
    • 0030066698 scopus 로고    scopus 로고
    • Temperature modulation of the stereochemistry of enzymatic catalysis: Prospects for exploitation
    • Phillips, R.S. (1996) Temperature modulation of the stereochemistry of enzymatic catalysis: prospects for exploitation. Trends Biotechnol 14, 13 16.
    • (1996) Trends Biotechnol , vol.14 , pp. 13-16
    • Phillips, R.S.1
  • 29
    • 0027897680 scopus 로고
    • A simple method to determine the enantiomeric ratio in enantioselective biocatalysis
    • Rakels, J.L.L., Straathof, A.J.J. Heijnen, J.J. (1993) A simple method to determine the enantiomeric ratio in enantioselective biocatalysis. Enzym Microb Technol 15, 1051 1056.
    • (1993) Enzym Microb Technol , vol.15 , pp. 1051-1056
    • Rakels, J.L.L.1    Straathof, A.J.J.2    Heijnen, J.J.3
  • 30
    • 4644222088 scopus 로고    scopus 로고
    • 'Low-temperature method' for a dramatic improvement in enantioselectivity in lipase-catalyzed reactions
    • Sakai, T. (2004) 'Low-temperature method' for a dramatic improvement in enantioselectivity in lipase-catalyzed reactions. Tetrahedron Asymmetry 15, 2749 2756.
    • (2004) Tetrahedron Asymmetry , vol.15 , pp. 2749-2756
    • Sakai, T.1
  • 31
    • 0036328455 scopus 로고    scopus 로고
    • Selection, purification, characterisation, and cloning of a novel heat-stable stereo-specific amidase from Klebsiella oxytoca, and its application in the synthesis of enantiomerically pure (R)- and (S)-3,3,3-trifluoro-2- hydroxy-2-methylpropionic acids and (S)-3,3,3-trifluoro-2-hydroxy-2- methylpropionamide
    • Shaw, N.M., Naughton, A., Robins, K., Tinschert, A., Schmid, E., Hischier, M.L., Venetz, V., Werlen, J. et al. (2002) Selection, purification, characterisation, and cloning of a novel heat-stable stereo-specific amidase from Klebsiella oxytoca, and its application in the synthesis of enantiomerically pure (R)- and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionic acids and (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide. Org Process Res Dev 6, 497 504.
    • (2002) Org Process Res Dev , vol.6 , pp. 497-504
    • Shaw, N.M.1    Naughton, A.2    Robins, K.3    Tinschert, A.4    Schmid, E.5    Hischier, M.L.6    Venetz, V.7    Werlen, J.8
  • 32
    • 0242438894 scopus 로고    scopus 로고
    • Lonza: 20 years of biotransformations
    • Shaw, N.M., Robins, K.T. Kiener, A. (2003) Lonza: 20 years of biotransformations. Adv Synth Catal 345, 425 435.
    • (2003) Adv Synth Catal , vol.345 , pp. 425-435
    • Shaw, N.M.1    Robins, K.T.2    Kiener, A.3
  • 33
    • 0027968068 scopus 로고
    • Clustal W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice
    • Thompson, J.D., Higgins, D.G. Gibson, T.J. (1994) Clustal W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 22, 4673 4680.
    • (1994) Nucleic Acids Res , vol.22 , pp. 4673-4680
    • Thompson, J.D.1    Higgins, D.G.2    Gibson, T.J.3
  • 34
    • 0037164182 scopus 로고    scopus 로고
    • Enzymatic synthesis of optically active 2-methyl- and 2,2-dimethylcyclopropanecarboxylic acids and their derivatives
    • Wang, M.X. Feng, G.Q. (2002) Enzymatic synthesis of optically active 2-methyl- and 2,2-dimethylcyclopropanecarboxylic acids and their derivatives. J Mol Catal B: Enzym 18, 267 272.
    • (2002) J Mol Catal B: Enzym , vol.18 , pp. 267-272
    • Wang, M.X.1    Feng, G.Q.2
  • 37
    • 85153308784 scopus 로고    scopus 로고
    • The synthesis of chiral lactones from racemic gamma-hydroxyamides using the amidase from Brevibacterium sp strain R312
    • Yamaoka, J.S., Pridgeon, M.G., Miner, K.D., Taylor, S.K., Liao, M.K. Goyne, T.E. (2005) The synthesis of chiral lactones from racemic gamma-hydroxyamides using the amidase from Brevibacterium sp strain R312. FASEB J 19, A303.
    • (2005) FASEB J , vol.19
    • Yamaoka, J.S.1    Pridgeon, M.G.2    Miner, K.D.3    Taylor, S.K.4    Liao, M.K.5    Goyne, T.E.6
  • 38
    • 33846598795 scopus 로고    scopus 로고
    • A screening system for active and enantioselective amidase based on its acyl transfer activity
    • Zheng, R.C., Zheng, Y.G. Shen, Y.C. (2007a) A screening system for active and enantioselective amidase based on its acyl transfer activity. Appl Microbiol Biotechnol 74, 256 262.
    • (2007) Appl Microbiol Biotechnol , vol.74 , pp. 256-262
    • Zheng, R.C.1    Zheng, Y.G.2    Shen, Y.C.3
  • 39
    • 33947711988 scopus 로고    scopus 로고
    • Isolation and characterization of Delftia tsuruhatensis ZJB-05174, capable of R-enantioselective degradation of 2,2-dimethylcyclopropanecarboxamide
    • Zheng, R.C., Wang, Y.S., Liu, Z.Q., Xing, L.Y., Zheng, Y.G. Shen, Y.C. (2007b) Isolation and characterization of Delftia tsuruhatensis ZJB-05174, capable of R-enantioselective degradation of 2,2- dimethylcyclopropanecarboxamide. Res Microbiol 158, 258 264.
    • (2007) Res Microbiol , vol.158 , pp. 258-264
    • Zheng, R.C.1    Wang, Y.S.2    Liu, Z.Q.3    Xing, L.Y.4    Zheng, Y.G.5    Shen, Y.C.6
  • 40
    • 37249026821 scopus 로고    scopus 로고
    • Isolation, identification and characterization of Bacillus subtilis ZJB-063, a versatile nitrile-converting bacterium
    • Zheng, Y.G., Chen, J., Liu, Z.Q., Wu, M.H., Xing, L.Y. Shen, Y.C. (2008) Isolation, identification and characterization of Bacillus subtilis ZJB-063, a versatile nitrile-converting bacterium. Appl Microbiol Biotechnol 77, 985 993.
    • (2008) Appl Microbiol Biotechnol , vol.77 , pp. 985-993
    • Zheng, Y.G.1    Chen, J.2    Liu, Z.Q.3    Wu, M.H.4    Xing, L.Y.5    Shen, Y.C.6


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