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Volumn 52, Issue 26, 2004, Pages 8155-8162

Hydrolysis of nitriles using an immobilized nitrilase: Applications to the synthesis of methionine hydroxy analogue derivatives

Author keywords

Biotransformation; Dinitriles; Enzymes; Hydrolases; Methionine hydroxy analogue derivatives

Indexed keywords

ACID; BENZALKONIUM CHLORIDE; CARBOXYLIC ACID; CYANOHYDRIN; ENZYME; HYDROLASE; MANDELIC ACID; MANDELONITRILE; METHIONINE; METHIONINE DERIVATIVE; NITRILASE; NITRILE; PERTUZUMAB; UNCLASSIFIED DRUG;

EID: 11244298760     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf048827q     Document Type: Article
Times cited : (33)

References (49)
  • 2
    • 0003479152 scopus 로고
    • Springer-Verlag: New York
    • Davies, H. G.; Green, R. H.; Kelly, D. R.; and Roberts, S. M. Biotransformation in preparative Organic Chemistry; Academic Press, London, 1989. Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: New York, 1992.
    • (1992) Biotransformations in Organic Chemistry
    • Faber, K.1
  • 3
    • 4243794106 scopus 로고
    • The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks
    • Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks. Chem. Rev. 1992, 92(5), 1071-140.
    • (1992) Chem. Rev. , vol.92 , Issue.5 , pp. 1071-1140
    • Santaniello, E.1    Ferraboschi, P.2    Grisenti, P.3    Manzocchi, A.4
  • 4
    • 0642367795 scopus 로고
    • Asymmetric transformations catalyzed by enzymes in organic solvents
    • Klibanov, A. M. Asymmetric transformations catalyzed by enzymes in organic solvents. Acc. Chem. Res. 1990, 23(4), 114-20.
    • (1990) Acc. Chem. Res. , vol.23 , Issue.4 , pp. 114-120
    • Klibanov, A.M.1
  • 5
    • 0004088819 scopus 로고
    • Wiley-Interscience: New York
    • The Chemistry of the Cyano Group; Wiley-Interscience: New York, 1970; pp 77-86.
    • (1970) The Chemistry of the Cyano Group , pp. 77-86
  • 7
    • 33947348969 scopus 로고
    • Modification of the Sandmeyer synthesis of nitriles
    • Clarke, H. T.; Read, R. R. Modification of the Sandmeyer synthesis of nitriles. J. Am. Chem. Soc. 1924, 46, 1001.
    • (1924) J. Am. Chem. Soc. , vol.46 , pp. 1001
    • Clarke, H.T.1    Read, R.R.2
  • 9
    • 33847090362 scopus 로고
    • Chemistry of sulfonylmethyl isocyanides. 13. A general one-step synthesis of nitriles from ketones using tosylmethyl isocyanide. Introduction of a one-carbon unit
    • Oldeniel, O. H.; van Leusen, D.; van Leusen, A. M. Chemistry of sulfonylmethyl isocyanides. 13. A general one-step synthesis of nitriles from ketones using tosylmethyl isocyanide. Introduction of a one-carbon unit. J. Org. Chem. 1977, 42, 3114-8.
    • (1977) J. Org. Chem. , vol.42 , pp. 3114-3118
    • Oldeniel, O.H.1    Van Leusen, D.2    Van Leusen, A.M.3
  • 10
    • 85023062544 scopus 로고
    • Conversion of carboxamides and oximes to nitriles or imidoyl chlorides using a polymer-supported phosphine and carbon tetrachloride
    • Harrisson, C. R.; Hodge, P.; Rogers, W. J. Conversion of carboxamides and oximes to nitriles or imidoyl chlorides using a polymer-supported phosphine and carbon tetrachloride. Synthesis 1977, 41-3.
    • (1977) Synthesis , pp. 41-43
    • Harrisson, C.R.1    Hodge, P.2    Rogers, W.J.3
  • 11
    • 0001203673 scopus 로고
    • Homogeneously catalyzed hydration of nitriles to carboxamides
    • Bennett, M. A.; Yoshida, T. Homogeneously catalyzed hydration of nitriles to carboxamides. J. Am. Chem. Soc. 1973, 95, 3030-1.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 3030-3031
    • Bennett, M.A.1    Yoshida, T.2
  • 12
    • 85033823915 scopus 로고
    • Synthesis of carbamide by partial hydrolysis of the palladium chloride-nitrile complex
    • Paraskewas, S. Synthesis of carbamide by partial hydrolysis of the palladium chloride-nitrile complex. Synthesis 1974, 574-5.
    • (1974) Synthesis , pp. 574-575
    • Paraskewas, S.1
  • 13
    • 0344447702 scopus 로고
    • Catalytic hydrolysis of acrylonitrile to acrylamide under mild conditions
    • Chin, J.; Kim, J. H. Catalytic hydrolysis of acrylonitrile to acrylamide under mild conditions. Angew. Chem. 1990, 102(5), 580-2.
    • (1990) Angew. Chem. , vol.102 , Issue.5 , pp. 580-582
    • Chin, J.1    Kim, J.H.2
  • 14
    • 11244255618 scopus 로고
    • Supported ketonic compounds as catalysts for the dehydration of α-aminonitriles
    • Taillades, J.; Sola, R.; Brugidou, J.; Previero, A.; Commeyras, A. Supported ketonic compounds as catalysts for the dehydration of α-aminonitriles. Tetrahedron Lett. 1983, 24, 1501-4.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 1501-1504
    • Taillades, J.1    Sola, R.2    Brugidou, J.3    Previero, A.4    Commeyras, A.5
  • 15
    • 0038306772 scopus 로고
    • Strecker and related systems. X, Decomposition, and hydration of secondary α-aminonitriles in aqueous basic media. Autocatalytic hydration process and catalysis by acetone
    • Taillades, J.; Pascal, R.; Commeyras, A. Strecker and related systems. X, Decomposition, and hydration of secondary α-aminonitriles in aqueous basic media. Autocatalytic hydration process and catalysis by acetone. Tetrahedron 1978, 34, 2275-81.
    • (1978) Tetrahedron , vol.34 , pp. 2275-2281
    • Taillades, J.1    Pascal, R.2    Commeyras, A.3
  • 16
    • 85039480668 scopus 로고    scopus 로고
    • Process for the catalytic hydration of a cyanohydrin. Fr. Patent 2 631 338, 1988
    • Jammot, J.; Pascal, R.; Commeyras, A. Process for the catalytic hydration of a cyanohydrin. Fr. Patent 2 631 338, 1988.
    • Jammot, J.1    Pascal, R.2    Commeyras, A.3
  • 19
    • 0002162841 scopus 로고
    • Abramowicz, D. A., Ed.; Van Nostrand Reinhold: New York
    • Nagasawa, T.; Yamada, H. In Biocatalysis; Abramowicz, D. A., Ed.; Van Nostrand Reinhold: New York, 1990; p 277.
    • (1990) Biocatalysis , pp. 277
    • Nagasawa, T.1    Yamada, H.2
  • 20
    • 0024683215 scopus 로고
    • Microbial transformations of nitriles
    • Nagasawa, T.; Yamada, H. Microbial transformations of nitriles. Trends Biotechnol. 1989, 7(6), 153-8.
    • (1989) Trends Biotechnol. , vol.7 , Issue.6 , pp. 153-158
    • Nagasawa, T.1    Yamada, H.2
  • 21
    • 0001349004 scopus 로고
    • Monohydrolysis of an aliphatic dinitrile compound by nitrilase from Rhodococcus rhodochrous K22
    • Kobayashi, M.; Yanaka, N.; Nagasawa, T.; Yamada, H. Monohydrolysis of an aliphatic dinitrile compound by nitrilase from Rhodococcus rhodochrous K22. Tetrahedron 1990, 46, 5587-90.
    • (1990) Tetrahedron , vol.46 , pp. 5587-5590
    • Kobayashi, M.1    Yanaka, N.2    Nagasawa, T.3    Yamada, H.4
  • 22
    • 0024414263 scopus 로고
    • Selective hydrolysis of dinitriles into cyano-carboxylic acids by Rhodococcus rhodochrous N.C.I.B. 11216
    • Bengis-Garber, C.; Gutman, A. L. Selective hydrolysis of dinitriles into cyano-carboxylic acids by Rhodococcus rhodochrous N.C.I.B. 11216. Appl. Microbiol. Biotechnol. 1989, 32, 11-6.
    • (1989) Appl. Microbiol. Biotechnol. , vol.32 , pp. 11-16
    • Bengis-Garber, C.1    Gutman, A.L.2
  • 23
    • 0026021192 scopus 로고
    • Microbial hydrolysis as a potent method for the preparation of optically active nitriles, amides, and carboxylic acids
    • Kakeya, M.; Sakai, N.; Sugai, T.; Ohta, H. Microbial hydrolysis as a potent method for the preparation of optically active nitriles, amides, and carboxylic acids. Tetrahedron Lett. 1991, 32, 1343-6.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 1343-1346
    • Kakeya, M.1    Sakai, N.2    Sugai, T.3    Ohta, H.4
  • 24
    • 0642350821 scopus 로고
    • Production of stereospecific α-amino acids by biological hydrolysis of racemic α-amino nitriles
    • Arnaud, A.; Galzy, P.; Jallageas, J. C. Production of stereospecific α-amino acids by biological hydrolysis of racemic α-amino nitriles. Bull. Soc. Chim. Fr. 1980, 87-90.
    • (1980) Bull. Soc. Chim. Fr. , pp. 87-90
    • Arnaud, A.1    Galzy, P.2    Jallageas, J.C.3
  • 26
    • 0022457231 scopus 로고
    • Utilization of aliphatic amides and nitriles by Nocardia rhodochrous LL100-21
    • Linton, E. A.; Knowles, C. J. Utilization of aliphatic amides and nitriles by Nocardia rhodochrous LL100-21. J. Gen. Microbiol. 1986, 132, 1493-501.
    • (1986) J. Gen. Microbiol. , vol.132 , pp. 1493-1501
    • Linton, E.A.1    Knowles, C.J.2
  • 27
    • 0019092293 scopus 로고
    • Bioconversions of nitriles and their applications
    • Jallageas, J. C.; Arnaud, A.; Galzy, P. Bioconversions of nitriles and their applications. Adv. Biochem. Eng. 1980, 14, 1-32.
    • (1980) Adv. Biochem. Eng. , vol.14 , pp. 1-32
    • Jallageas, J.C.1    Arnaud, A.2    Galzy, P.3
  • 28
    • 0001328722 scopus 로고
    • Microbial degradation of nitrile compounds. Part V. Aliphatic nitrile hydratase from Arthrobacter sp. J-1. Purification and characterization
    • Asano, Y.; Fujishiro, K.; Tani, Y.; Yamada, H.; Microbial degradation of nitrile compounds. Part V. Aliphatic nitrile hydratase from Arthrobacter sp. J-1. Purification and characterization. Agric. Biol. Chem. 1982, 46, 1165-74.
    • (1982) Agric. Biol. Chem. , vol.46 , pp. 1165-1174
    • Asano, Y.1    Fujishiro, K.2    Tani, Y.3    Yamada, H.4
  • 29
    • 0025362833 scopus 로고
    • Isolation and characterization of a nitrile hydratase from a Rhodococcus sp
    • Hjort, C. M.; Godtfrendsen, S. E.; Emborg, C.; Isolation and characterization of a nitrile hydratase from a Rhodococcus sp. J. Chem. Technol. Biotechnol. 1990, 48(2), 2617-48.
    • (1990) J. Chem. Technol. Biotechnol. , vol.48 , Issue.2 , pp. 2617-2648
    • Hjort, C.M.1    Godtfrendsen, S.E.2    Emborg, C.3
  • 30
    • 0000677188 scopus 로고
    • Photoactivation of nitrile hydratase in Corynebacterium sp. N-774
    • Nakajima, Y.; Doi, T.; Satoh, Y.; Fujiwara, A.; Watanabe, I. Photoactivation of nitrile hydratase in Corynebacterium sp. N-774. Chem. Lett. 1987, 9, 1767-70.
    • (1987) Chem. Lett. , vol.9 , pp. 1767-1770
    • Nakajima, Y.1    Doi, T.2    Satoh, Y.3    Fujiwara, A.4    Watanabe, I.5
  • 31
    • 0023059799 scopus 로고
    • Nitrile hydratase of Brevibacterium R312-purification and characterization
    • Nagasawa, T.; Nanba, H.; Yamada, H. Nitrile hydratase of Brevibacterium R312-purification and characterization. Biochem. Biophys. Res. Commun. 1986, 139(3), 1305-12.
    • (1986) Biochem. Biophys. Res. Commun. , vol.139 , Issue.3 , pp. 1305-1312
    • Nagasawa, T.1    Nanba, H.2    Yamada, H.3
  • 32
    • 0023118310 scopus 로고
    • Nitrile hydratase of Pseudomonas chlororaphis B23. Purification and characterization
    • Nagasawa, T.; Nanba, H.; Ryuno, K.; Takenchi, K.; Yamada, H. Nitrile hydratase of Pseudomonas chlororaphis B23. Purification and characterization. Eur. J. Biochem. 1987, 162(3), 691-8.
    • (1987) Eur. J. Biochem. , vol.162 , Issue.3 , pp. 691-698
    • Nagasawa, T.1    Nanba, H.2    Ryuno, K.3    Takenchi, K.4    Yamada, H.5
  • 33
    • 0023229582 scopus 로고
    • Nitrile hydratase. The first non-heme iron enzyme with a typical low-spin iron(III)-active center
    • Sugiura, Y.; Kuwahara, J.; Nagasawa, T.; Yamada, H. Nitrile hydratase. The first non-heme iron enzyme with a typical low-spin iron(III)-active center. J. Am. Chem. Soc. 1987, 109(19), 5848-50.
    • (1987) J. Am. Chem. Soc. , vol.109 , Issue.19 , pp. 5848-5850
    • Sugiura, Y.1    Kuwahara, J.2    Nagasawa, T.3    Yamada, H.4
  • 34
    • 0001713876 scopus 로고
    • Ricinine nitrilase. I. Reaction product and substrate specificity
    • Hook, R. H.; Robinson, W. G. Ricinine nitrilase. I. Reaction product and substrate specificity. J. Biol. Chem. 1964, 239(12), 4257-62.
    • (1964) J. Biol. Chem. , vol.239 , Issue.12 , pp. 4257-4262
    • Hook, R.H.1    Robinson, W.G.2
  • 35
    • 0026632716 scopus 로고
    • Purification and characterization of the nitrilase from Alcaligenes faecalis ATCC 8750 responsible for enantioselective hydrolysis of mandelonitrile
    • Yamamoto, K.; Fujimatsu, I.; and Komatsu, K. Purification and characterization of the nitrilase from Alcaligenes faecalis ATCC 8750 responsible for enantioselective hydrolysis of mandelonitrile. J. Ferm. Bioeng. 1992, 73(6), 425-30.
    • (1992) J. Ferm. Bioeng. , vol.73 , Issue.6 , pp. 425-430
    • Yamamoto, K.1    Fujimatsu, I.2    Komatsu, K.3
  • 36
    • 0025953031 scopus 로고
    • Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750
    • Yamamoto, K.; Fukimatsu, I.; Oishi, K., Komatsu, K.; Production of R-(-)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750. Appl. Environ. Microbiol. 1991, 57(10), 3028-38.
    • (1991) Appl. Environ. Microbiol. , vol.57 , Issue.10 , pp. 3028-3038
    • Yamamoto, K.1    Fukimatsu, I.2    Oishi, K.3    Komatsu, K.4
  • 37
    • 85039475843 scopus 로고    scopus 로고
    • Aventis Animal Nutrition, U.S. Patent 6 180 359
    • Aventis Animal Nutrition, U.S. Patent 6 180 359.
  • 38
    • 0345667006 scopus 로고    scopus 로고
    • Supplemental animal marine preotein blend and rumen protected methionine hydroxy analogue for lactating dairy cows
    • Pas. Bernard, J. K. Supplemental animal marine preotein blend and rumen protected methionine hydroxy analogue for lactating dairy cows. Prof. Anim. Sci. 1997, 13, 149-54.
    • (1997) Prof. Anim. Sci. , vol.13 , pp. 149-154
    • Pas. Bernard, J.K.1
  • 39
    • 0023953972 scopus 로고
    • Degradation of methionine hydroxy analogue in the rumen of lactating cows
    • Prange, R. W.; Satter, L. D.; Jones, D. A. Degradation of methionine hydroxy analogue in the rumen of lactating cows. J. Dairy. Sci. 1988, 71, 525-9.
    • (1988) J. Dairy. Sci. , vol.71 , pp. 525-529
    • Prange, R.W.1    Satter, L.D.2    Jones, D.A.3
  • 40
    • 85039471226 scopus 로고    scopus 로고
    • Aventis Animal Nutrition, U.S. Patent 6 372 788
    • Aventis Animal Nutrition, U.S. Patent 6 372 788.
  • 41
    • 85039476601 scopus 로고    scopus 로고
    • European Patent No 0 628 257 A1, 1994
    • Moncoulon, R.; European Patent No 0 628 257 A1, 1994.
    • Moncoulon, R.1
  • 42
    • 0037462037 scopus 로고    scopus 로고
    • Enzymatic synthesis and characterisation of L-methionine and 2-hydroxy-4-methylthiobutanoic acid co-oligomers
    • Rajesh, M.; Kapela, S.; Nam, P.; Forciniti, D.; Lorbert, S.; Schasteen, C.; Enzymatic synthesis and characterisation of L-methionine and 2-hydroxy-4-methylthiobutanoic acid co-oligomers. J. Agric. Food. Chem. 2003, 51, 2461-7.
    • (2003) J. Agric. Food. Chem. , vol.51 , pp. 2461-2467
    • Rajesh, M.1    Kapela, S.2    Nam, P.3    Forciniti, D.4    Lorbert, S.5    Schasteen, C.6
  • 43
    • 85039476178 scopus 로고    scopus 로고
    • Monsanto, U.S. Patent 2 938 053, 1960
    • Monsanto, U.S. Patent 2 938 053, 1960.


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