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Volumn 20, Issue 5, 1997, Pages 333-339

Lipase-catalyzed hydrolysis of (4-phenoxyphenoxy)propyl acetates for preparation of enantiomerically pure juvenile hormone analogues

Author keywords

Enantiomerically pure secondary alcohol; Enantioselective hydrolysis; Juvenile hormone analogue; Lipase; Primary alcohol; Pseudomonas cepacia

Indexed keywords

BIOCONVERSION; ENZYMES; HYDROLYSIS; REACTION KINETICS; SUBSTRATES;

EID: 0031127866     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(96)00149-4     Document Type: Article
Times cited : (5)

References (34)
  • 3
    • 0039600026 scopus 로고
    • Juvenile hormone active compounds: Recent researches
    • Hatakoshi, M. and Nakayama, I. Juvenile hormone active compounds: Recent researches. Shokubutsu Boueki (in Japanese) 1987, 41, 339-347
    • (1987) Shokubutsu Boueki (In Japanese) , vol.41 , pp. 339-347
    • Hatakoshi, M.1    Nakayama, I.2
  • 4
    • 0142068645 scopus 로고
    • Effects of the juvenile hormone mimic S-31183 and trifluron on development of tea scale (Homoptera; Diaspidida)
    • Cooper, R. M. and Oetting, R. D. Effects of the juvenile hormone mimic S-31183 and trifluron on development of tea scale (Homoptera; Diaspidida). J. Entomol. Sci. 1985, 20, 429-434
    • (1985) J. Entomol. Sci. , vol.20 , pp. 429-434
    • Cooper, R.M.1    Oetting, R.D.2
  • 5
    • 0008337064 scopus 로고
    • Laboratory and field evaluation of an insect growth regulator, 4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether, as a mosquito larvicide
    • Kawada, H., Dohara, K., and Shinjo, G. Laboratory and field evaluation of an insect growth regulator, 4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether, as a mosquito larvicide. Jpn. J. Sanit. Zool. 1988, 39, 339-346
    • (1988) Jpn. J. Sanit. Zool. , vol.39 , pp. 339-346
    • Kawada, H.1    Dohara, K.2    Shinjo, G.3
  • 6
    • 85009643026 scopus 로고
    • Effects of the juvenile hormone analog pyriproxyfen, on Myzus persicae and Unaspis yanonensis
    • Hatakoshi, M., Shono, Y., Yamamoto, H., and Hirano, M. Effects of the juvenile hormone analog pyriproxyfen, on Myzus persicae and Unaspis yanonensis. Appl. Entomol. Zool. 1991, 26, 412-414
    • (1991) Appl. Entomol. Zool. , vol.26 , pp. 412-414
    • Hatakoshi, M.1    Shono, Y.2    Yamamoto, H.3    Hirano, M.4
  • 7
    • 84918175079 scopus 로고
    • The preparation of optical isomers of a new pyridyl ether compound having juvenile hormone activity and the comparison of juvenile hormone activities
    • Nishida, S., Hatakoshi, M., Nishizawa, K., Kisida, H., and Matsuo, N. The preparation of optical isomers of a new pyridyl ether compound having juvenile hormone activity and the comparison of juvenile hormone activities. Proc. Nihon-nogeikagakukai (in Japanese) 1985, 59, 540
    • (1985) Proc. Nihon-nogeikagakukai (In Japanese) , vol.59 , pp. 540
    • Nishida, S.1    Hatakoshi, M.2    Nishizawa, K.3    Kisida, H.4    Matsuo, N.5
  • 8
    • 0342908514 scopus 로고
    • Comparison of three-dimensional structures of compounds with juvenile hormone activity: A new pyridyl ether and terpenoid compounds
    • Iitaka. Y. and Itai, A., Eds. Tokyo
    • Motoki, T. and Takayama, C. Comparison of three-dimensional structures of compounds with juvenile hormone activity: A new pyridyl ether and terpenoid compounds. Abstr. Symp. Three-dimensional Struct. Drug Action (Iitaka. Y. and Itai, A., Eds.) Tokyo, 1985, 258-259
    • (1985) Abstr. Symp. Three-dimensional Struct. Drug Action , pp. 258-259
    • Motoki, T.1    Takayama, C.2
  • 10
    • 0003479152 scopus 로고
    • Springer-Verlag, Berlin, recent reviews
    • Davies, H. G., Green, R. H., Kelly, D. R., and Roberts, S. M. Biotransformations in Preparative Organic Chemistry. Academic Press, London, 1989; Faber, K. Biotransformations in Organic Chemistry. Springer-Verlag, Berlin, 1992, recent reviews
    • (1992) Biotransformations in Organic Chemistry
    • Faber, K.1
  • 11
    • 4243794106 scopus 로고
    • The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks
    • Santaniello, E., Ferraboschi, P., Grisenti, P., and Manzocchi, A. The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks. Chem. Rev. 1992, 92, 1071-1140
    • (1992) Chem. Rev. , vol.92 , pp. 1071-1140
    • Santaniello, E.1    Ferraboschi, P.2    Grisenti, P.3    Manzocchi, A.4
  • 12
    • 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, 114-120
    • (1990) Acc. Chem. Res. , vol.23 , pp. 114-120
    • Klibanov, A.M.1
  • 13
    • 0011052533 scopus 로고
    • Enzymatic preparation of optically active alcohols related to synthetic pyrethroids insecticides
    • Tramper, J., van der Plus, H. C., and Linko, P., Eds.. Elsevier, Amsterdam
    • Hirohara, H., Mitsuda, S., Ando, E., and Komaki, R. Enzymatic preparation of optically active alcohols related to synthetic pyrethroids insecticides. In: Biocatalysts in Organic Syntheses (Tramper, J., van der Plus, H. C., and Linko, P., Eds.). Elsevier, Amsterdam, 1985, 119-134
    • (1985) Biocatalysts in Organic Syntheses , pp. 119-134
    • Hirohara, H.1    Mitsuda, S.2    Ando, E.3    Komaki, R.4
  • 14
    • 0000939134 scopus 로고
    • Preparation of an optically pure secondary alcohol of pyrethroids using microbial lipases
    • Mitsuda, S., Umemura, T. and Hirohara, H. Preparation of an optically pure secondary alcohol of pyrethroids using microbial lipases. Appl. Microbiol. Biotechnol. 1988, 29, 310-315
    • (1988) Appl. Microbiol. Biotechnol. , vol.29 , pp. 310-315
    • Mitsuda, S.1    Umemura, T.2    Hirohara, H.3
  • 16
    • 0024864361 scopus 로고
    • Preparation of optically active pyrethroids via enzymatic resolution
    • Whitaker, J. R. and Sonnet, P. E., Eds.. American Chemical Society, Washington, DC
    • Umemura, T. and Hirohara, H. Preparation of optically active pyrethroids via enzymatic resolution. In: Biocatalysis in Agricultural Biotechnology. ACS Symp. Ser. 389 (Whitaker, J. R. and Sonnet, P. E., Eds.). American Chemical Society, Washington, DC, 1989, 371-384
    • (1989) Biocatalysis in Agricultural Biotechnology. ACS Symp. Ser. 389 , pp. 371-384
    • Umemura, T.1    Hirohara, H.2
  • 17
    • 0343343689 scopus 로고
    • Preparation of optically active pyrethroids using enzymatic reactions
    • (Oishi, T. and Akita, H., Eds.). I.P.C., Tokyo
    • Hirohara, H. Preparation of optically active pyrethroids using enzymatic reactions. In: Application of Biotechnology to Fine Chemicals (in Japanese). (Oishi, T. and Akita, H., Eds.). I.P.C., Tokyo, 1989, 183-211
    • (1989) Application of Biotechnology to Fine Chemicals (In Japanese) , pp. 183-211
    • Hirohara, H.1
  • 18
    • 0001562738 scopus 로고
    • Enantioselective hydrolysis of α-cyano-3-phenoxybenzyl acetate with Arthrobacter lipase
    • Mitsuda, S., Yamamoto, H., Umemura, T., Hirohara, H., and Nabeshima, S. Enantioselective hydrolysis of α-cyano-3-phenoxybenzyl acetate with Arthrobacter lipase. Agric. Biol. Chem. 1990, 54, 2907-2912
    • (1990) Agric. Biol. Chem. , vol.54 , pp. 2907-2912
    • Mitsuda, S.1    Yamamoto, H.2    Umemura, T.3    Hirohara, H.4    Nabeshima, S.5
  • 19
    • 84987210306 scopus 로고
    • Enzymatic optical resolution of a synthetic pyrethroid alcohol: Enantioselective transesterification by lipase in organic solvent
    • Mitsuda, S. and Nabeshima, S. Enzymatic optical resolution of a synthetic pyrethroid alcohol: Enantioselective transesterification by lipase in organic solvent. Rccl. Trav. Chim. Pays-Bas, 1991, 110, 151-154
    • (1991) Rccl. Trav. Chim. Pays-Bas , vol.110 , pp. 151-154
    • Mitsuda, S.1    Nabeshima, S.2
  • 20
    • 33751499686 scopus 로고
    • A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa
    • Kazlauskas, R. J., Weissflock, A. N. E., Rappaport, A. T., and Cuccia, L. A. A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa. J. Org. Chem. 1991, 56, 2656-2665
    • (1991) J. Org. Chem. , vol.56 , pp. 2656-2665
    • Kazlauskas, R.J.1    Weissflock, A.N.E.2    Rappaport, A.T.3    Cuccia, L.A.4
  • 24
    • 0001307149 scopus 로고
    • High-performance liquid chromatographic separation of chiral alcohols on chiral stationary phases
    • Oi, N. and Kitahara, H. High-performance liquid chromatographic separation of chiral alcohols on chiral stationary phases. J. Chromatogr. 1983, 265, 117-120
    • (1983) J. Chromatogr. , vol.265 , pp. 117-120
    • Oi, N.1    Kitahara, H.2
  • 25
    • 20644469267 scopus 로고
    • Quantitative analyses of biochemical kinetic resolutions of enantiomers
    • Chen, C.-S., Fujimoto, Y., Girdaukas, G., and Sih, C. J. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 1982, 104, 7294-7299
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 7294-7299
    • Chen, C.-S.1    Fujimoto, Y.2    Girdaukas, G.3    Sih, C.J.4
  • 26
    • 0001364513 scopus 로고
    • Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp
    • Burgess, K. and Jennings, L. D. Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp. J. Am. Chem. Soc. 1991, 113, 6129-6139
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6129-6139
    • Burgess, K.1    Jennings, L.D.2
  • 27
    • 0025732497 scopus 로고
    • Enantioselective synthesis of 6-cycloheptene-1,3,5-triol derivatives by enzymatic asymmetrization
    • Johnson, C. R., Golebiowski, A., Mcgill, T. K., and Steensma, D. H. Enantioselective synthesis of 6-cycloheptene-1,3,5-triol derivatives by enzymatic asymmetrization. Tetrahedron Lett. 1991, 32, 2597-2600
    • (1991) Tetrahedron Lett. , vol.32 , pp. 2597-2600
    • Johnson, C.R.1    Golebiowski, A.2    McGill, T.K.3    Steensma, D.H.4
  • 28
    • 33751390847 scopus 로고
    • Lipase-catalyzed enantioselective transesterification of O-trityl 1,2-diols. Practical synthesis of (R)-tritylglycidol
    • Kim, M.-J. and Choi, Y. K. Lipase-catalyzed enantioselective transesterification of O-trityl 1,2-diols. Practical synthesis of (R)-tritylglycidol. J. Org. Chem 1992, 57, 1605-1607
    • (1992) J. Org. Chem , vol.57 , pp. 1605-1607
    • Kim, M.-J.1    Choi, Y.K.2
  • 29
    • 0001095686 scopus 로고
    • Lipase YS-catalyzed enantioselective transesterification of alcohols of bicarbocyclic compounds
    • Naemura, K., Ida, H., and Fukuda, R. Lipase YS-catalyzed enantioselective transesterification of alcohols of bicarbocyclic compounds. Bull. Chem. Soc. Jpn. 1993, 66, 573-577
    • (1993) Bull. Chem. Soc. Jpn. , vol.66 , pp. 573-577
    • Naemura, K.1    Ida, H.2    Fukuda, R.3
  • 30
    • 0001484267 scopus 로고
    • Enantioselectivity of Candida rugosa lipase toward carboxylic acids: A predictive rule from substrate mapping and X-ray crystallography
    • Ahmed, S. H., Kazlauskas, R. J., Morinville, A. H., Grochulski, P., Schrag, J. D., and Cygler, M. Enantioselectivity of Candida rugosa lipase toward carboxylic acids: A predictive rule from substrate mapping and X-ray crystallography. Biocatalysis 1994, 9, 209-225
    • (1994) Biocatalysis , vol.9 , pp. 209-225
    • Ahmed, S.H.1    Kazlauskas, R.J.2    Morinville, A.H.3    Grochulski, P.4    Schrag, J.D.5    Cygler, M.6
  • 31
    • 0003572523 scopus 로고
    • Microbial resolution of 1-phenoxy-2-propanol by stereospecific decomposition and asymmetric hydrolysis of 1-phenoxy-2-propyl acetate
    • Yanase, H., Arishima, T., Kita, K., Nagai, J., Mizuno, Y., Takuma, Y., Endo, K., and Kato, N. Microbial resolution of 1-phenoxy-2-propanol by stereospecific decomposition and asymmetric hydrolysis of 1-phenoxy-2-propyl acetate. Biosci. Biotech. Biochem. 1993, 57, 1334-1337
    • (1993) Biosci. Biotech. Biochem. , vol.57 , pp. 1334-1337
    • Yanase, H.1    Arishima, T.2    Kita, K.3    Nagai, J.4    Mizuno, Y.5    Takuma, Y.6    Endo, K.7    Kato, N.8
  • 32
    • 37049070583 scopus 로고
    • Lipase YS-catalyzed acylation of alcohols: A predictive active site model for lipase YS to identify which enantiomer of a primary or a secondary alcohol reacts faster in this acylation
    • Naemura, K., Fukuda, R., Konishi, M., Hirose, K., and Tobe, Y. Lipase YS-catalyzed acylation of alcohols: A predictive active site model for lipase YS to identify which enantiomer of a primary or a secondary alcohol reacts faster in this acylation. J. Chem. Soc. Perkin Trans. 1, 1994, 1253-1256
    • (1994) J. Chem. Soc. Perkin Trans. 1 , pp. 1253-1256
    • Naemura, K.1    Fukuda, R.2    Konishi, M.3    Hirose, K.4    Tobe, Y.5
  • 33
    • 0025100296 scopus 로고
    • Active-site model for interpreting and predicting the specificity of pig liver esterase
    • Toone, E. J., Werth, M. J., and Jones, J. B. Active-site model for interpreting and predicting the specificity of pig liver esterase. J. Am. Chem. Soc. 1990, 112, 4946-4952
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4946-4952
    • Toone, E.J.1    Werth, M.J.2    Jones, J.B.3
  • 34
    • 0028075638 scopus 로고
    • Elucidating structure-mechanism relationships in lipases: Prospects for predicting and engineering catalytic properties
    • Kazlauskas, R. J. Elucidating structure-mechanism relationships in lipases: Prospects for predicting and engineering catalytic properties. Trends Biotechnol. 1994, 12, 464-472
    • (1994) Trends Biotechnol. , vol.12 , pp. 464-472
    • Kazlauskas, R.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.