메뉴 건너뛰기




Volumn 29, Issue 6, 2011, Pages 320-327

Kinetic resolution of 2-chloro-3,3,3-trifluoropropanoic acid esters catalyzed by lipase from Candida rugosa

Author keywords

C. rugosa lipase; CLEA; flourinated compounds; kinetic resolution; P. fluorescens esterase; transesterefication

Indexed keywords

CLEA; FLOURINATED COMPOUNDS; KINETIC RESOLUTION; P. FLUORESCENS ESTERASE; TRANSESTEREFICATION;

EID: 82355191985     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.3109/10242422.2011.634906     Document Type: Article
Times cited : (6)

References (32)
  • 1
    • 0001484267 scopus 로고
    • Enantioselectivity of Candida rugosa lipase toward carboxylic acids: A predictive rule from substrate mapping and X-ray crystallography
    • Ahmed SN, Kazlauskas RJ, Morinville AH, Grochulski P, Schrag JD, Cygler M. 1994. Enantioselectivity of Candida rugosa lipase toward carboxylic acids: a predictive rule from substrate mapping and X-ray crystallography. Biocatal Biotransformation 9:209-225.
    • (1994) Biocatal Biotransformation. , vol.9 , pp. 209-225
    • Ahmed, S.N.1    Kazlauskas, R.J.2    Morinville, A.H.3    Grochulski, P.4    Schrag, J.D.5    Cygler, M.6
  • 2
    • 79959421993 scopus 로고    scopus 로고
    • Organic fl uorine compounds: A great opportunity for enhanced materials properties
    • Berger R, Resnati G, Metrangolo P, Weber E, Hulliger J. 2011. Organic fl uorine compounds: a great opportunity for enhanced materials properties. Chem Soc Rev 40:3496-3508.
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 3496-3508
    • Berger, R.1    Resnati, G.2    Metrangolo, P.3    Weber, E.4    Hulliger, J.5
  • 4
    • 33744802202 scopus 로고    scopus 로고
    • Catalytic asymmetric fl uorinations
    • Bobbio C, Gouverneur V. 2006. Catalytic asymmetric fl uorinations. Org Biomol Chem 4:2065-2075.
    • (2006) Org. Biomol. Chem. , vol.4 , pp. 2065-2075
    • Bobbio, C.1    Gouverneur, V.2
  • 6
    • 0021671748 scopus 로고
    • Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: Asymmetric hydrolysis, esterification, and transesterification
    • DOI 10.1002/bit.260261209
    • Cambou B, Klibanov AM. 1984. Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: asymmetric hydrolysis, esterifi cation, and transesterifi cation. Biotechnol Bioeng 26:1449-1454. (Pubitemid 15164207)
    • (1984) Biotechnology and Bioengineering , vol.26 , Issue.12 , pp. 1449-1454
    • Cambou, B.1    Klibanov, A.M.2
  • 7
    • 33745749592 scopus 로고    scopus 로고
    • Stereoselective enzymatic acylations transesterifi cations
    • Chenevert R, Pelchat N, Jacques F. 2006. Stereoselective enzymatic acylations (transesterifi cations). Curr Org Chem 10:1067-1094.
    • (2006) Curr. Org. Chem. , vol.10 , pp. 1067-1094
    • Chenevert, R.1    Pelchat, N.2    Jacques, F.3
  • 8
    • 82355175907 scopus 로고    scopus 로고
    • Fluorine-containing chiral compounds of biomedical interest
    • Ramachandran PV editor Washington DC: American Chemical Society.
    • Filler R. 2000. Fluorine-containing chiral compounds of biomedical interest. In: Ramachandran PV, editor. Asymmetric Fluoroorganic Chemistry. Washington DC: American Chemical Society. p 1.
    • (2000) Asymmetric Fluoroorganic Chemistry , pp. 1
    • Filler, R.1
  • 9
    • 37049015378 scopus 로고    scopus 로고
    • Sol-gels and cross-linked aggregates of lipase PS from Burkholderia cepacia and their application in dry organic solvents
    • DOI 10.1016/j.molcatb.2007.09.004, PII S1381117707001749, Contriburions by COST Action D25: Applied Biocatalysis. Stereoselective and Environmentally Friendly Reactions Catalysed by Enzymes
    • Hara P, Hanefeld U, Kanerva LT. 2008. Sol-gels and cross-linked aggregates of lipase PS from Burkholderia cepacia and their application in dry organic solvents. J Mol Catal B: Enzym 50:80-86. (Pubitemid 350245630)
    • (2008) Journal of Molecular Catalysis B: Enzymatic , vol.50 , Issue.2-4 , pp. 80-86
    • Hara, P.1    Hanefeld, U.2    Kanerva, L.T.3
  • 10
    • 0344815505 scopus 로고
    • Fluorohalogeno compounds II sonochemical approach to 3 3 3-trifl uoropropionic acids
    • Hemer I, Havlicek J, Dedek V. 1986. Fluorohalogeno compounds. II. Sonochemical approach to 3,3,3-trifl uoropropionic acids. J Fluor Chem 34:241-250.
    • (1986) J. Fluor. Chem. , vol.34 , pp. 241-250
    • Hemer, I.1    Havlicek, J.2    Dedek, V.3
  • 11
    • 19544375431 scopus 로고    scopus 로고
    • Synthesis of PPAR agonist via asymmetric hydrogenation of a cinnamic acid derivative and stereospecific displacement of (S)-2-chloropropionic acid
    • DOI 10.1021/ol050367e
    • Houpis IN, Patterson LE, Alt CA, Rizzo JR, Zhang TY, Haurez M. 2005. Synthesis of PPAR agonist via asymmetric hydrogenation of a cinnamic acid derivative and stereospecifi c displacement of ( S )-2-chloropropionic acid. Org Lett 7:1947-1950. (Pubitemid 40732020)
    • (2005) Organic Letters , vol.7 , Issue.10 , pp. 1947-1950
    • Houpis, I.N.1    Patterson, L.E.2    Alt, C.A.3    Rizzo, J.R.4    Zhang, T.Y.5    Haurez, M.6
  • 12
    • 0032512020 scopus 로고    scopus 로고
    • Catalytic asymmetric synthesis of chiral fluoroorganic compounds
    • DOI 10.1016/S0040-4020(98)00740-6, PII S0040402098007406
    • Iseki K. 1998. Catalytic asymmetric synthesis of chiral fl uoroorganic compounds. Tetrahedron 54:13887-13914. (Pubitemid 28485004)
    • (1998) Tetrahedron , vol.54 , Issue.46 , pp. 13887-13914
    • Iseki, K.1
  • 13
    • 4544369746 scopus 로고    scopus 로고
    • The unique role of fluorine in the design of active ingredients for modern crop protection
    • DOI 10.1002/cbic.200300833
    • Jeschke P. 2004. The unique role of fl uorine in the design of active ingredients for modern crop protection. ChemBioChem 5:570-589. (Pubitemid 39257080)
    • (2004) ChemBioChem , vol.5 , Issue.5 , pp. 570-589
    • Jeschke, P.1
  • 14
    • 77649199638 scopus 로고    scopus 로고
    • Synthesis and biological activity of 4-4 6-disubstituted-pyrimidin-2- yloxyphenoxy acetates
    • Jiang L, Wang H, Wang M, Teng X. 2010. Synthesis and biological activity of 4-(4,6-disubstituted-pyrimidin-2-yloxy)phenoxy acetates. Molecules 15:1074-1081.
    • (2010) Molecules , vol.15 , pp. 1074-1081
    • Jiang, L.1    Wang, H.2    Wang, M.3    Teng, X.4
  • 16
    • 20644455034 scopus 로고
    • Resolution of racemic mixtures via lipase catalysis in organic solvents
    • Kirchner G, Scollar MP, Klibanov AM. 1985. Resolution of racemic mixtures via lipase catalysis in organic solvents. J Am Chem Soc 107:7072-7076.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 7072-7076
    • Kirchner, G.1    Scollar, M.P.2    Klibanov, A.M.3
  • 17
    • 0002405646 scopus 로고    scopus 로고
    • Enzymatically controlled reactions of organofl uorine compounds
    • Kitazume T, Yamazaki T. 1997. Enzymatically controlled reactions of organofl uorine compounds. Top Curr Chem 193:91-130.
    • (1997) Top. Curr. Chem. , vol.193 , pp. 91-130
    • Kitazume, T.1    Yamazaki, T.2
  • 18
    • 0032524178 scopus 로고    scopus 로고
    • Characterization and enantioselectivity of a recombinant esterase from Pseudomonas fluorescens
    • DOI 10.1016/S0141-0229(98)00004-0, PII S0141022998000040
    • Krebsfänger N. Zocher F. Altenbuchner J.Bornscheuer U.T. 1998 Characterization and enantioselectivity of a recombinant esterase from Pseudomonas fl uorescens . Enzyme Microb Technol 22: 641-646. (Pubitemid 28260581)
    • (1998) Enzyme and Microbial Technology , vol.22 , Issue.7 , pp. 641-646
    • Krebsfanger, N.1    Zocher, F.2    Altenbuchner, J.3    Bornscheuer, U.T.4
  • 19
    • 0025145516 scopus 로고
    • Short chain flavour esters synthesis by microbial lipases
    • DOI 10.1007/BF01030756
    • Langrand G, Rondot N, Triantaphylides C, Baratti J. 1990. Short chain fl avour esters synthesis by microbial lipases. Biotechnol Lett 12:581-586. (Pubitemid 20298428)
    • (1990) Biotechnology Letters , vol.12 , Issue.8 , pp. 581-586
    • Langrand, G.1    Rondot, N.2    Triantaphylides, C.3    Baratti, J.4
  • 20
    • 0035911359 scopus 로고    scopus 로고
    • Mapping the substrate selectivity of new hydrolases using colorimetric screening: Lipases from Bacillus thermocatenulatus and Ophiostoma piliferum, esterases from Pseudomonas fluorescens and Streptomyces diastatochromogenes
    • DOI 10.1016/S0957-4166(01)00072-6, PII S0957416601000726
    • Liu AMF, Somers NA, Kazlauskas RJ, Brush TS, Zocher F, Enzelberger MM, Bornscheuer UW, Horsman GP, Mezzetti A, Schmidt-Dannert C, Schmid RD. 2001. Mapping the substrate selectivity of new hydrolases using colorimetric screening: lipases from Bacillus thermocatenulatus and Ophiostoma piliferum , esterases from Pseudomonas fl uorescens and Streptomyces diastatochromogenes . Tetrahedron Asymmetry 12:545-556. (Pubitemid 32324014)
    • (2001) Tetrahedron Asymmetry , vol.12 , Issue.4 , pp. 545-556
    • Liu, A.M.F.1    Somers, N.A.2    Kazlauskas, R.J.3    Brush, T.S.4    Zocher, F.5    Enzelberger, M.M.6    Bornscheuer, U.T.7    Horsman, G.P.8    Mezzetti, A.9    Schmidt-Dannert, C.10    Schmid, R.D.11
  • 21
    • 0036671720 scopus 로고    scopus 로고
    • Cross-linked enzyme aggregates with enhanced activity: Application to lipases
    • DOI 10.1023/A:1019863314646
    • LÓpez-Serrano P.Cao L.Van Rantwijk F.Sheldon R.A. 2002 Cross-linked enzyme aggregates with enhanced activity: Application to lipases Biotechnol. Lett. 24 1379-1383 (Pubitemid 35000938)
    • (2002) Biotechnology Letters , vol.24 , Issue.16 , pp. 1379-1383
    • Lopez-Serrano, P.1    Cao, L.2    Van Rantwijk, F.3    Sheldon, R.A.4
  • 23
    • 0037413432 scopus 로고    scopus 로고
    • Enantioselectivity of Candida rugosa lipase in the hydrolysis of 2-chloropropionic acid methyl ester
    • DOI 10.1016/S1381-1177(02)00143-1, PII S1381117702001431
    • Overbeeke PLA, Jongejan JA. 2003. Enantioselectivity of Candida rugosa lipase in the hydrolysis of 2-chloropropionic acid methyl ester. J Mol Catal: B Enzym 21:89-91. (Pubitemid 35477594)
    • (2003) Journal of Molecular Catalysis B: Enzymatic , vol.21 , Issue.1-2 , pp. 89-91
    • Overbeeke, P.L.A.1    Jongejan, J.A.2
  • 24
    • 77954038128 scopus 로고    scopus 로고
    • Activity and enantioselectivity of the hydroxynitrile lyase mehnl in dry organic solvents
    • Paravidino M, Sorgedrager MJ, Orru RVA, Hanefeld U. 2010. Activity and Enantioselectivity of the Hydroxynitrile Lyase MeHNL in Dry Organic Solvents. Chem Eur J 16:7596-7604.
    • (2010) Chem. Eur. J. , vol.16 , pp. 7596-7604
    • Paravidino, M.1    Sorgedrager, M.J.2    Orru, R.V.A.3    Hanefeld, U.4
  • 25
    • 0043118219 scopus 로고
    • Notes - The addition of alkanols to 1 1 2-trichloro-3 3 3-trifl uoropropene - Some corrective data
    • Park JD, Sweeney WM, Lacher JR. 1956. Notes - the addition of alkanols to 1,1,2,-trichloro-3,3,3-trifl uoropropene - some corrective data. J Org Chem 21:1035-1036.
    • (1956) J. Org. Chem. , vol.21 , pp. 1035-1036
    • Park, J.D.1    Sweeney, W.M.2    Lacher, J.R.3
  • 29
    • 79251469073 scopus 로고    scopus 로고
    • Cross-linked enzyme aggregates as industrial biocatalysts
    • Sheldon RA. 2011. Cross-linked enzyme aggregates as industrial biocatalysts. Org Process Res Dev 15:213-223.
    • (2011) Org. Process. Res. Dev. , vol.15 , pp. 213-223
    • Sheldon, R.A.1
  • 30
    • 0031455616 scopus 로고    scopus 로고
    • The enantiomeric ratio: Origin, determination and prediction
    • DOI 10.1016/S0141-0229(97)00066-5, PII S0141022997000665
    • Straathof AJJ, Jongejan JA. 1997. The enantiomeric ratio: origin, determination and prediction. Enzyme Microb Technol 21:559-571. (Pubitemid 28005800)
    • (1997) Enzyme and Microbial Technology , vol.21 , Issue.8 , pp. 559-571
    • Straathof, A.J.J.1    Jongejan, J.A.2
  • 31
    • 0026635877 scopus 로고
    • Lipases from different sources vary widely in dependence of catalytic activity on water activity
    • Valivety RH, Halling PJ, Peilow AD, Macrae AR. 1992. Lipases from different sources vary widely in dependence of catalytic activity on water activity. Biochim Biophys Acta 1122: 143-146.
    • (1992) Biochim. Biophys. Acta. , vol.1122 , pp. 143-146
    • Valivety, R.H.1    Halling, P.J.2    Peilow, A.D.3    Macrae, A.R.4
  • 32
    • 13444309335 scopus 로고    scopus 로고
    • Candida Rugosa lipase-catalyzed kinetic resolution of hydroxy- arylpropionates and hydroxy-aryl-oxo-pentanoates
    • DOI 10.1016/j.tet.2004.12.059, PII S0040402005000086
    • Xu C, Yuan C. 2005. Candida Rugosa lipase-catalyzed kinetic resolution of β?-hydroxy- β?-arylpropionates and α-hydroxy- α?-aryl- β?-oxo-pentanoates. Tetrahed 61:2169-2186 (Pubitemid 40203212)
    • (2005) Tetrahedron , vol.61 , Issue.8 , pp. 2169-2186
    • Xu, C.1    Yuan, C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.