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Volumn 17, Issue 7, 2013, Pages 672-681

Lipase-catalyzed dynamic combinatorial resolution and the synthesis of heteroaromatic cyanohydrin ester enantiomers

Author keywords

Acylation; Base catalysis; Cyanohydrin; Dynamic combinatorial resolution; Dynamic kinetic resolution; Enzyme catalysis; Lipase catalysis

Indexed keywords

ACETONE; CATALYSIS; SODIUM CARBONATE; THIOPHENE;

EID: 84876730613     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272811317070003     Document Type: Article
Times cited : (9)

References (33)
  • 1
    • 0032820242 scopus 로고    scopus 로고
    • Dynamic combinatorial chemistry and virtual combinatorial libraries
    • Lehn, J.-M. Dynamic combinatorial chemistry and virtual combinatorial libraries. Chem. Eur. J., 1999, 5, 2455-2463.
    • (1999) Chem. Eur. J , vol.5 , pp. 2455-2463
    • Lehn, J.-M.1
  • 2
    • 33846699703 scopus 로고    scopus 로고
    • From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry
    • Lehn, J.-M. From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry. Chem. Soc. Rev., 2007, 36, 151-160.
    • (2007) Chem. Soc. Rev , vol.36 , pp. 151-160
    • Lehn, J.-M.1
  • 4
    • 15044347857 scopus 로고    scopus 로고
    • Receptor assisted combinatorial chemistry: Thermodynamics and kinetics in drug discovery
    • Cheeseman, J. D., Corbett, A. D., Gleason, J. L., Kazlauskas, R. J. Receptor assisted combinatorial chemistry: thermodynamics and kinetics in drug discovery. Chem. Eur. J., 2005, 11, 1708-1716.
    • (2005) Chem. Eur. J , vol.11 , pp. 1708-1716
    • Cheeseman, J.D.1    Corbett, A.D.2    Gleason, J.L.3    Kazlauskas, R.J.4
  • 5
    • 33846687723 scopus 로고    scopus 로고
    • Dynamic combinatorial resolution: Direct asymmetric lipase-mediated screening of a dynamic nitroaldol library
    • Vongvilai, P.; Angelin, M.; Larsson, R.; Ramström, O. Dynamic combinatorial resolution: direct asymmetric lipase-mediated screening of a dynamic nitroaldol library. Angew. Chem. Int. Ed., 2007, 46, 948-950.
    • (2007) Angew. Chem. Int. Ed , vol.46 , pp. 948-950
    • Vongvilai, P.1    Angelin, M.2    Larsson, R.3    Ramström, O.4
  • 6
    • 4544244707 scopus 로고    scopus 로고
    • Catalytic self-screening of cholinesterase substrates from a dynamic combinatorial thioester library
    • Larsson, R.; Pei, Z.; Ramström, O. Catalytic self-screening of cholinesterase substrates from a dynamic combinatorial thioester library. Angew. Chem. Int. Ed., 2004, 43, 3716-3718.
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 3716-3718
    • Larsson, R.1    Pei, Z.2    Ramström, O.3
  • 7
    • 33745819380 scopus 로고    scopus 로고
    • Dynamic combinatorial thioester libraries for efficient catalytic self-screening of hydrolase substrates
    • Larsson, R.; Ramström, O. Dynamic combinatorial thioester libraries for efficient catalytic self-screening of hydrolase substrates. Eur. J. Org. Chem., 2005, 285-291.
    • (2005) Eur. J. Org. Chem , pp. 285-291
    • Larsson, R.1    Ramström, O.2
  • 8
    • 70349914540 scopus 로고    scopus 로고
    • Dynamic asymmetric multicomponent resolution: Lipase-mediated amidation of a double dynamic covalent system
    • Vongvilai, P.; Ramström, O. Dynamic asymmetric multicomponent resolution: lipase-mediated amidation of a double dynamic covalent system. J. Am. Chem. Soc., 2009, 131, 14419-14425.
    • (2009) J. Am. Chem. Soc , vol.131 , pp. 14419-14425
    • Vongvilai, P.1    Ramström, O.2
  • 9
    • 43449087343 scopus 로고    scopus 로고
    • Crystallization-induced secondary selection from a tandem driven dynamic combinatorial resolution process
    • Angelin, M.; Fischer, A.; Ramström, O. Crystallization-induced secondary selection from a tandem driven dynamic combinatorial resolution process. J. Org. Chem., 2008, 73, 3593-3595.
    • (2008) J. Org. Chem , vol.73 , pp. 3593-3595
    • Angelin, M.1    Fischer, A.2    Ramström, O.3
  • 10
    • 60749104310 scopus 로고    scopus 로고
    • Lewis acid catalyzed asymmetric cyanohydrin synthesis
    • North, M.; Usanov, D. L.; Young, C. Lewis acid catalyzed asymmetric cyanohydrin synthesis. Chem. Rev., 2008, 108, 5146-5226.
    • (2008) Chem. Rev , vol.108 , pp. 5146-5226
    • North, M.1    Usanov, D.L.2    Young, C.3
  • 11
    • 77956018130 scopus 로고    scopus 로고
    • Recent procress in the chemically catalyzed enantioselective synthesis of cyanohydrins
    • Wang, W.; Liu, X.; Lin, L.; Feng, X. Recent procress in the chemically catalyzed enantioselective synthesis of cyanohydrins. Eur. J. Org. Chem., 2010, 4751-4769.
    • (2010) Eur. J. Org. Chem , pp. 4751-4769
    • Wang, W.1    Liu, X.2    Lin, L.3    Feng, X.4
  • 12
    • 65949118468 scopus 로고    scopus 로고
    • Enantioselective enzymecatalysed synthesis of cyanohydrins
    • Holt, J.; Hanefeld, U. Enantioselective enzymecatalysed synthesis of cyanohydrins. Curr. Org. Synth., 2009, 6, 15-37.
    • (2009) Curr. Org. Synth , vol.6 , pp. 15-37
    • Holt, J.1    Hanefeld, U.2
  • 14
    • 0000874098 scopus 로고
    • Lipase-catalyzed kinetic resolution with in situ racemization: One-pot synthesis of optically active cyanohydrin acetates from aldehydes
    • Inagaki, M.; Hiratake, J.; Nishioka, T.; Oda, J. Lipase-catalyzed kinetic resolution with in situ racemization: one-pot synthesis of optically active cyanohydrin acetates from aldehydes. J. Am. Chem. Soc., 1991, 113, 9360-9361.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 9360-9361
    • Inagaki, M.1    Hiratake, J.2    Nishioka, T.3    Oda, J.4
  • 15
    • 0001690116 scopus 로고
    • One-pot synthesis of optically active cyanohydrin acetates from aldehydes via lipase-catalyzed kinetic resolution coupled with in situ formation and racemization of cyanohydrins
    • Inagaki, M.; Hiratake, J., Nishioka, T.; Oda, J. One-pot synthesis of optically active cyanohydrin acetates from aldehydes via lipase-catalyzed kinetic resolution coupled with in situ formation and racemization of cyanohydrins. J. Org. Chem., 1992, 57, 5643-5649.
    • (1992) J. Org. Chem , vol.57 , pp. 5643-5649
    • Inagaki, M.1    Hiratake, J.2    Nishioka, T.3    Oda, J.4
  • 16
    • 79551703938 scopus 로고    scopus 로고
    • In situ evaluation of lipase performances through dynamic asymmetric cyanohydrin resolution
    • Sakulsombat, M.; Vongvilai, P.; Ramström, O. In situ evaluation of lipase performances through dynamic asymmetric cyanohydrin resolution. Org. Biomol. Chem., 2011, 9, 1112-1117.
    • (2011) Org. Biomol. Chem , vol.9 , pp. 1112-1117
    • Sakulsombat, M.1    Vongvilai, P.2    Ramström, O.3
  • 17
    • 0000384421 scopus 로고
    • Optically active cyanohydrins and enzyme catalysis
    • Kanerva, L. T.; Rahiala, K.; Sundholm, O. Optically active cyanohydrins and enzyme catalysis. Biocatalysis, 1994, 10, 169-180.
    • (1994) Biocatalysis , vol.10 , pp. 169-180
    • Kanerva, L.T.1    Rahiala, K.2    Sundholm, O.3
  • 18
    • 0037424372 scopus 로고    scopus 로고
    • Candida antarctica lipase A in the dynamic resolution of novel furylbenzotiazol-base cyanohydrin acetates
    • Paizs, C.; Toşa, M.; Majdik, C.; Tähtinen, P.; Irimie, F. D.; Kanerva, L. T. Candida antarctica lipase A in the dynamic resolution of novel furylbenzotiazol-base cyanohydrin acetates. Tetrahedron: Asymmetry, 2003, 14, 619-627.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 619-627
    • Paizs, C.1    Toşa, M.2    Majdik, C.3    Tähtinen, P.4    Irimie, F.D.5    Kanerva, L.T.6
  • 19
    • 0037805631 scopus 로고    scopus 로고
    • Preparation of novel phenylfuran-based cyanohydrin esters: Lipase-catalysed kinetic and dynamic resolution
    • Paizs, C.; Tähtinen, P.; Lundell, K.; Poppe, L.; Irimie, F. D.; Kanerva, L.T. Preparation of novel phenylfuran-based cyanohydrin esters: lipase-catalysed kinetic and dynamic resolution. Tetrahedron: Asymmetry, 2003, 14, 1895-1904.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 1895-1904
    • Paizs, C.1    Tähtinen, P.2    Lundell, K.3    Poppe, L.4    Irimie, F.D.5    Kanerva, L.T.6
  • 20
    • 4944251663 scopus 로고    scopus 로고
    • Biocatalytic enantioselective preparation of phenothiazine-based cyanohydrin acetates: Kinetic and dynamic kinetic resolution
    • Paizs, C.; Tähtinen, P.; Toşa, M.; Majdik, C.; Irimie, F. D.; Kanerva, L. T. Biocatalytic enantioselective preparation of phenothiazine-based cyanohydrin acetates: kinetic and dynamic kinetic resolution. Tetrahedron: Asymmetry, 2004, 60, 10533-10540.
    • (2004) Tetrahedron: Asymmetry , vol.60 , pp. 10533-10540
    • Paizs, C.1    Tähtinen, P.2    Toşa, M.3    Majdik, C.4    Irimie, F.D.5    Kanerva, L.T.6
  • 21
    • 78650137930 scopus 로고    scopus 로고
    • Applying biocatalysis to the synthesis of enantio- and diastereopure cyanohydrin mannosides
    • Hietanen, A.; Ekholm, F. S.; Leino, R. and Kanerva, L. T. Applying biocatalysis to the synthesis of enantio- and diastereopure cyanohydrin mannosides. Eur. J. Org. Chem., 2010, 6974-6980.
    • (2010) Eur. J. Org. Chem , pp. 6974-6980
    • Hietanen, A.1    Ekholm, F.S.2    Leino, R.3    Kanerva, L.T.4
  • 22
    • 84860610939 scopus 로고    scopus 로고
    • One-Pot Oxidation - Hydrocyanation Sequence Coupled to Lipase- Catalyzed Diastereoresolution in the Chemoenzymatic Synthesis of Sugar Cyanohydrin Esters
    • Hietanen, A.; Kanerva, L. T. One-Pot Oxidation - Hydrocyanation Sequence Coupled to Lipase- Catalyzed Diastereoresolution in the Chemoenzymatic Synthesis of Sugar Cyanohydrin Esters. Eur. J. Org. Chem., 2012, 2669-2860.
    • (2012) Eur. J. Org. Chem , pp. 2669-2860
    • Hietanen, A.1    Kanerva, L.T.2
  • 23
    • 0000604617 scopus 로고
    • Cyanohydrins - a general synthesis
    • Gassman, P. and Talley, J. J. Cyanohydrins - a general synthesis. Tetrahedron Lett., 1978, 3773-3776.
    • (1978) Tetrahedron Lett , pp. 3773-3776
    • Gassman, P.1    Talley, J.J.2
  • 24
    • 20644469267 scopus 로고
    • Quantitative Analyses of Biochemical Kinetic Resolutions of Enantiomers
    • Chen, C.-S.; Fujimoto, Y.; Girdaukas, G.; 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
  • 25
    • 0031455616 scopus 로고    scopus 로고
    • The enantiomeric ratio: Origin, determination and prediction
    • Straathof, A. J. J.; Jongejan, J. A. The enantiomeric ratio: origin, determination and prediction. Enzyme Microb. Technol., 1997, 21, 559-571.
    • (1997) Enzyme Microb. Technol , vol.21 , pp. 559-571
    • Straathof, A.J.J.1    Jongejan, J.A.2
  • 26
    • 0037007664 scopus 로고    scopus 로고
    • Enantioselective formation of mandelonitrile acetate - investigation of a dynamic kinetic resolution
    • Li, Y.-X; Straathof, A. J. J.; Hanefeld, U. Enantioselective formation of mandelonitrile acetate - investigation of a dynamic kinetic resolution. Tetrahedron: Asymmetry, 2002, 13, 739-743.
    • (2002) Tetrahedron: Asymmetry , vol.13 , pp. 739-743
    • Li, Y.-X.1    Straathof, A.J.J.2    Hanefeld, U.3
  • 30
    • 0030053212 scopus 로고    scopus 로고
    • Preparation of optically active cyanohydrins using the (S)-hydroxynitrile lyase from Hevea brasiliensis
    • Schmidt, M.; Hervé, S.; Klempier, N.; Griengl, H. Preparation of optically active cyanohydrins using the (S)-hydroxynitrile lyase from Hevea brasiliensis. Tetrahedron, 1996, 52, 7833-7840.
    • (1996) Tetrahedron , vol.52 , pp. 7833-7840
    • Schmidt, M.1    Hervé, S.2    Klempier, N.3    Griengl, H.4
  • 31
    • 0037437034 scopus 로고    scopus 로고
    • The chemistry of diaminomaleonitrile and its utility in heterocyclic synthesis
    • Al-Azmi, A.; Elassar, A.-Z. A.; Booth, B. L. The chemistry of diaminomaleonitrile and its utility in heterocyclic synthesis. Tetrahedron, 2003, 59, 2749-2763.
    • (2003) Tetrahedron , vol.59 , pp. 2749-2763
    • Al-Azmi, A.1    Elassar, A.-Z.A.2    Booth, B.L.3
  • 32
    • 0023385987 scopus 로고
    • Rules for Optimization of Biocatalysis in Organic Solvents
    • Laane, C.; Boeren, S.; Vos, K.; Veeger, C. Rules for Optimization of Biocatalysis in Organic Solvents. Biotechnol. Bioeng., 1987, 30, 81-87.
    • (1987) Biotechnol. Bioeng , vol.30 , pp. 81-87
    • Laane, C.1    Boeren, S.2    Vos, K.3    Veeger, C.4
  • 33
    • 10044220927 scopus 로고    scopus 로고
    • Highly Enantioselective Acylation of rac-Alkyl Lactates Using Candida antarctica Lipase B
    • Lee, Y. S.; Hong, J. H.; Jeon, N. Y.; Won, K.; Kim, B. T. Highly Enantioselective Acylation of rac-Alkyl Lactates Using Candida antarctica Lipase B. Org. Process Res. Dev., 2004, 8, 948-951.
    • (2004) Org. Process Res. Dev , vol.8 , pp. 948-951
    • Lee, Y.S.1    Hong, J.H.2    Jeon, N.Y.3    Won, K.4    Kim, B.T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.