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Volumn 62, Issue 15, 1997, Pages 4906-4907

Enhancement of the Enantioselectivity in Lipase-Catalyzed Kinetic Resolutions of 3-Phenyl-2H-azirine-2-methanol by Lowering the Temperature to -40°C

Author keywords

[No Author keywords available]

Indexed keywords

TRIACYLGLYCEROL LIPASE;

EID: 0030800148     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970581j     Document Type: Article
Times cited : (121)

References (39)
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    • For example: (a) Jones, J. B. Tetrahedron 1986, 42, 3351. (b) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695. (c) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114. (d) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994. (e) Enzyme Catalysis in Organic Synthesis; Drauz, K., Waldmann, H., Eds.; VCH: New York, 1994; Vol. 1. (f) Faber, K. Biotransformations in Organic Chemistry; Springer-Verlag: Berlin, 1995. (g) Enzymatic Reactions in Organic Media; Koskinen, A. M. P., Klibanov, A. M., Eds.; Blackie Academic: Glasgow, 1996.
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    • For example: (a) Yokomatsu, T.; Sato, M.; Shibuya, S. Tetrahedron: Asymmetry 1996, 7, 2743. (b) Hirose, Y.; Kariya, K.; Sasaki, I.; Kurono, Y.; Ebiike, H.; Achiwa, K. Tetrahedron Lett. 1992, 33, 7157. (c) Fuji, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y. Tetrahedron Lett. 1990, 31, 6663.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7157
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    • For example: (a) Yokomatsu, T.; Sato, M.; Shibuya, S. Tetrahedron: Asymmetry 1996, 7, 2743. (b) Hirose, Y.; Kariya, K.; Sasaki, I.; Kurono, Y.; Ebiike, H.; Achiwa, K. Tetrahedron Lett. 1992, 33, 7157. (c) Fuji, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y. Tetrahedron Lett. 1990, 31, 6663.
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    • Lowowski, W., Ed.; Pergamon Press: New York, Chapter 5
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  • 34
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    • note
    • Lipases showing the E values > 3 (origin, E value, fast-reacting enantiomer): CHIRAZYME L-2 (Candida antarctica, 8, R),CHIRAZYME L-7 (poreine pancreas, 6, R), lipase AK (Pseudomonas fluorescens, 4, R).
  • 36
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    • note
    • 2O (11), benzene (9), cyclohexane (9), n-hexane (7).
  • 38
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    • note
    • When the temperature was decreased below -40°C, the lipase might begin to lose the conformational flexibility essential for the catalytic activity.
  • 39
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    • Lipase exhibits a high catalytic activity on heating at 100°C: Zaks, A.; Klibanov, A. M. Science 1984, 224, 1249.
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