Practical enzymatic resolution of racemic alcohols and amines in organic solvents

Annals of the New York Academy of Sciences

Volumn 799, Issue , 1996, Pages 620-632

  Gutman, Arie L ^a   Shkolnik, Eleonora ^a   Meyer, Elazar ^a   Polyak, Felix ^a   Brenner, Dov ^a   Boltanski, Aviv ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; ENZYME; ORGANIC SOLVENT;

ACYLATION; CHIRALITY; CONFERENCE PAPER; ENZYME MECHANISM; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030463413     PISSN: 00778923     EISSN: None     Source Type: Book Series    
DOI: 10.1111/j.1749-6632.1996.tb33267.x     Document Type: Conference Paper

References (25)

1. WONG, C-H. & G. M. WHITESIDES. 1994. Enzymes in Synthetic Organic Chemistry. First edition. Tetrahedron Organic Chemistry Series. Volume 12. Pergamon. Elmsford, New York.
2. (a) CHEN, C-S. & C. J. SIH. 1989. General aspects and optimization of enantioselective biocatalysis in organic solvents: the use of lipases. Angew. Chem. Int. Ed. Engl. 28: 695-707;
3. (b) KLIBANOV, A. M. 1990. Asymmetric transformations catalyzed by enzymes in organic solvents. Ace. Chem. Res. 23: 114-120;
4. GUTMAN, A. L. & M. SHAPIRA. 1995. Synthetic applications of enzymatic reactions in organic solvents. In Advances in Biochemical Engineering/Biotechnology. Volume 52. Springer-Verlag. Berlin/New York.
5. (a) KIRCHNER, G., M. P. SCOLLAR & A. M. KLIBANOV. 1985. Resolution of racemic mixtures via lipase catalysis in organic solvents. J. Am. Chem. Soc. 107: 7072-7076;
6. (b) for recent reviews, also see reference 2c above.
7. (a) GUTMAN, A. L., K. ZUOBI & A. BOLTANSKI. 1987. Enzymatic lactonization of γ-hydroxyesters in organic solvents: synthesis of optically pure γ-methylbutyrolactone and γ-phenylbutyrolactone. Tetrahedron Lett. 28: 3861-3864;
8. (b) MAKITA, A., T. NIHIRA & Y. YAMADA. 1987. Lipase-catalyzed synthesis of macrocyclic lactones in organic solvents. Tetrahedron Lett. 28: 805-808;
9. GUO, Z-W. & C. J. SIH. 1988. Enzymatic synthesis of macrocyclic lactones. J. Am. Chem. Soc. 110: 1999-2001;
10. Guo, Z-W., T. K. NGOOI, A. SCILIMATI, G. FULLING & C. J. SIH. 1988. Macrocyclic lactones via biocatalysis in non-aqueous media. Tetrahedron Lett. 29: 5583-5586;
11. (e) GUTMAN, A. L. & T. BRAVDO. 1989. Enzyme-catalyzed enantioconvergent lactonization of γ-hydroxy diesters in organic solvents. J. Org. Chem. 5-4: 4263-4265;
12. (f) GUTMAN, A. L., K. ZUOBI & T. BRAVDO. 1990. Lipase-catalyzed preparation of optically active γ-butyrolactones in organic solvents. J. Org. Chem. 55: 3546-3552.
13. (a) GUTMAN, A. L., D. OREN, A. BOLTANSKI & T. BRAVDO. 1987. Enzymatic oligomerization versus lactonization of ω-hydroxyesters. Tetrahedron Lett. 28: 5367-5368;
14. (b) MARGOLIN, A. L., J-Y. CRENNE & A. M. KLIBANOV. 1987. Stereoselective oligomerizations catalyzed by lipases in organic solvents. Tetrahedron Lett. 28: 1607-1610;
15. WALLACE, J. S. & C. J. MORROW. 1989. Biocatalytic synthesis of polymers: synthesis of an optically active, epoxy-substituted polyester by lipase-catalyzed polymerization. J. Polym. Sci. Part A 27: 2553-2567;
16. GUTMAN, A. L. & T. BRAVDO. 1989. Enzyme-catalyzed enantioconvergent polymerization of β-hydroxyglutarate in organic solvents. J. Org. Chem. 54: 5645-5646;
17. (e) KNANI, D., A. L. GUTMAN & D. KOHN. 1993. Enzymatic polyesterification in organic media: enzyme-catalyzed synthesis of linear polyesters. J. Polym. Sci. Part A 31: 1221-1232.
18. ZAKS, A. & A. M. KLIBANOV. 1985. Enzyme-catalyzed processes in organic solvents. Proc. Natl. Acad. Sci. U.S.A. 82: 3192-3196.
19. KITAGUCHI, H., P. A. FITZPATRICK, J. E. HUBER & A. M. KLIBANOV. 1989. Enzymatic resolution of racemic amines: crucial role of the solvent. J. Am. Chem. Soc. 111: 3094-3095.
20. GUTMAN, A. L., E. MEYER, X. YUE & C. ABELL. 1992. Enzymatic formation of lactams in organic solvents. Tetrahedron Lett. 33: 3943-3946.
21. GUTMAN, A. L., D. BRENNER & A. BOLTANSKI. 1993. Convenient practical resolution of racemic alkyl-aryl alcohols via enzymatic acylation with succinic anhydride in organic solvents. Tetrahedron Asymmetry 4: 839-844.
22. SHKOLNIK, E. & A. L. GUTMAN. 1994. Resolution of racemic sterically hindered secondary alcohols via enzymatic alcoholysis of their esters: the first enzymatic preparation of optically pure 2,2,2-trifluoro-1-(9-anthryl)ethanol. J. Bioorg. Med. Chem. 2: 567-572.
23. YOUDIM, M. B. H., J. P. FINBERG & K. F. TIPTON. 1988. Monoiminooxidases. In Handbook of Experimental Pharmacology. Volume 90/I, chapter 3, p. 121-197. Springer-Verlag. Berlin/New York.
24. YOUDIM, M. B. H., J. P. M. FINBERG, R. LEVY, J. STERLING, D. LERNER & T. BERGER-PASKIN. 1991. European patent application no. 91100081.8.
25. GUTMAN, A. L., E. MEYER, E. KALERIN, F. POLYAK & J. STERLING. 1992. Enzymatic resolution of racemic amines in a continuous reactor in organic solvents. Biotechnol. Bioeng. 40: 760-767.