Recent advances in the use of immobilized lipases directed toward the asymmetric syntheses of complex molecules

Biocatalysis and Biotransformation

Volumn 13, Issue 3, 1996, Pages 141-156

  Akita, Hiroyuki ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

Enantioselective hydrolysis; Immobilization with Celite; Immobilized lipase; Phospholipid lipase aggregate; Prepolymer method

Indexed keywords

EID: 0001492817     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.3109/10242429608997671     Document Type: Article

References (34)

1. Akita, H., Enoki, Y., Yamada, H., and Oishi, T., (1989) Enzymatic Hydrolysis in Organic Solvents for Kinetic Resolution of Water-Insoluble α-Acyloxy Esters with Immobilized Lipases. Chem. Pharm. Bull., 37, 2876-2878
2. Akita, H., Umezawa, I., Matsukura, H., and Oishi, T., (1991) A Lipid-Lipase Aggregate As a New Type of Immobilized Enzyme., Chem. Pharm. Bull., 39, 1632-1633
3. Akita, H., Umezawa, I., Matsukura, H., and Oishi, T., (1992) A Lipid-Lipase Aggregate with Ether Linkage as a New Type of Immobilized Enzyme for Enantioselective Hydrolysis in Organic Solvents. Chem. Pharm. Bull., 40, 318-324
4. Akita, H., Umezawa, I., Sakurai, I., and Oishi, T., (1993) Structural Characteristics of Lipid-Lipase Aggregates for Enantioselective Hydrolysis in Organic Solvents. Chem. Pharm. Bull., 41, 12-15
5. Akita, H., Umezawa, I., Tisnadjaja, D., Matsukura, H., and Oishi, T., (1993) Enantioselective Actylation of an α-Hydroxy Ester by Using Ether-Linked Lipid-Lipase Aggregates in Organic Solvents. Chem. Pharm. Bull., 41, 16-20
6. Akita, H., Umezawa, I., Nozawa, M., Nagumo, S., (1993) Total Synthesis of (-)-Oudemansin X Based on Enzymatic Resolution Using Immobilized Lipase. Tetrahedron:Asymmetry, 4, 757-760
7. Cambou, B., and Klibanov, A.M., (1984) Preparative Production of Optically Active Esters and Alcohols Using Esterase-Catalyzed Stereospecific Transesterification in Organic Media. J. Am. Chem. Soc., 106, 2687-2692
8. Franks, N.P., (1976) Structural Analysis of Hydrated Egg Lecithin and Cholesterol Bilayers. J. Mol. Biol., 100, 345-358
9. Fukui, S., and Tanaka, A., (1984) Application of Biocatalysts Immobilized by Prepolymer Methods. Advances in Biochemical Engineering/Biotechnology, 29, 1-33
10. Guibe-Jampel, E., and Rousseau, G., (1987) Selectively in the transesterification of esters by supported enzymes. Tetrahedron Lett., 28, 3563-3564
11. Hauser, H., Pascher, I., Pearson, R.H., and Sundell S., (1981) Preferred Conformation and Molecular Packing of Phosphatidylethanolamine and Phosphatidylcholine. Biochim. Biophys. Acta, 650, 21-51
12. Hoshino, O., Itoh, K., Umezawa, B., Akita, H., and Oishi, T., (1988) Immobilized Lipases Catalyzed Hydrolysis of Labile Acetate: Enantioselective Hydrolysis of (±)-4-Acetoxy- 1,2,3,4-Tetrahydro-6,7-Dimethoxy-2-Methylisoquinoline. Tetrahedron Lett., 29, 567-568
13. Hoshino, O., Itoh, K., Umezawa, B. (deceased), Akita, H., and Oishi, T., (1990) Kinetic Resolution of (±)-4-Acyloxy-1,2,3,4-tetrahydro-6.7-dimethoxy-2-methylisoquinolines by Use of Immobilized Lipases in Organic Solvents. Chem. Pharm. Bull., 38, 3273-3276
14. Hoshino, O., Itoh, K., Tanahashi, R., Umezawa, B. (deceased), Akita, H., and Oishi, T., (1990) Revised Stereostructure for (+)-Roemecarine and Synthesis of (±)-, (+)-, nad (-)-Roemercarine and (±)-Epiroemecarine. Chem. Pharm. Bull., 38, 3277-3279
15. Hoshino, O., Tanahashi, R., Okada, M., Akita, H., and Oishi, T., (1993) Enzymatic Resolution of Acylates of Prochiral Phenolic 1-Aryl- and 1-Arylalkyl- 1,2,3,4-tetrahydroisoquinolinols, which possess a Guaiacol-type Moiety, by use of Immobilized Lipase in Organic Solvent. Tetrahedron: Asymmetry, 4, 933-942
16. Hsu, Shu-Hui, Wu, Shihn-Sheng, Wang, Yi-Fong, and Wong, Chi-Huey, (1990) Lipase-Catalyzed Irreversible Transesterification Using Enol Esters: XAD-8 Immobilized Lipoprotein Lipase-Catalyzed Resolution of Secondary Alcohols. Tetrahedron Lett., 31, 6403-6406
17. 4 Antagonist. Tetrahedron:Asymmetry, 4, 865-874
18. Ihara, M., Suzuki, M., Fukumoto, K., and Kabuto, C., (1990) Asymmetric Total Synthesis of Atisine via Intramolecular Double Michael Reaction. J. Am. Chem. Soc., 112, 1164-1171
19. Koshiro, S., Sonomoto, K., Tanaka, A., and Fukui, S., (1985) Stereoselective esterification of dl-menthol by polyurethane-entrapped lipase in organic solvent. J. of Biotechnology, 2, 47-57
20. Laumen, K., Reimerdes, E.H., and Schneider, M., (1985) Immobilized Porcine Liver Esterase: A Convenient Reagent for the Preparation of Chiral Building Blocks. Tetrahedron Lett., 26, 407-410
21. Luthi, P., and Luisi, P.L., (1984) Enzymatic Synthesis of Hydrocarbon-Soluble Peptides with Reverse Micelles. J. Am. Chem. Soc., 106, 7285-7286
22. Morita, S., Narita, H., Matoba, T., and Kito, M., (1984) Synthesis of Triacylglycerol by Lipase in Phosphatidylcholine Reverse Micellar System. J. Am. Oil Chem. Soc., 61, 1571-1574
23. Okahata, Y., Fujimoto, Y., and Ijiro, K., (1988) Lipase-Lipid Complex as A Resolution Catalyst of Racemic Alcohols in Organic Solvents. Tetrahedron Lett., 29, 5133-5134
24. Okahata, Y., and Ijiro, K., (1988) A Lipid-coated Lipase as a New Catalyst for Triglyceride Synhesis in Organic Solvents. J. Chem. Soc, Chem, Commun., 1392-1394
25. Pottie, M., Van der Eycken, J., and Vandewalle, M., (1989) Enzymatic Enantioselective Hydrolysis of 2,2-Dimethyl-1,3-Dioxolane-4-Carboxylic Esters. Tetrahedron Lett., 30, 5319-5322
26. Sakurai, I., Iwayanagi, S., Sakurai, T., Seto, T., (1977) X-ray Study on Egg-yolk Lecithin: Unit Cell Data and Electron Density Profile. J. Mol. Biol., 117, 285-291
27. Sakurai, I., Sakurai, T., Seto, T., and Iwayanagi, S., (1983) Lyotropic Phase Transitions in Single Crystals of L-And DL-Dipalmitoylglycerophosphocholines. Chem. Phys. Lipids, 32, 1-11
28. Sugiura, M., Oikawa, T., Hirano, K., and Inukai, T., (1977) Purification, Crystallization and Properties of Triacylglycerol Lipase from Pseudomonas fluorescens. Biochim. Biophys. Acta, 488, 353-358
29. Takahashi, K., Ajima, A., Yoshimoto, T., Okada, M., Matsushima, A., Tamaura, Y, and Inada, Y., (1985) Chemical Reactions by Polyethylene Glycol Modified Enzymes in Chlorinated Hydrocarbons. J. Org. Chem., 50, 3415-3416
30. Takahata, H., Uchida, Y., and Momose, T., (1992) Transesterification-Based Enzymatic Resolutions of Racemic 3-Hydroxy-4-pentenylurethanes in Organic Solvents. Tetrahedron Lett., 33, 3331-3332
31. Takahata, H., Uchida, Y., Ohkawa, Y., and Momose, T., (1993) Enzymatic Resolution of N,N-Dialkyl-3-hydroxy-4-pentenamides, Unsuccessful in Resolution of the Katsuki-Sharpless Asymmetric Epoxidation. Tetrahedron:Asymmetry, 4, 1041-1042
32. Tardieu, A., Luzzati, V. and Reman, F. C., (1973) Structure and Polymorphism of the Hydrocarbon Chains of Lipids: A Study of Lecithin-Water Phases. J. Mol. Biol., 75, 711-733
33. Terao, Y., Tsuji, K., Murata, M., Achiwa, K., Nishio, T., Watanabe, N., and Seto, K. (1989) Facile Process for Enzymatic Resolution of Racemic Alcohols. Chem. Pharm. Bull., 37, 1653-1655
34. Tombo, G.M.R., Schar, H,-P., Fernandez, X., Busquets, I., and Ghisalba, O., (1986) Synthesis of Both Enantiomeric Forms of 2-Substituted 1,3-Propanediol Monoacetates Starting from A Common Prochiral Precursor, Using Enzymatic Transformations in Aqueous and in Organic Media. Tetrahedron Lett., 27, 5707-5710