The catalytic activity of lipases toward hydroxy fatty acids - A review

JAOCS, Journal of the American Oil Chemists' Society

Volumn 73, Issue 5, 1996, Pages 543-549

  Hayes, Douglas G ^a,b  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

^b The University of Alabama in Huntsville   (United States)

Author keywords

Enantioselectivity; Estolides; Hydroxy fatty acids; Lactones; Lipases

Indexed keywords

ALCOHOLS; BACTERIA; CATALYSIS; DERIVATIVES; ENZYMES; ESTERIFICATION; ESTERS; INORGANIC ACIDS; MOLECULES;

ENANTIOSELECTIVITY; ESTOLIDES; HYDROXY FATTY ACIDS; LACTONES; LIPASES; STEREOSELECTIVITY;

FATTY ACIDS;

EID: 0030148149     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02518105     Document Type: Review

References (66)

1. Smith Jr. C.R., Occurrence of Unusual Fatty Acids in Plants, in The Chemistry of Fats and Other Lipids, edited by R.T. Holman, Pergamon Press, Oxford, 1970, pp. 139-177.
2. Esaki, N., S. Ito, W. Blank, and K. Soda, Biotransformation of Oleic Acid by Alcaligenes sp. 5-18, a Bacterium Tolerant to High Concentrations of Oleic Acid, J. Ferment Bioeng. 77:148-151 (1994).
3. Hayes, D.G., R. Kleiman, and B.S. Phillips, The Triglyceride Composition, Structure, and Presence of Estolides in the Oils of Lesquerella and Related Species, J. Am. Oil Chem. Soc. 72:559-569 (1995).
4. Morrison, R.T., and R.N. Boyd, Organic Chemistry (4th edn.), Allyn and Bacon, Boston, 1983.
5. Gutman, A.L., D. Oren, A. Boltanski, and T. Bravdo, Enzymaztic Oligomerisation Versus Lactonisation of ω-Hydroxyesters, Tetrahed. Lett. 28:5367-5368 (1987).
6. Gatfield, I.L., The Enzymatic Synthesis of Esters in Nonaqueous Systems, Ann. NY Acad. Sci. 434:569-512 (1984).
7. Gutman, A.L., K. Zuobi, and T. Bravdo, Lipase-Catalyzed Preparation of Optically Active γ-Butyrolactones in Organic Solvents, J. Org. Chem. 55:3546-3552 (1990).
8. Santaniello, E., P. Ferraboschi, and P. Grisenti, Lipase-Catalyzed Transesterification in Organic Solvents: Applications to the Preparation of Enantiomerically Pure Compounds, Enzyme Microb. Technol. 15:367-382 (1993).
9. Huffer, M., and P. Schreier, Lipase-Catalyzed Transesterification in Organic Solvents: Preparation and Enantiodifferentiation of Optically Enriched 4 (5)-Alkylated 1,4 (1,5)-Olides, Tetrahed. Assym. 2:1157-1164 (1991).
10. Knani, D., A.L. Gutman, and D.H. Kohn, Enzymatic Polyesterification in Organic Media. Enzyme-Catalyzed Synthesis of Linear Polyesters. I. Condensation Polymerization of Linear Hydroxy Esters. II. Ring-Opening Polymerization of ε-Caprolactone, J. Polym. Sci.: Pt. A.: Polym Chem. 31:1221-1232 (1993).
11. Yamada, H., T. Sugai, H. Ohta, and S. Yoshikawa, Simple Synthesis of (R)-5-Hexadecanolide, Agric. Biol. Chem. 54:1579-1580 (1990).
12. Bonini, C., P. Pucci, R. Racioppi, and L. Viggiani, Enzyme Catalysed Lactonization of 3,5 Dihydroxy esters: Enantioselective Synthesis of Naturally Occurring 3-Hydroxy-5-Decanolide, (-)-Massoialactone, and 3-Hydroxy-5-Icosanolide, Tetrahed. Assym. 3:29-32 (1992).
13. Uyama, H., and S. Kobayashi, Enzymatic Ring-Opening Polymerization of Lactones Catalyzed by Lipase, Chem. Lett. 1993:1149-1150 (1993).
14. Zhi-wei, G., T.K. Ngooi, A. Scilimati, G. Fulling, and C.J. Sih, Macrocyclic Lactones via Biocatalysis in Non-Aqueous Media, Tetrahed. Lett. 29:5583- (1988).
15. Kageyama, Y., T. Nihira, and Y. Yamada, Lipase-Catalyzed Synthesis of Macrocyclic Lactones in Organic Solvents, Ann. NY Acad. Sci. 613:681-685 (1990).
16. Makita, A., T. Nihara, and Y. Yamada, Lipase catalyzed synthesis of macrocyclic lactones in organic solvents, Tetrahed. Lett. 25:805-808 (1987).
17. Antczak, U., J. Gora, T. Antczak, and E. Gala, Enzymatic lactonization of 15-hydroxypentadecanoic and 16-hydroxyhexadecanoic acids to macrocyclic lactones, Enzyme Microb. Technol. 13:589-593 (1991).
18. Yamada, H., S. Ohsawa, T. Sugai, H. Ohta, and S. Yoshikawa, Lipase-Catalyzed Highly Enantioselective Macrolactonization of Hydroxyacid Esters in an Organic Solvent, Chem. Lett. 1775-1776 (1989).
19. Rees, G.D., T.R. Jenta, M.G. Nascimento, M. Catauro, B.H. Robinson, G.R. Stephenson, and R.D.G. Olphert, Use of Water-in-Oil Microemulsions and Gelatin-Containing Microemulsion-Based Gels for Lipase-Catalysed Ester Synthesis in Organic Solvents, Indian J. Chem. 32B:30-34 (1993).
20. Yamane, T., Y. Kojima, T. Ichiryu, M. Nagata, and S. Shimizu, Intramolecular Esterification by Lipase Powder in Microaqueous Benzene: Effect of Moisture Content, Biotechnol. Bioeng. 34:838-843 (1989).
21. Kodera, Y., M. Furukawa, M. Yokoi, H. Kuno, H. Matsushita, and Y. Inada, Lactone Synthesis from 16-Hydroxyhexadecanoic Acid Ethyl Ester in Organic Solvents Catalyzed with Polyethylene Glycol-Modified Lipase, J. Biotechnol. 31:219-224 (1993).
22. Robinson, G.K., M.J. Alston, C.J. Knowles, and K.R. Motion, An Investigation into the Factors Influencing Lipase-Catalyzed Intramolecular Lactonization in Microaqueous Systems, Enzyme Microb. Technol. 16:855-863 (1994).
23. Ajima, A., T. Yoshimoto, K. Takahashi, Y. Tamaura, Y. Saito, and Y. Inada, Polymerization of 10-Hydroxydecanoic Acid in Benzene with Polyethylene Glycol-Modified Lipase, Biotechnol. Lett. 7:303-306 (1985).
24. Rees, G.D., B.H. Robinson, and G.R. Stephenson, Macrocyclic Lactone Synthesis by Lipases in Water-in-Oil Microemulsions, Biochem. Biophys. Acta. 1257:239-248 (1995).
25. Matsumura, S., and J. Takahashi, Makromol. Enzymatic Synthesis of Functional Oligomers, 1. Lipase Catalyzed Polymerization of Hydroxy Acids, Makromol. Chem. Rapid Comm. 7:369-373 (1986).
26. O'Hagan, D., and N.A. Zaidi, Enzyme-Catalysed Condensation Polymerization of 11-Hydroxyundecanoic Acid with Lipase from Candida cylindracea, Polymer 35:3576-3578 (1994).
27. Uyama, H., K. Takeya, and S. Kobayashi, Enzymatic Ring-Opening Polymerization of Lactones to Polyesters by Lipase Catalyst: Unusually High Reactivity of Macrolides, Bull. Chem. Soc. Jpn. 68:56-61 (1995).
28. Lobell, M., and M.P. Schneider, Lipase Catalyzed Formation of Lactones via Irreversible Intramolecular Acyltransfer, Tetrahed. Assym. 4:1027-1030 (1993).
29. Yamane, T., Recent Developments in Lipase-Catalyzed Biotransformations of Fats and Oils, INFORM 4:481 (1993).
30. Okumura, S., M. Iwai, and Y. Tsujisaka, Synthesis of Estolides During Hydrolysis of Castor Oil by Geotrichum candidum Lipase. Yukagaku 32:271-213 (1983).
31. Yamaguchi, C., A. Tooyama, S. Asaoka, and F. Osada, Manufacture of Glycerin-Free Estolides from Castor Oil with Lipase, Japanese Patent 9013387 (1989).
32. Yamaguchi, C., M. Akita, S. Asaoka, and F. Osada, Enzymic Manufacture of Castor-Oil Fatty Acid Estolides, Japanese Patent 8916591 (1988).
33. Yoshida, Y., and M. Kawase, Enzymatic Synthesis of Estolides by a Continuous Reactor. INFORM 3, 1992.
34. Hayes D.G., and R. Kleiman, Lipase-Catalyzed Synthesis and Properties of Estolides and Their Esters, J. Am. Oil Chem. Soc. 72:1309-1316 (1995).
35. O'Hagan, D., and N.A. Zaidi, Polymerisation of 10-Hydroxydecanoic Acid with the Lipase from Candida cylindracea, J. Chem. Soc. Perkin Trans. I:2389-2390 (1993).
36. Nomura, R., A. Ueno, and T. Endo, Anionic Ring-Opening Polymerization of Macrocyclic Esters, Macromolecules 27:620-621 (1994).
37. Gutman, A.L., K. Zuobi, and A. Boltansky, Enzymatic Lactonisation of γ-Hydroxyesters in Organic Solvents. Synthesis of Optically Pure γ-Methylbutyrolactones and γ-Phenylbutyrolactone, Tetrahed. Lett. 25:3861-3864 (1987).
38. Gutman, A.L., and T. Bravdo, Enzyme-Catalyzed Enantioconvergent Lactonization of γ-Hydroxy diesters in Organic Solvents, J. Org. Chem. 54:4263-4265 (1989).
39. Bonini, C., P. Pucci, and L. Viggiani, A Remarkable Short Synthesis of Optically Active Mevinic Acid Analogues by Biocatalytic Lactonization of syn-3,5-Dihydroxy Esters, J. Org. Chem. 56:4050-4052 (1991).
40. Sugai, T., and H. Ohta, Lipase-Catalyzed Kinetic Resolution of 2-Hydroxyhexadecanoic Acid and Its Esters, Agric. Biol. Chem. 54:3337-3338 (1990).
41. Sugai, T., and H. Ohta, Enzymatic Preparation of Ethyl (S)-3-Hydroxybutanoate with a High Enantiomeric Excess, Agric. Biol. Chem. 53:2009-2010 (1989).
42. Bornscheuer, U., A. Herar, A. Capewell, V. Wendel, L. Kreye, T. Scheper, E. Vob, K. Wünsche, and H.H. Meyer, Lipase-Catalyzed Kinetic Resolution of 3-Hydroxy Esters: Optimization, Batch, and Continuous Reactions, Ann. N.Y. Acad. Sci. 750:215-221 (1995).
43. Sugai, T., S. Ohsawa, H. Yamada, and H. Ohta, Preparation of Enantiomerically Enriched Compounds Using Enzymes; VII. A Synthesis of Japanese Beetle Pheromone Utilizing Lipase-Catalyzed Enantioselective Lactonization, Synthesis:1112-1114 (1990).
44. Blanco, L., E. Guibe-Jampel, and G. Rousseau, Enzymatic Resolution of Racemic Lactones, Tetrahed. Lett. 29:1915-1918 (1988).
45. Mori, K., Synthesis of Optically Active Pheromones, Tetrahedron 45:3233-3298 (1989).
46. Ghoshray, S., and D.K. Bhattacharya, Enzymatic Preparation of Ricinoleic Acid Esters of Long-Chain Monohydric Alcohols and Properties of the Esters, J. Am. Oil Chem. Soc. 69:85-88 (1992).
47. Feichter C., K. Faber, and H. Griengl, Biocatalytic Resolution of Long-Chain 3-Hydroxyalkanoic Esters, Tetrahed. Lett. 30:551-552 (1989).
48. Hönig, H., P. Sevfer-Wassenthal, and H. Webber, Simultaneous Separation of Enantiomers of Diastereomers by Lipases, Tetrahed. Lett. 31:3011-3012 (1990).
49. Scilimati, A., T.K. Ngooi, and C.J. Sih, Biocatalytic Resolution of ± Hydroxyalkanoic Esters. A Strategy for Enhancing the Enantiomeric Specificity of Lipase-Catalyzed Ester Hydrolysis, Tetrahed. Lett. 29:4927-4930 (1988).
50. Bevinakatti, H.S., A.A. Banerji, and R.V. Newadkar, Resolution of Secondary Alcohols Using Lipase in Diisopropyl Ether, J. Org. Chem. 54:2453-2455 (1989).
51. Tokiwa, Y., T. Ando, T. Suzuki, and T. Takeda, Biodegradation of Synthetic Polymers Containing Ester Bonds, Polymer Mater. Sci. Engr. 62:988-992 (1990).
52. Mochizuki, M., M. Hirano, Y. Kanmuri, K. Kudo, and Y. Tokiwa , Hydrolysis of Polycaprolactone Fibers by Lipase: Effects of Draw Ratio on Enzymatic Degradation, J. Appl. Polym. Sci. 55:289-296 (1995).
53. Chen, C.S., S.H. Wu, G. Girdaukas, and C.J. Sih, Quantitative Analyses of Biochemical Kinetic Resolution of Enantiomers. 2. Enzyme-Catalyzed Esterifications in Water-Organic Solvent Biphasic Systems, J. Am. Chem. Soc. 109:2812-2817 (1987).
54. Vorderwülbecke, T., K. Kieslich, and H. Erdmann, Comparison of Lipases by Different Assays, Enzyme Microb. Technol. 14:631-639 (1992).
55. Sonnet, P.P., and J.A. Gazzillo, Evaluation of Lipase Selectivity for Hydrolysis, J. Am. Oil Chem. Soc. 68:11-15 (1991).
56. Engel K.H., M. Bohnen, and M. Dobe, Lipase-Catalysed Reactions of Chiral Hydroxyacid Esters: Competition of Esterification and Transesterification, Enzyme Microb. Technol. 13:655-660 (1991).
57. Chattopadhyay, S., and V.R. Mamdapur, Enzymatic Esterification of 3-Hykdroxybutyric Acid, Biotechnol. Lett. 15:245-250 (1993).
58. Steffen, B., A. Ziemann, S. Lang, and F. Wagner, Enzymatic Monoacylation of Trihydroxy Compounds, Biotechnol. Lett. 14:773-778 (1992).
59. Mukesh, D., R.S. Iyer, J.S. Wagh, A.A. Makashi, A.A. Banerji, R.V. Newaskar, and H.S. Bevinakatti, Lipase Catalysed Transesterification of Castor Oil, Biotechnol. Lett. 15:251-256 (1993).
60. Wagner, F., F. Kleppe, W. Lokotsch, A. Ziemann, and S. Lang, Synthesis of Uncommon Wax Esters with Immobilized Lipases, Ann. NY Acad. Sci. 672:484-491 (1992).
61. Lang, S., R. Multzsch, A. Passeri, A. Schmeichel, B. Steffen, F. Wagner, D. Hamann, and H.K. Cammenga, Unusual Wax Esters and Glycolipids: Biocatalytical Formation and Physico-Chemical Characterization, Acta Biotechnol. 11:379-386 (1991).
62. Oldfield, C., G.D. Rees, B.H. Robinson, and R.B. Freedman, Enzyme Action and Enzyme Reversal in Water-in-Oil Microemulsions, in C. Laane, J. Tramper, and M.D. Lilly editors, Biocatalysis in Organic Media, Elsevier, Amsterdam, 1987, pp. 119-123.
63. Lu, Y., C. Miet, N. Kunesch, and J.E. Poisson, A Simple Total Synthesis of (S)-Isoserine, Tetrahed. Assym. 2:871-872 (1991).
64. Multzsch, R., W. Lokotsch, B. Steffen, S. Lang, J.O. Metzger, H.J. Schäfer, S. Warwel, and F. Wagner, Enzymatic Production and Physicochemical Characterization of Uncommon Wax Esters and Monoglycerides, J. Am. Oil Chem. Soc. 71:721-725 (1994).
65. Hayes, D.G., and R. Kleiman, Lipase-Catalyzed Synthesis of Lesquerolic Acid Wax and Diol Esters and Their Properties, J. Am. Chem. Soc. in press.
66. Parida, S., and J.S. Dordick, Substrate Structure and Solvent Hydrophobicity Control Lipase Catalysis and Enantioselectivity in Organic Media, J. Am. Chem. Soc. 113:2253-2259 (1991).