Application of lipase-catalyzed transformations for the synthesis of insect pheromones and related compounds

Journal of Molecular Catalysis B: Enzymatic

Volumn 2, Issue 6, 1997, Pages 257-269

  Fukusaki, Eiichiro ^a   Satoda, Shiro ^b  

^a OSAKA UNIVERSITY   (Japan)

^b NITTO DENKO CORPORATION   (Japan)

Author keywords

Acylation; Enantioselective; Enzyme; Lipase; Optical resolution; Sex pheromone; Transesterification

Indexed keywords

ACRYLIC MONOMERS; ACYLATION; ALCOHOLS; CATALYSIS; COMPOSITION EFFECTS; ENZYMES; ESTERIFICATION; KETONES; OPTICAL RESOLVING POWER; ORGANIC POLYMERS; SYNTHESIS (CHEMICAL);

ENANTIOMERS; INSECT PHEROMONES; LIPASE CATALYZED TRANSFORMATIONS; TRANSESTERIFICATION;

HORMONES;

EID: 0031123832     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1177(96)00027-6     Document Type: Review

References (95)

1. A.M. Klibanov, Acc. Chem. Res., 23 (1990) 114-120.
2. C. Wong, Science, 244 (1990) 1145-1152.
3. C. Wong and G.M. Whitesides, Use of hydrolytic enzymes: amidases, proteases, esterases, lipases, nitriases, phosphatases, epoxide hydrolases, in: Enzymes in Synthetic Organic Chemistry, 70-107, 1994.
4. Y. Kageyama, T. Nihira and Y. Yamada, Enzyme Engineering 10, 613 (1990) 681-685.
5. M. Nishizawa, M. Yamada and R. Noyori, Tetrahedron Lett., 22 (1981) 247-250.
6. M.M. Midland and A. Tramontano, Tetrahedron Lett., 21 (1980) 3549-3552.
7. S. Yamaguchi and H.S. Mosher, J. Org. Chem., 38 (1973) 1870-1877.
8. R.S. Brinkmeyer and V.M. Kapoor, J. Am. Chem. Soc., 99 (1977) 8339-8341.
9. S. Senda and K. Mori, Agric. Biol. Chem., 47 (1983) 2595-1598.
10. K.A. Parker, J. Org. Chem., 61 (1996) 3214-3217.
11. E.J. Corey and C.J. Helal, Tetrahedron Lett., 37 (1996) 4837-4840.
12. S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya and R. Noyori, J. Am. Chem. Soc., 117 (1995) 7562-7563.
13. J.H. Tumlinson, M.G. Kleinn, R. Doolittle, T.T. Ladd and A.T. Proveaux, Science, 197 (1977) 789-792.
14. W.S. Leal, Naturwissenschaften, 78 (1991) 521-523.
15. B.A. Bierl, M. Beroza and C.W. Collier, Science, 170 (1970) 87-89.
16. Behavior-modifying chemicals for insect management, 1990.
17. P.J. Shea, ACS Symp. Ser., 595 (1995) 272-283.
18. J. Vrkoc, Chem. Scr., 29 (1989) 407-410.
19. Y. Tamaki, Natl. Inst. Agric. Sci., Japan, 37 (1980) 22-25.
20. K. Mori, The synthesis of pheromones, in: The total synthesis of natural products, 9, 1992, pp. 1-534.
21. R.E. Doolittle, J.H. Tumlinson, AT. Proveaux and R.R. Heath, J. Chem. Ecol., 6 (1980) 473-485.
22. W.H. Pirkle and P.E. Adams, J. Org. Chem., 44 (1979) 2169-2175.
23. K. Sato, T. Nakayama and K. Mori, Agric. Biol. Chem., 43 (1979) 1571-1575.
24. MM. Midland and N.H. Nguyen, J. Org. Chem., 46 (1981) 4107-4108.
25. R. Baker and V.B. Rao, J. Chem. Soc. Perkin Trans I, (1982) 69-71.
26. Y. Nishida, M. Konno, H. Hori, H. Ohrui and H. Meguro, Agric. Biol. Chem., 51 (1987) 635-640.
27. H. Nemoto, H. Ishibashi, M. Mori, S. Fujita and K. Fukumoto, J. Chem. Soc. Perkin Trans I, (1990) 2835-2840.
28. S. Ramaswamy and A.C. Oehlschlager, Tetrahedron, 47 (1991) 1112-1114.
29. T. Ebata, H. Kqwakami, K. Koseki, K. Matsumoto and H. Matsushita, Biosci. Biotechnol. Biochem., 56 (1992) 818-819.
30. K. Sato, T. Nakayama and K. Mori. Agric. Biol. Chem., 43 (1979) 1571-1575.
31. T. Sugai, S. Ohsawa, H. Yamada and T. Ohta, Synthesis, (1991) 1112-1114.
32. C. Chen, Y. Fujimoto, G. Girdankas and C.J. Sih, J. Am. Chem. Soc., 104 (1982) 7294-7299.
33. E. Fukusaki, S. Senda, Y. Nakazono and T. Omata. Tetrahedron, 47 (1991) 6223-6230.
34. D. Bianch, P. Cesti and E. Battistel, J. Org. Chem., 53 (1988) 5531-5534.
35. C. Chen and C.J. Sih, Angew. Chem. Int. Ed. Engl., 28 (1989) 695-707.
36. K. Nakamura, M. Kinoshita and O.A., Tetrahedron, 51 (1995).
37. A. Bosetti, D. Bianchi, P. Cesti and P. Golini, Biocatalysis, 9 (1994) 71-77.
38. A. Makita, T. Nihira and Y. Yamada, Tetrahedron Lett.. 28 (1987) 805-808.
39. A.L. Gutman, K. Zuobi and T. Bravdo, J. Org. Chem., 55 (1990) 3546-3552.
40. T. Sugai, O. Katoh and H. Ohta, Tetrahedron, 51 (1995) 11987-119998.
41. B. Henkel, A. Kunath and H. Schick, Liebigs Ann. Chem., (1995) 921-923.
42. S.K. Taylor, R.F. Arkinson, F. Richard, E.P. Almli, M.D. Carr and H. Van. Tetrahedron Asymmetry, 6 (1995) 157-164.
43. M. Lobell and M.P. Schneider, Tetrahedron Asymmetry, 4 (1993) 1027-1030.
44. E. Fukusaki, M. Konno, S. Senda and T. Omata, Jpn. Kokai Tokkyo Koho, (1990) JP 90-305719.
45. B.S. Leal, Jpn. Kokai Tokkyo Koho, (1991) JP 91-245990.
46. K. Koseki, H. Kawakami, T. Ebata, H. Matsushita and M. Ono, Jpn. Kokai Tokkyo Koho, (1991) JP 91-77376.
47. E. Fukusaki, S. Senda, Y. Nakazono and T. Omata, Biosci. Biotech. Biochem., 56 (1992) 1160-1161.
48. S. Iwaki, S. Maruo, T. Saito, M. Yamada and K. Katagiri, J. Am. Chem. Soc., 96 (1974) 7842-7844.
49. K. Mori, T. Takigawa and M.M., Tetrahedoron Lett., (1976) 3953-3956.
50. D.G. Farnum, T. Veysoglu, A.M. Carde, B. Duhl-Emswiler, T.A. Pancoast, T.J. Reitz and R.T. Carde. Tetrahedron Lett., (1977) 4009-4012.
51. W.H. Pirkle and P.L. Rinaldi, J. Org. Chem., 44 (1979) 1025-1028.
52. K. Okada, K. Mori and Hirai, Agric. Biol. Chem., 41 (1977) 2485-2486.
53. D.G. Farnum, T. Veysoglu, A.M. Garde, B. Duhl-Emswier, P. Barbara, A. Taylor, T.J. Reitz and R.T. Garde, Tetrahedron Lett., (1977) 4009-4012.
54. K. Mori and T. Ebata, Tetrahedron Lett., 22 (1981) 4281-4282.
55. J.H. Markgraf, S.I. Lusskin, E.C. McDonald and B.D. Volpp, J. Chem. Ecol., 9 (1983) 211-218.
56. H.C. Brown and D. Basavaiah, Synthesis, (1983) 283-284.
57. K.K. Wang and K.H. Chu, J. Org. Chem., 49 (1984) 5175-5178.
58. O.J. Achmatowicz and A. Sadownik, J. Carbohydr. Chem., 4 (1985) 435-440.
59. V.B. Jigajinni and R.H. Wightman, Carbohydr. Res., 147 (1986) 145-148.
60. K. Mori and T. Ebata, Tetrahedron, 42 (1986) 3471-3478.
61. S. Pilul, M. Kozlowska and J. Jurczak, Tetrahedron Lett., 28 (1987) 2627-2628.
62. S. Tsuboi, H. furutani, A. Takeda, K. Kawazoe and S. Sato, Bull. Chem. Soc. Jpn, 60 (1987) 2475-2479.
63. D. Bianch, W. Cabri, P. Cesti, F. Flancalanci and F. Rama, Tetrahedron Lett., 29 (1988) 2455-2358.
64. T. Sato, T. Itoh and T. Fujisawa, Tetrahedron Lett., 28 (1987) 5677-5680.
65. T. Kametani, M. Tsubuki and T. Honda, Chem. Pharm. Bull., 36 (1988) 3706-3709.
66. S. Marczak, M. Masnyk and J. Wicha, Liebigs Ann. Chem., (1990) 345-347.
67. T. Kametani, M. Tsubuki, Y. Tatsuzaki and T. Honda, J. Chem. Soc. Perkin Trans I, (1990) 639-646.
68. S.K. Kang, Y.S. Kim, J.S. Lim. K.S. Kim and S.G. Kim, Tetrahedron Lett., 32 (1991) 353-366.
69. J.L. Brevet and K. Mori, Synthesis, (1992) 1007-1012.
70. E. Keinan, S.C. Sinha, A. Sinha-Bagchi, Z.M. Wang, X.L. Zhang and K.B. Sharpless, Tetrahedron Lett., 33 (1992) 6411-6414.
71. S.Y. Ko, Tetrahedron Lett., 35 (1994) 3601-3604.
72. A. Sinha-Bagchi, S.C. Sinha and E. Keinan, Tetrahedron Asymmetry, 6 (1995) 2889-2892.
73. K. Mori and T. Ebata, Tetrahedron, 42 (1986) 3471-3478.
74. E. Fukusaki, S. Senda, Y. Nakazono, H. Yuasa and T. Omata, J. Ferment. Biotech., 73 (1992) 280-283.
75. C. Berger, C.G. Rabiller, K. Koningsberger, K. Faber and H. Griengl, Tetrahedron Asymmetry, 1 (1990) 541-546.
76. F. Theil, H. Schick, G. Winter and G. Reck, Tetrahedron, 47 (1991) 7569-7582.
77. L.K.P. Lam, R.A.H. Hui and J.B. Jones, J. Org. Chem., 51 (1986) 2047-2050.
78. E. Fukusaki, S. Senda, Y. Nakazono, H. Yuasa and T. Omata, J. Ferment. Biotech., 73 (1992) 284-286.
79. P. Besse and P. Vescheambre, Tetrahedron, 50 (1994) 8885-8927.
80. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune and K.B. Sharpless, J. Am. Chem. Soc., 109 (1987) 5765-5780.
81. B.B. Kine and R.W. Novak, Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 1, 1978, pp. 386-480.
82. T. Matunaga and S. Kono, Jpn. Kokai Tokkyo Koho, (1993).
83. H. Hasebe, K. Takeuchi and H. Takatsu, Jpn. Kokai Tokkyo Koho, (1993) JP93-129008.
84. U. Behrens and H.-Z. Kizerow, Polym. Adv. Technol., 5 (1994) 433-437.
85. T. Budtova and P. Navard, Macromolecules, 29 (1996) 3931-3936.
86. S. Aranganathan and J.C.T. Kwak, Langmuir, 12 (1996) 1381-1390.
87. A. Matsuda, J. Sato, H. Yasunaga and Y. Osada, Macromolecules, 27 (1994) 7695-7698.
88. M. Bryjak, Angew. Makromol. Chem., 215 (1994) 129-138.
89. J.W. Nemec and W. Bauer, Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 1, 1978, pp. 330-354.
90. E. Fukusaki, S. Senda, Y. Nakazono, H. Yuasa and T. Omata, Bioorg. Med. Chem. Lett., 2 (1992) 411-414.
91. T. Kinoshita, H. Akemi, S. Otsuka and Y. Hosaka, Jpn. Kokai Tokkyo Koho, (1990) JP 90-2767998.
92. A. Yamanaka, S. Otsuka, Y. Hosaka, Eur. Pat. Appl. (1991) EP 91-105933.
93. H. Onishi and T. Yatagai, Jpn. Kokai Tokkyo Koho (1988) JP 88-101143.
94. A.L. Margolin, P.A. Fitzpatrick, P.L. Dubin and A.M. Klibanov, J. Am. Chem. Soc., 113 (1991) 4693-4694.
95. I. Ikeda, J. Tanaka and K. Suzuki, Tetrahedron Lett., 32 (1991) 6865-6866.