Lipases: Interfacial enzymes with attractive applications

Angewandte Chemie - International Edition

Volumn 37, Issue 12, 1998, Pages 1608-1633

  Schmid, Rolf D ^a   Verger, Robert ^b  

^a UNIVERSITY OF STUTTGART   (Germany)

^b Ctr de Biochim et de Biol Molec   (France)

Author keywords

Acylations; Enzyme catalysis; Industrial chemistry; Lipases; Metabolism

Indexed keywords

ACYLATION; BIOCATALYST; CATALYST; DEACYLATION; DIGESTIVE SYSTEM; ENANTIOSELECTIVITY; ENZYME INHIBITOR; GENETIC ENGINEERING; ORGANIC SOLVENT; TRIACYLGLYCEROL; TRIACYLGLYCEROL LIPASE;

EID: 0032479388     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980703)37:12<1608::aid-anie1608>3.0.co;2-v     Document Type: Review

References (207)

1. Enzyme Nomenclature (Ed.: International Union of Biochemistry and Molecular Biology), Academic Press, New York, 1992.
2. P. Wooley, S. B. Petersen, Lipases: Their Structure, Biochemistry and Application, Cambridge University Press, Cambridge, 1994.
3. F. D. Gunstone, J. L. Harwood, F. B. Padley, The Lipid Handbook, Chapman & Hall, London, 1995.
4. Lipases: Structure, Mechanism and Genetic Engineering, GBF Monographs, Vol. 16 (Eds.: L. Alberghina, R. D. Schmid, R. Verger), VCH, Weinheim, 1991.
5. H. Brockerhoff, R. G. Jensen, Lipolytic Enzymes, Academic Press, New York, 1974.
6. B. Borgström, H. L. Brockman, Lipases, Elsevier, Amsterdam, 1984.
7. M. Waite in The Phospholipases, Vol. 5 (Ed.: D. J. Hanahn), Plenum, New York, 1987.
8. Phospholipases, Methods Enzymology, Vol. 197 (Ed.: E, A. Dennis), Academic Press, New York, 1991.
9. Engineering of/with Lipases (Ed.: F. X. Malcata), Kluwer, London, 1996.
10. J. Mol. Catal. B 1997, 3 (special issue devoted to "Microbial Lipases in the Biocatalysis").
11. B. Rubin. Structural Biology 1994, 1, 568-572.
12. P. E. Sonnet, J. Am. Oil Chem. Soc. 1988, 65, 900-904.
13. Methods in Enzymology, Vol. 284 (Eds.: B. Rubin, E. A. Dennis), Academic Press, San Diego, 1997.
14. C.-S. Chen, C.J. Sih, Angew. Chem. 1989, 101, 711-724; Angew. Chem. Int. Ed. Engl. 1989, 28, 695-708.
15. C.-S. Chen, C.J. Sih, Angew. Chem. 1989, 101, 711-724; Angew. Chem. Int. Ed. Engl. 1989, 28, 695-708.
16. A. L. Gutman, M. Shapira in Synthetic Applications of Enzymatic Reactions in Organic Solvents, Adv. Biochem. Eng. Biotechnol., Vol. 52 (Ed.: A. Fiechter), Springer, Heidelberg, 1995, pp. 87-128.
17. K. E. Jaeger, S. Ransac, B. W. Dijkstra, C. Colson, M. van Heuvel, O. Misset, FEMS Microbiol. Rev. 1994, 15, 29-63.
18. E. J. Gilbert, Enzyme Microb. Technol. 1993, 15, 634-645.
19. S. Wohlfahrt, K. E. Jaeger, BioEngineering 1993, 9, 39-46.
20. A. H. C. Huang in ref. [6], pp. 419-442.
21. K. D. Mukherjee, M. J. Hills in ref. [2], pp. 49-76.
22. F. Carrière, Y. Gargouri, H. Moreau, S. Ransac, E. Rogalska, R. Verger in ref. [2], pp. 181-205.
23. F. Carrière, S. Bezzine, R. Verger in ref. [10], pp. 55-64.
24. E. Boel, T. Christensen, H. Woldike (Novo Nordisk AS), US-A 5536661, 1996 [Chem. Abstr. 1996, 125, 160364]
25. . [24] M. M. Soumanou, U. T. Bornscheuer, U. Menge, R. D. Schmid, J. Am. Oil Chem. Soc. 1997, 74, 427-433.
26. H. K. Weber, H. Stecher, K. Faber in Preparative Biotransformations: Some Properties Of Commercially Available Crude Lipase Preparations (Ed.: S. M. Rakels), Wiley, New York, 1995.
27. M. R. Aires-Barros, M. A. Taipa, J. M. S. Cabral in Isolation And Purification Of Lipases (Eds.: P. Wooley, S. B. Petersen), Cambridge University Press, Cambridge, 1994, pp. 243-270.
28. S. Ransac, F. Carrière, E. Rogalska, R. Verger, F. Marguet, G. Buono, E. P. Melo, J. M. S. Cabrai, M.-P. E. Egloff, H. van Tilbeurgh, C. Cambillau in The Kinetics, Specificities And Structural Features Of Lipases, Nato ASI Series, Vol. H 96 (Ed.: J. A. F. Op den Kamp), Springer, Berlin, 1996, pp. 265-304.
29. K. Isobe, K. Nokihara, S. Yamaguchi, T. Mase, R. D. Schmid, Eur. J. Biochem. 1992, 203, 233-237.
30. R. Verger, Trends Biotechnol. 1997, 15, 32-38.
31. R. Verger, TIBTECH 1997, 15, 32-38.
32. J. G. T. Kierkels, L. F. W. Vlengels, E. T. F. Gelade, D. P. Vermeulen, J. Kamphuis, C. Wandrey, W. J. J. van den Tweel, Enzyme Microbiol. Technol. 1994, 16, 513-521.
33. M. M. Momsen, M. Dahim, H. L. Brockman, Biochemistry 1997, 36, 10073-10081.
34. S. Ransac, M. G. Ivanova, R. Verger, I. Panaiotov in Methods in Enzymology, Vol. 286 (Eds.: B. Rubin, E. A. Dennis), Academic Press, San Diego, 1997.
35. G. Piéroni, Y. Gargouri, L. Sarda, R. Verger, Adv. Colloid Interface Sci. 1990, 32, 341-378
36. L. de la Fournière, M. G. Ivanova, J. P. Blond, F. Carrière, R. Verger, Colloids Surf. B 1994, 2, 585-593.
37. W. E. Momsen, M. M. Momsen, H. L. Brockman, Biochemistry 1995. 34, 7271-7281.
38. W. Nitsch, R. Maksymiw, H. Erdmann, J. Colloid Interface Sci. 1991, 141, 322-328.
39. L. Sarda, P. Desnuelle, Biochim. Biophys. Acta 1958, 30, 513-521.
40. F. K. Winkler, A. D'Arcy, W. Hunziker, Nature 1990, 343, 771-774.
41. L. Brady, A. M. Brzozowski, Z. S. Derewenda, E. Dodson, G. Dodson, S. Tolley, J. P. Turkenburg, L. Christiansen, B. Huge-Jensen, L. Norskov, L. Thim, U. Menge, Nature 1990, 343, 767-770.
42. A. M. Brzozowski, U. Derewenda, Z. S. Derewenda, G. G. Dodson, D. M. Lawson, J. P. Turkenburg, F. Bjorkling, B. Huge-Jensen, S. A. Patkar, L. Thim, Nature 1991, 351, 491-494.
43. B. Nieuwenhuis in The CEC Bridge Lipase Project (Eds.: L. Alberghina, R. D. Schmid, R. Verger), VCH, Weinheim, 1990, pp. 3-6.
44. M. E. M. Noble, A. Cleasby, L. N. Johnson, L. G. J. Frenken, M. R. Egmond, FEBS Lett. 1993, 331, 123-128.
45. J. Uppenberg, M. T. Patkar, S. Hansen, A. Jones, Structure 1994, 2, 293.
46. H. van Tilbeurgh, M.-P. Egloff, C Martinez, N. Rugani, R. Verger, C. Cambillau, Nature 1993, 362, 814-819.
47. K. Thirstrup, R. Verger, F. Carriére, Biochemistry 1994, 33, 2748-2756.
48. A. Hjorth, F. Carriére, C. Cudrey, H. Wöldike, E. Boel, D. M. Lawson, F. Ferrato, C. Cambillau, G. G. Dodson, L. Thim, R. Verger, Biochemistry 1993, 32, 4702-4707.
49. P. Grochulski, Y. Li, J. D. Schrag, F. Bouthillier, P. Smith, D. Harrison, B. Rubin, M. Cygler, J. Biol. Chem. 1993, 268, 12843-12847.
50. J. D. Schrag, M. Cygler, J. Mol. Biol. 1993, 230, 575.
51. U. Derewenda, L. Swenson, R. Green, Y. Wei, G. G. Dodson, S. Yamaguchi, M. J. Haas, Z. S. Derewenda, Nat. Struct. Biol. 1994, 1, 36-47.
52. C. Martinez, P. de Geuss, M. Lauwereys, G. Matthyssens, C. Cambilleau, Nature 1992, 356, 615-618.
53. J. D. Schrag, Y. Li, M. Cygler, D. Lang, T. Burgdorf, H. J. Hecht, R. D. Schmid, L. C. Strickland, S. B. Larson, J. Day, A. Mc Pherson, Structure 1997, 5, 187-202.
54. D. L. Ollis, E. Cheah, M. Cygler, B. Dijkstra, F. Frolow, S. Franken, M. Harel, S. J. Remington, I. Silman, Protein Eng. 1992, 5, 197-211.
55. U. Derewenda, Z. S. Derewenda, Biochem. Cell. Biol. 1991, 69, 842-851.
56. Z. S. Derewenda, A. M. Sharp, TIBS 1993, 18, 20-25.
57. F. Carriére, J. A. Barrowan, R. Verger, R. Laugier, Gastroenterology 1993, 105, 876-888.
58. G. Scheele, H. Kern in The Exorcine Pancreas, Molecular and Cellular Basis of Digestion (Ed.: P. Desnuelle), Elsevier, Amsterdam, 1986, pp. 173-192.
59. Q. Lüthi-Peng, F. K. Winkler, Eur. J. Biochem. 1992, 205, 383-390.
60. M. P. Egloff, F. Buono, R. Marguet, R. Verger, C. Cambillau, H. van Tilbeurgh, Biochemistry 1995, 34, 2751-2762.
61. Encylopaedia of Chemical Technology (Eds.: R. E. Kirk, D. F. Othmer), Wiley, New York, 1978.
62. W. Connstein, E. Hoyer, H. Wartenberg, Chem. Ber. 1902, 34, 3988-4006.
63. N. O. V. Sonntag in Baileys Industrial Oil and Fat Products (Ed.: D. Swern), Wiley, New York, 1982, pp. 97-111.
64. R. Hashizume, Y. Tanaka, T. Funada (Nippon Oil and Fats Co.), JP-A 03019693 A2, 1991 [Chem. Abstr. 1991, 115, 90690].
65. H. Moore (Unilever PLC), GB-B 2185990 A1, 1987 [Chem. Abstr. 1987, 107, 174780].
66. P. M. J. Holemans, R. Schijf, K. P. A. M. van Putte, T. de Mans (Unilever N.V.; Unilever PLC), EP-B 209176 A1, 1987 [Chem. Abstr. 1987, 106, 118502].
67. S. Bloomer, P. Adlercreutz, B. Mattiasson, J. Am. Oil Chem. Soc. 1990, 67, 519-524.
68. A. R. Macrae, J. Am. Oil Chem. Soc. 1983, 60, 291-294.
69. M. H. Coleman. A. R. Macrae (Unilever N.V.), DE-B 2705 608, 1977 [Chem. Abstr. 1977, 87, 166366].
70. T. Matsuo, N. Sawamura, Y. Hashimoto, W. Hashida (Fuji Oil Co.), EP-B 0035883 A2, 1982 [Chem. Abstr. 1982, 96, 4958y].
71. C. C. Akoh, INFORM 1995, 6, 1055-1061.
72. B. Ö. Gudmundsson, Ö. Almarsson, G. G. Haraldsson, Tetrahedron Lett. 1993, 34, 5791-5794.
73. H. Baumann, M. Bühler, H. Fochem, F. Hirsinger, H. Zoebelein, J. Falbe, Angew. Chem. 1988, 100, 41-62; Angew. Chem. Int. Ed. Engl. 1988, 27, 41-62.
74. H. Baumann, M. Bühler, H. Fochem, F. Hirsinger, H. Zoebelein, J. Falbe, Angew. Chem. 1988, 100, 41-62; Angew. Chem. Int. Ed. Engl. 1988, 27, 41-62.
75. N. O. V. Sonntag, J. Am. Oil Chem. Soc. 1982, 59, 795A-802A.
76. U. T. Bornscheuer, Enzyme Microb. Technol. 1995, 17, 578-586.
77. S. Moore, P. Quinlan, INFORM 1993, 4, 579-583.
78. V. Partali, L. Kvittingen, H.-R. Sliwka, T. Anthonson, Angew. Chem. 1996, 108, 342-344; Angew. Chem. Int. Ed. Engl. 1996, 35, 329-330.
79. V. Partali, L. Kvittingen, H.-R. Sliwka, T. Anthonson, Angew. Chem. 1996, 108, 342-344; Angew. Chem. Int. Ed. Engl. 1996, 35, 329-330.
80. A. M. Wolff, M. S. Showell in Enzymes in Detergency (Eds.: J. H. Van Ee, O. Misset, E. J. Baas), Marcel Dekker, New York, 1997, pp. 93-106
81. O. Misset in ref. [77], pp. 107-132.
82. E. Gormsen, M. Lykke, C. F. Jensen, Rev. Quim. Text. 1994, 120, 78-81.
83. B. Kottwitz, H. Upadek, G. Carrer, Chim. Oggi 1994, 12, 21-24.
84. O. Kirk, M. W. Christensen, T. Damhus, S. E. Godtfredsen, Biocatalysis 1994, 11, 65-77.
85. H. Andree, R. W. Müller, R. D. Schmid, J. Appl. Biochem. 1980, 2, 218-229.
86. Y. Fujita, H. Awaji, M. Matsukura, K. Hata, H. Shimoto, M. Sharyo, H. Skaguchi, K. Gibson, Tappi J. 1992, 75, 117-122.
87. E. N. Vulfson in ref. [2], pp. 271-286.
88. K. Faber, Biotransformations in Organic Chemistry, Springer, Heidelberg, 1995.
89. K. Drauz, H. Waldmann, Enzyme Catalysis in Organic Synthesis, VCH, Weinheim, 1995.
90. R. A. Sheldon, Chirotechnology: Industrial Synthesis of Optically Active Compounds, Marcel Dekker, New York, 1993.
91. R. Kazlauskas, U. T. Bornscheuer in Biotechnology, Vol. 8a (Eds.: H. J. Rehm, G. Reed, A. Pühler, P. J. W. Stadler, D. R. Kelly), VCH, Weinheim, 1998, pp. 37-191.
92. K. Faber, Pure Appl. Chem. 1997, 69, 1613-1632.
93. A. M. P. Koskinen, A. M. Klibanov, Enzymatic Reactions in Organic Media, Blackie, London, 1996.
94. H. P. Kaufmann, M. C. Keller, Fette Seifen 1937, 44, 105-107.
95. H. P. Kaufmann, M. C. Keller, Fette Seifen 1937, 44, 42-47.
96. J. S. Dordick, Biotechnol. Prog. 1992, 8, 259-267.
97. M. N. Gupta, Eur. J. Biochem. 1992, 203, 25-32.
98. E. Santaniello, P. Ferraboschi, P. Grisenti, Enzyme Microb. Technol. 1993, 75, 367-381.
99. F. Effenberger, B. Gutterer, T. Ziegler, E. Eckhardt, R. Aichholz, Liebigs Ann. Chem. 1991, 47-54.
100. M. Schneider, E. H. Reimerdes, Forum Mikrobiol. 1987, 65-71.
101. F. Theil, Chem. Rev. 1995, 95, 2203-2227.
102. K. Mori, Synlett 1995, 1097-1109.
103. C. H. Wong, J. M. Fang, Synlett 1994, 393-402.
104. A. L. Margolin, Enzyme Microb. Technol. 1993, 15, 266-279.
105. C. Froessl, M. Lorenz, W. Boland, Synthesis 1991, 1049-1072.
106. G. M. Whitesides, C.-H. Wong, Angew. Chem. 1985, 97, 617-620; Angew. Chem. Int. Ed. Engl. 1985, 24, 617-620.
107. G. M. Whitesides, C.-H. Wong, Angew. Chem. 1985, 97, 617-620; Angew. Chem. Int. Ed. Engl. 1985, 24, 617-620.
108. H. P. Schär, X. F. Busquets, O. Ghisalba, G. M. R. Tombo, Tetrahedron Lett. 1986, 27, 5707-5710.
109. E. L. A. Mac Farlane, S. N. Roberts, N. J. Turner, J. Chem. Soc. Chem. Comm. 1990, 569-571.
110. C. S. Chen, Y. Fujimoto, C. J. Sih, J. Am. Chem. Soc. 1982, 104, 7294-7299.
111. C. S. Chen, S. H. Wu, G. Girdaukas. C. J. Sih, J. Am. Chem. Soc. 1987, 109, 2812-2817.
112. M. Castaing-Degueil, B. de Jeso, S. Drouillard, B. Maillard, Tetrahedron Lett. 1987, 28, 953-954.
113. Y. F. Wang, J. J. Lalonde, M. Momongan, D. E. Bergbreiter, C. H. Wong, J. Am. Chem. Soc. 1988, 110, 7200-7205.
114. H. M. R. Hoffmann, U. T. Bornscheuer, T. F. J. Lampe, Tetrahedron: Asymmetry 1996, 7, 2889-2900.
115. R. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport, L. A. Cuccia, J. Org. Chem. 1991, 56, 2656-2665.
116. P. Grochulski, F. Bouthillier, R. Kazlauskas, A.N. Serreqi, J. D. Schrag, E. Ziomek, M. Cygler, Biochemistry 1994, 33, 3494-3500.
117. R. Bovara, G. Carrea, L. Ferrara, S. Riva, Tetrahedron: Asymmetry 1991, 2, 931-938.
118. R. Chenevert, R. Pouliot, P. Bureau, Bioorg. Med. Chem. Lett. 1994, 4, 2941-2944.
119. S. J. Phythian, A. J. Reason, S. M. Roberts, N. B. Bashir, J. Chem. Soc. Perkin Trans. 1 1995, 2203-2222.
120. C. H. Wong, Pure Appl. Chem. 1995, 67, 1609-1616.
121. J. Chopineau, A. P. G. Kieboom, A.M. Klibanov, S. Riva, J. Am. Chem. Soc. 1988, 110, 584-589.
122. M. Therisod, A. M. Klibanov, J. Am. Chem. Soc 1986, 108, 5638-5640.
123. R. Pulido, V. Gotor, J. Chem. Soc. Perkin Trans. 1 1991, 491-492.
124. C. Scheckermann, A. Schlotterbeck, M. Schmid, Enzyme Microb. Technol 1995, 17, 157-162.
125. A. M. Klibanov, M. Therisod, J. Am. Chem. Soc. 1987, 109, 3977-3981.
126. S. Riva, F. Secundo, L. Zucchelli, F. Nicotra, Tetrahedron Lett. 1989, 30, 1703-1704.
127. R. Pulido, F. O. Lòpez, V. Gotor, J. Chem. Soc. Perkin Trans. 1 1992, 1, 2981-2988.
128. A. E. M. Janssen, C. Klabbers, M. C. R. Franssen, K. van't Reit, Enzym Microb. Technol. 1991, 13, 565-571.
129. L. Cao, A. Fischer, U. T. Bornscheuer, R. D. Schmid, Biocatal. Biotrans. 1997, 14, 269-283.
130. B. Morgan, A. C. Oehlschlager, T. M. Stokes, J. Org. Chem. 1992, 57, 3231-3236.
131. H. Edlund, P. Berglund, M. Jensen, E. Hedenstroem, H.-E. Hoegberg, Acta Chim. Scand. 1996, 50, 666-671.
132. A. L. Margolin, Tetrahedron Lett. 1990, 31, 6797.
133. L. Salazar, C. J. Sih, Tetrahedron: Asymmetry 1995, 6, 2917-2920.
134. M. M. Enzelberger, U. T. Bornscheuer, I. Gattfield, R. D. Schmid, J. Biotechnol. 1997, 56, 129-134.
135. A. L. Gutman, T. Bravdo, J. Org. Chem. 1989, 54, 4263-4265.
136. F. Theil, H. Schick, G. Winter, G. Reck, Tetrahedron 1991, 47, 7569-7582.
137. C. R. Johnson, A. Golebiowski, D. H. Steensma, J. Am. Chem. Soc. 1992, 114, 9414-9418.
138. V. Sunjic, Croat. Chem. Acta 1994, 67, 365-392.
139. C. Andreu, J. A. Macro, G. Asensio, J. Chem. Soc. Perkin Trans. 1 1990, 3209-3210.
140. S. Takano, M. Moriaya, Y. Higashi, K. Ogasawara, J. Chem. Soc. Chem. Comm. 1993, 177-178.
141. S. Puertas, R. Brieva, F. Rebolledo, V. Gotor, Tetrahedron 1993, 49, 4007-4014.
142. R. Brieva, F. Rebolledo, V. Gotor, J. Chem. Soc. Chem. Commun. 1990, 1386-1387.
143. A. L. Gutman, E. Meyer, X. Yue, C. Abell, Tetrahedron Lett. 1992, 33, 3943-3946.
144. M. C. de Zoete, F. van Rantwijk, R. A. Sheldon (Delft University of Technology), WO-A 9507359 A1, 1995 [Chem. Abstr. 1995, 122, 313055].
145. M. C. de Zoete, A. C. Kock-van Dalen, F. van Rantwijk, R. A. Sheldon, J. Chem. Soc. Chem. Commun. 1993, 1831-1832.
146. M. C. de Zoete, A. C. Kock-van Dalen, F. van Rantwijk, R. A. Sheldon, Biocatalysis 1994, 10, 307-316.
147. M. C. de Zoete, F. van Rantwijk, L. Maat, R. A. Sheldon, Recl. Trav. Chim. Pays-Bas 1993, 112, 462-463.
148. N. Baba, M. Mimura, J. Hiratake, K. Uchida, J. Oda, Agric. Biol. Chem. 1988, 52, 2685-2687.
149. E. Guibe-Jampel, M. Bassir, Tetrahedron Lett. 1994, 35 , 421-422.
150. J. Z. Crich, R. Brieva, P. Marquart, R. L. Gu, S. Flemming, C. J. Sih, J. Org. Chem. 1993, 58, 3252-3258.
151. M. Bucciarelli, A. Forni, I. Moretti, F. Prati, G. Torre, Tetrahedron: Asymmetry 1993, 4, 903-906.
152. P. Cesti, D. Bianchi, J. Org. Chem. 1990, 55, 5657-5659.
153. J. M. Chong, K. M. Mar. Tetrahedron Lett. 1991, 32, 5683-5686.
154. S. Kurita, S. Ueji, T. Yamada, S. Kuwata, T. Miyazawa, Biotechnol. Lett. 1992, 14, 941-946.
155. G. Nicolosi, R. Morrone, A. Patti, M. Piatelli, Tetrahedron: Asymmetry 1992, 3, 753-758.
156. K. Nakamura, K. Ishihara, A. Ohno, M. Uemura, H. Nishimura, Y. Hayashi, Tetrahedron Lett. 1990, 31, 3603-3604.
157. L. A. Hulshof, J. H. Roskam (Stamicarbon B.V.). EP-B 343714 A1, 1989 [Chem. Abstr. 1990, 113, 76603].
158. K. Wünsche, U. Schwaneberg, U. T. Bornscheuer, H. H. Meyer, Tetrahedron: Asymmetry 1996, 7, 2017-2022.
159. M. Kloosterman, V. H. M. Elferink, J. van Iersel, J. H. Roskam, E. M. Meijer, L. A. Hulshof, R. A. Sheldon, TIBTECH 1988, 6, 251-256.
160. S. Mitsuda, S. Nabeshima, H. Hirohara, Appl. Microbiol. Biotechnol. 1989, 31, 334-337.
161. C. S. Chen, S. Hsiung, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc. 1987. 109, 2812-2817.
162. D. Bianchi, T. Sugai, H. Ohta, Agric. Biol. Chem. 1991, 55, 293-294.
163. P. Cesti, E. Battistel, D. Bianchi, J. Org. Chem. 1988, 53, 5531-5534.
164. S. Brandt. R. F. Rossi, D. R. Dodds, J. L. Lopez (Sepracor Inc.), WO-A 9004643 A1, 1990 [Chem. Abstr. 1990, 113, 76620].
165. T. Shibatani, Yukagaku 1995, 44, 862-868 [Chem. Abstr. 1995, 123, 312256].
166. T. Shibatani, Yukagaku 1995, 44, 862-868 [Chem. Abstr. 1995, 123, 312256].
167. H. R. Sonawane, N. S. Bellur, J. R. Ahuya, D. G. Kulkarni, Tetrahedron: Asymmetry 1992, 3, 163-192.
168. D. Bianchi, W. Cabri, P. Cesti, F. Francalanci, M. Ricci, J. Org. Chem. 1988, 53, 104-107.
169. J. M. Moreno, J. V. Sinisterra, J. Mol. Catal. A 1995, 98, 171-184.
170. S. Mitsuda, S. Nabeshima, H. Hirhora, Appl. Microbiol. Biotechnol. 1989, 31, 334-337.
171. F. Balkenhohl, K. Ditrich, B. Hauer, W. Ladner, J. Prakt. Chem. 1997, 339, 381-384.
172. D. L. Hughes, J. J. Bergan, J. S. Amato, P. J. Reider, E. J. J. Grabowski, J. Org. Chem. 1989, 54, 1787-1788.
173. S. Hamaguchi, M. Asada, J. Hasegawa, K. Watanabe, Agric. Biol. Chem. 1985, 49, 1661-1667.
174. R. L. Rizek, B. Friend, L. Page, J. Am. Oil Chem. Soc. 1974, 51, 244-250.
175. M. Hamosh, D. Ganot, P. Hamosh, J. Biol. Chem. 1979, 254, 12121 -12125.
176. M. Aoubala, I. Douchet, R. Laugier, M. Hirn, R. Verger, A. de Caro, Biochim. Biophys. Acta 1993, 1169, 183-189.
177. C. Tiruppathi, K. A. Balasubramanian, Biochim. Biophys. Acta 1982, 712,692-697.
178. J. de Caro, F. Ferrato, R. Verger, A. de Caro, Biochim. Biophys. Acta 1995, 1252, 321-329.
179. H. Moreau, Y. Gargouri, D. Lecat, R. Verger, J. L. Junien, Biochim. Biophys. Acta 1988, 960, 286-293.
180. F. Carrieáre, H. Moreau, V. Raphel, R. Laugier, C. Benicourt, J. L. Junien, R. Verger, Eur. J. Biochem. 1991, 202, 75-83.
181. C. K. Abrams, M. Hamosh, V. S. Hubbard, S. K. Datta, P. Hamos, J. Clin. Invest. 1984, 73, 374-382.
182. Y. Gargouri, H. Moreau, R. Verger, Biochim. Biophys. Acta 1989, 1006, 255-271.
183. A. Suzuki, A. Mizumoto, M. J. Sarr, E. P. Dimagno, Gastroenterology 1997, 112, 2048-2055.
184. C. Wicker-Planquart, S. Canaan, M. Riviére, L. Dupuis, R. Verger, Protein Eng. 1996, 9, 1225-1232.
185. F. Carriére, H. Moreau, V. Raphel, R. Laugier, C. Bénicourt, J. L. Junien, R. Verger, Eur. J. Biochem. 1991, 202, 75-83.
186. C. Bénicourt, C. Blanchard, F. Carriére, R. Verger, J. L. Junien in Clinical Ecology of Cystic Fibrosis (Eds. : H. Escobar, C. F. S. Baquero), Elsevier, Amsterdam, 1993, pp. 291-295.
187. P. Hadváry, H. Lengsfeld, H. Wolfer, Biochem. J. 1988, 256, 357-361.
188. B. Borgstrom, Biochim. Biophys. Acta 1988, 962, 308.
189. P. Hadváry, W. Sidler, W. Meister, W. Vetter, H. Wolfer, FEBS Lett. 1992, 299, 111-115.
190. C. Cudrey, H. van Tilbeurgh, Y. Gargouri, R. Verger. Biochemistry 1993, 32, 13800-13808.
191. S. Ransac, Y. Gargouri, F. Marguet, G. Buono, C. Beglinger, P. Hildebrand, H. Lengsfeld, P. Hadváry, R. Verger in ref. [33], pp. 190-231.
192. A. Svendsen, I. G. Clausen, S. A. Patkar, E. Gormsen (Novo Nordisk), WO-A 9205249 A1, 1992 [Chem. Abstr. 1993, 118, 35131],
193. A. Svendsen, I. G. Clausen, S. A. Patkar, E. Gormsen (Novo Nordisk), WO-A 9311254 A1, 1993 [Chem. Abstr. 1993, 119, 176669].
194. A. Svendsen, I. G. Clausen, S. A. Patkar, E. Gormsen (Novo Nordisk), WO-A 9425577 A1, 1994 [Chem. Abstr. 1995, 122, 155213].
195. A. M. Batenburg, M. R. Egmond, L. G. J. Frenken, C. T. Verrips (Unilever PLC), EP-B 407225 A1, 1991 [Chem. Abstr. 1991, 115, 25076].
196. M. L. F. Giuseppin, M. T. S. Lopes, R. J. Planta, J. M. A. Verbakel, C. T. Verrips (Unilever PLC), WO-A 9100920 A2, 1991 [Chem. Abstr. 1991, 115, 134185].
197. A. J. Poulose, S. A. Anderson (Clorox Co.), EP-B 375102 A2, 1990 [Chem. Abstr. 1990, 113, 174516].
198. G. L. Gray, S. D. Scott, A. J. Ayrookaran (Genencor Inc.) US-A 5389536 A, 1995 [Chem. Abstr. 1995, 122, 234312].
199. J. M. Van der Laan, H. B. M. Lenting, L. J. S. M. Mulleners, M. M. J. Cox (Gist-Brocades N.V.), WO-A 9425578 A1, 1994 [Chem. Abstr. 1995, 122, 127550x].
200. W. Aehle, G. Gerritse, H. B. M. Lenting (Gist-Brocades B.V.), WO-A 9530744 A2, 1995 [Chem. Abstr. 1996, 124, 110997s].
201. R. D. Joerger, M. J. Haas, Lipids 1994, 29, 377-384.
202. T. Yoneda, Y. Miyota, K. Ohno, J. Sasuga (Showa Denko), WO-A 9514783 A1, 1995 [Chem. Abstr. 1995, 123, 221785].
203. D. J. H. Gaskin, A. H. Bovagnet, N. A. Turner, E. N. Vulfson, Biochem. Soc. Trans. 1997, 25, 158.
204. J. C. Moore, F. H. Arnold, Nature Biotechnol. 1996, 14, 458-467.
205. D. L. Mc Beth, B. Hauer, Appl. Environ. Microbiol. 1996, 62, 3538-3540.
206. Note added in proof (May 13, 1998): Since the completion of the manuscript one year ago, the amount of literature on lipases increased in all areas ranging from basic research to applications. A first example for the directed evolution of a lipase from Pseudomonas aeruginosa PAO1 was described: M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger, Angew. Chem. 1997, 109, 2961-2963; Angew. Chem. Int. Ed. Engl. 1997, 36, 2830-2832.
207. Note added in proof (May 13, 1998): Since the completion of the manuscript one year ago, the amount of literature on lipases increased in all areas ranging from basic research to applications. A first example for the directed evolution of a lipase from Pseudomonas aeruginosa PAO1 was described: M. T. Reetz, A. Zonta, K. Schimossek, K. Liebeton, K.-E. Jaeger, Angew. Chem. 1997, 109, 2961-2963; Angew. Chem. Int. Ed. Engl. 1997, 36, 2830-2832.