Lipase action on some non-triglyceride substrates

Journal of Molecular Catalysis B: Enzymatic

Volumn 22, Issue 5-6, 2003, Pages 279-298

  Vallikivi, Imre ^a   Lille, Ülo ^a   Lookene, Aivar ^b   Metsala, Andrus ^a   Sikk, Peeter ^b   Tõugu, Vello ^b   Vija, Heiki ^b   Villo, Ly ^a   Parve, Omar ^a  

^a TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

^b NATIONAL INSTITUTE OF CHEMICAL PHYSICS AND BIOPHYSICS   (Estonia)

Author keywords

Deoxysugars; Hemiacetal decyclization; Lipase catalyzed reactions; Lipase triggered cascade reactions; Prostanoids

Indexed keywords

CATALYSIS; COMPLEXATION; MOLECULES;

LIPASE;

ENZYMES;

11 ACETYLPROSTAGLANDIN E2; 11 ACETYLPROSTAGLANDIN E2 ALPHA METHYL ESTER; 11 ACETYLPROSTAGLANDIN E2 METHYL ESTER; ACETAL DERIVATIVE; ALDEHYDE; ALKANOIC ACID; CLOPROSTENOL; FLUORIDE; FUNCTIONAL GROUP; HYDROXYALDEHYDE; PHOSPHONIC ACID DERIVATIVE; PROSTAGLANDIN A2; PROSTAGLANDIN E1; PROSTAGLANDIN E2; PROSTANOID; QUERCETIN; TRIACYLGLYCEROL; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; WATER;

ACETYLATION; ACYLATION; BIOCATALYST; BIOENGINEERING; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHIRALITY; CYCLIZATION; DERIVATIZATION; DRUG SCREENING; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME SPECIFICITY; EPOXIDATION; ESTERIFICATION; EXTRACTION; HALOGENATION; HYDROLYSIS; ISOLATION PROCEDURE; ISOMER; KINETICS; LIQUID; METHODOLOGY; MICROWAVE RADIATION; MOLECULAR DYNAMICS; MOLECULAR RECOGNITION; MOLECULE; MONITORING; PH; PROTECTION; REACTION ANALYSIS; REVIEW; RING CLOSING METATHESIS; SCREENING TEST; SEPARATION TECHNIQUE; STEREOCHEMISTRY; SUPERCRITICAL FLUID; TEMPERATURE; ULTRASOUND; VELOCITY;

EID: 0038015676     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1177(03)00043-2     Document Type: Article

References (130)

1. K. Faber, Biotransformations in Organic Chemistry, fourth ed., Springer, Heidelberg, 2000.
2. U.T. Bornscheuer, R.J. Kazlauskas, Hydrolases in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
3. A.M.P. Koskinen, A.M. Klibanov, Enzymatic Reactions in Organic Media, Kluwer Academic Publishers, Dordrecht, 1995.
4. P. Berglund, K. Hult, Biocatalytic synthesis of enantiopure compounds using lipases, in: R.N. Patel (Ed.), Stereoselective Biocatalysis, Marcel Dekker, New York, 2000, Chapter 21, pp. 633-657.
5. S.M. Roberts, N.J. Turner, A.J. Willetts, M.K. Turner, Introduction to Biocatalysis Using Enzymes and Micro-Organisms, Cambridge University Press, Cambridge, 1995.
6. L. Poppe, L. Novak, Selective Biocatalysis, Verlag Chemie, Weinheim, 1992.
7. Schmid R.D., Verger R. Angew. Chem. Int. Ed. 37:1998;1608.
8. Theil F. Chem. Rev. 95:1995;2203.
9. Zaks A., Dodds D.R. DDT. 2:1997;513.
10. Roberts S.M. J. Chem. Soc., Perkin Trans. 1:1998;157.
11. Roberts S.M. J. Chem. Soc., Perkin Trans. 1:1999;1.
12. Loughlin W.A. Bioresource Technol. 74:2000;49.
13. Yahya A.R.M., Anderson W.A., Moo-Young M. Enzyme Microbial Technol. 23:1998;438.
14. Muralidhar R.V., Marchant R., Nigam P. J. Chem. Technol. Biotechnol. 76:2001;3.
15. Gross R.A., Kumar A., Kalra B. Chem. Rev. 101:2001;2097.
16. Klibanov A.M. TIBTECH. 15:1997;97.
17. Verger R. TIBTECH. 15:1997;32.
18. Dodson G., Wlodawer A. TIBS. 23:1998;347.
19. Rozzell J.D. Bioorg. Med. Chem. 7:1999;2253.
20. Holmquist M. Curr. Protein Peptide Sci. 1:2000;209.
21. Kazlauskas R.J. Curr. Opin. Chem. Biol. 4:2000;81.
22. Villo L., Metsala A., Parve O., Pehk T. Tetrahedron Lett. 43:2002;3203.
23. Parve O., Järving I., Martin I., Metsala A., Vallikivi I., Aidnik M., Pehk T., Samel N. Bioorg. Med. Chem. Lett. 9:1999;1853.
24. Baumann M., Hauer B.H., Bornscheuer U.T. Tetrahedron: Asymmetry. 11:2000;4781.
25. Parve O., Vallikivi I., Metsala A., Lille Ü., Tõugu V., Sikk P., Käämbre T., Vija H., Pehk T. Tetrahedron. 53:1997;4889.
26. Kazlauskas R.J., Weissfloch A.N., Rappaport A.T., Cuccia L.A. J. Org. Chem. 56:1991;2656.
27. Borreguero I., Sinisterra J.V., Rumbero A., Hermoso J.A., Martinez-Ripoll M., Alcantara A.R. Tetrahedron. 55:1999;14961.
28. Lemke K., Lemke M., Theil F. J. Org. Chem. 62:1997;6268.
29. Orrenius C., Hæffner F., Rotticci D., Öhrner N., Norin T., Hult K. Biocatal. Biotrans. 16:1998;1.
30. Hæffner F., Norin T., Hult K. Biophys. J. 74:1998;1251.
31. Raza S., Fransson L., Hult K. Protein Sci. 10:2001;329.
32. Tafi A., Van Almsick A., Corelli F., Crusco M., Laumen K.E., Schneider M.P., Botta M. J. Org. Chem. 65:2000;3659.
33. Botta M., Cernia E., Corelli F., Manetti F., Soro S. BBA. 1296:1996;121.
34. Weber H.K., Weber H., Kazlauskas R.J. Tetrahedron: Asymmetry. 10:1999;2635.
35. Brecker L., Ribbons D.W. TIBTECH. 18:2000;197.
36. Berglund P. Biomol. Eng. 18:2001;13.
37. Yang H., Henke E., Bornscheuer U.T. J. Org. Chem. 64:1999;1709.
38. R. Morrone, M. Piatelli, G. Nicolosi, Eur. J. Org. Chem. (2001) 1441.
39. Dumont T., Barth D., Perrut M. J. Supercrit. Fluids. 6:1993;85.
40. Knez Z., Rizner V., Habulin M., Bauman D. J. Am. Oil Chem. Soc. 72:1995;1345.
41. Parve O., Vallikivi I., Lahe L., Metsala A., Lille Ü., Tõugu V., Vija H., Pehk T. Bioorg. Med. Chem. Lett. 7:1997;811.
42. Perrut M. High Pressure Biotechnol. 224:1992;401.
43. Kim K.-W., Song B., Choi M.-Y., Kim M.-J. Org. Lett. 3:2001;1507.
44. Lau R.M., Van Rantwijk F., Seddon K.R., Sheldon R.A. Org. Lett. 2:2000;4189.
45. Theil F. Tetrahedron. 56:2000;2905.
46. Ottosson J., Fransson L., King J.W., Hult K. BBA. 1594:2002;325.
47. Khmelnitsky Y.L., Welch S.H., Clark D.S., Dordick J.S. J. Am. Chem. Soc. 116:1994;2647.
48. T. Okamoto, S. Ueji, Chem. Commun. (1999) 939.
49. Ke T., Klibanov A.M. J. Am. Chem. Soc. 121:1999;3334.
50. Kvittingen L., Sjursnes B., Anthonsen T., Halling P. Tetrahedron. 48:1992;2793.
51. Fojan P., Jonson P.H., Petersen M.T.N., Petersen S.B. Biochimie. 82:2000;1033.
52. Our unpublished results.
53. Ottosson J., Hult K. J. Mol. Catal. B: Enzym. 11:2001;1025.
54. Kvittingen L., Sjursnes B., Halling P., Anthonsen T. Tetrahedron. 48:1992;5259.
55. Lin G., Lin W.Y. Tetrahedron Lett. 39:1998;4333.
56. Carrillo-Munoz J.-R., Bouvet D., Guibe-Jampel E., Loupy A., Petit A. J. Org. Chem. 61:1996;7746.
57. Ponne C.T., Möller A.C., Tijskens L.M.M., Bartels P.V., Meijer M.M.T. J. Agric. Food Chem. 44:1996;2818.
58. Hungerhoff B., Sonnenschein H., Theil F. Angew. Chem. Int. Ed. 40:2001;2492.
59. van den Heuvel M., Cuiper A.D., van der Deen H., Kellogg R.M., Feringa B.L. Tetrahedron Lett. 38:1997;1655.
60. Strauss U.T., Faber K. Tetrahedron: Asymmetry. 10:1999;4079.
61. El Gihani M.T., Williams J.M.J. Curr. Opin. Chem. Biol. 3:1999;11.
62. Azerad R., Buisson D. Curr. Opin. Biotechnol. 11:2000;565.
63. Vänttinen E., Kanerva L.T. Tetrahedron: Asymmetry. 6:1995;1779.
64. Lee D., Choi Y.K., Kim M.-J. Org. Lett. 2:2000;2553.
65. Cipiciani A., Cittadini M., Fringuelli F. Tetrahedron. 54:1998;7883.
66. DeSantis G., Jones J.B. Curr. Opin. Biotechnol. 10:1999;324.
67. Magnusson A., Hult K., Holmquist M. J. Am. Chem. Soc. 123:2001;4354.
68. Manetti F., Mileto D., Corelli F., Soro S., Palocci C., Cernia E., D'Acquarica I., Lotti M., Alberghina L., Botta M. BBA. 1543:2000;146.
69. Kazlauskas R.J., Weber H.K. Curr. Opin. Chem. Biol. 2:1998;121.
70. Svendsen A. BBA. 1543:2000;223.
71. Villeneuve P., Muderhwa J.M., Graille J., Haas M.J. J. Mol. Catal. B: Enzym. 9:2000;113.
72. Cotterill I.C., Macfarlane E.L.A., Roberts S.M. J. Chem. Soc., Perkin Trans. 1:1988;3387.
73. Klempier N., Faber K., Griengl H. Biotech. Lett. 2:1989;685.
74. Klempier N., Geymayer P., Stadler P., Faber K., Griengl H. Tetrahedron: Asymmetry. 1:1990;111.
75. Parve O., Pals A., Kadarpik V., Lille Ü., Sikk P., Lõokene A., Välimäe T. Bioorg. Med. Chem. Lett. 3:1993;357.
76. Carriere F., Withers-Martinez C., van Tilbeurgh H., Roussel A., Cambillau C., Verger R. BBA. 1376:1998;417.
77. Berglund P., Vallikivi I., Fransson L., Dannacher H., Holmquist M., Martinelle M., Björkling F., Parve O., Hult K. Tetrahedron: Asymmetry. 10:1999;4191.
78. J. Spreitz, R. Grobbauer, H. Griengl, K. Faber, Braumschweig (1990) 93.
79. Berger B., Rabiller C.G., Königsberger K., Faber K., Griengl H. Tetrahedron: Asymmetry. 1:1990;541.
80. H. Hönig, P. Seufer-Wasserthal, Synthesis (1990) 1137.
81. Berkowitz D.B., Hartung R.E., Choi S. Tetrahedron: Asymmetry. 10:1999;4513.
82. Ciuffreda P., Casati S., Santaniello E. Tetrahedron. 56:2000;317.
83. Maestro A., Astorga C., Gotor V. Tetrahedron: Asymmetry. 8:1997;3153.
84. Tumlinson J.H., Kleinn M.G., Doolittle R., Latt T.T., Proveaux A.T. Science. 197:1977;789.
85. Parve O., Aidnik M., Lille Ü., Martin I., Vallikivi I., Vares L., Pehk T. Tetrahedron: Asymmetry. 9:1998;885.
86. Aav R., Parve O., Pehk T., Claesson A., Martin I. Tetrahedron: Asymmetry. 10:1999;3033.
87. Caron G., Tseng G.W.-M., Kazlauskas R.J. Tetrahedron: Asymmetry. 5:1994;83.
88. Node M., Inoue T., Araki M., Nakamura D., Nishide K. Tetrahedron: Asymmetry. 9:1998;157.
89. Yang H., Henke E., Bornscheuer U.T. Tetrahedron: Asymmetry. 10:1999;957.
90. Sánchez V.M., Rebolledo F., Gotor V. J. Org. Chem. 64:1999;1464.
91. Majeriæ M., Šunjiæ V. Tetrahedron: Asymmetry. 7:1996;815.
92. Parve O., Pals A., Kadarpik V., Lahe L., Lille Ü., Sikk P., Lõokene A., Välimäe T. Bioorg. Med. Chem. Lett. 3:1993;359.
93. Lopez-Serrano P., Jongejan J.A., van Rantwijk F., Sheldon R.A. Tetrahedron: Asymmetry. 12:2001;219.
94. Mayer S.F., Steinreiber A., Orru R.V.A., Faber K. Tetrahedron: Asymmetry. 12:2001;41.
95. Steinreiber A., Edegger K., Mayer S.F., Faber K. Tetrahedron: Asymmetry. 12:2001;2067.
96. Toone E.J., Jones J.B. Tetrahedron: Asymmetry. 2:1991;207.
97. Högberg H.-E., Lindmark M., Isaksson D., Sjödin K., Franssen M.C.R., Jongejan H., Wijnberg J.B.P.A., de Groot A. Tetrahedron Lett. 41:2000;3193.
98. Parve O., Vallikivi I., Lahe L., Sikk P., Käämbre T., Lille Ü. Proc. Estonian Acad. Sci. Chem. 46:1997;186.
99. R. Chenevert, M. Desjardins, R. Gagnon, Chem. Lett. (1990) 33.
100. Egri G., Fogassi E., Novak L., Poppe L. Tetrahedron: Asymmetry. 8:1997;547.
101. Cordova A., Hult K., Iversen T. Biotechnol. Lett. 19:1997;15.
102. Gridley J.J., Hacking A.J., Osborn H.M.I., Spackman D.G. Tetrahedron. 54:1998;14925.
103. La Ferla B., Lay L., Russo G., Panza L. Tetrahedron: Asymmetry. 11:2000;3647.
104. Bastida A., Fernandez-Lafuente R., Fernandez-Lorente G., Guisan J.M., Pagani G., Terreni M. Bioorg. Med. Chem. Lett. 9:1999;633.
105. Maugard T., Remaud-Simeon M., Petre D., Monsan P. J. Mol. Catal. B: Enzym. 5:1998;13.
106. Otto R.T., Scheib H., Bornscheuer U.T., Pleiss J., Syldatk C., Schmid R.D. J. Mol. Catal. B: Enzym. 8:2000;201.
107. Bousquet M.-P., Willemot R.M., Monsan P., Boures E. Biotecnol. Bioeng. 62:1999;225.
108. Cordova A., Iversen T., Hult K. Macromolecules. 31:1998;1040.
109. Ferrero M., Gotor V. Chem. Rev. 100:2000;4319.
110. Boto A., Hernandez R., Suarez E. Tetrahedron Lett. 42:2001;9167.
111. Rotticci D., Haeffner F., Orrenius C., Norin T., Hult K. J. Mol. Catal. B: Enzym. 5:1998;267.
112. Rotticci D., Orrenius C., Hult K., Norin T. Tetrahedron: Asymmetry. 8:1997;359.
113. Marnett L.J. Curr. Opin. Chem. Biol. 4:2000;545.
114. Malkowski M.G., Ginell S.L., Smith W.L., Garavito R.M. Science. 289:2000;1933.
115. Schneider W.P., Morge R.A., Henson B.E. J. Am. Chem. Soc. 99:1977;6062.
116. Schneider W.P., Bundy G.L., Lincoln F.H., Daniels E.G., Pike J.E. J. Am. Chem. Soc. 99:1977;1222.
117. Coll J.C. Chem. Rev. 92:1992;613.
118. Carmely S., Kashman Y., Loya Y., Benayahu Y. Tetrahedron Lett. 21:1980;875.
119. Valmsen K., Järving I., Boeglin W.E., Varvas K., Koljak R., Pehk T., Brash A.R., Samel N. PNAS. 98:2001;7700.
120. Koljak R., Lopp A., Pehk T., Varvas K., Müürisepp A.-M., Järving I., Samel N. Tetrahedron. 54:1998;179.
121. Jäälaid R., Järving I., Pehk T., Parve O., Lille Ü. Nat. Prod. Lett. 15:2001;221.
122. Lee D., Kim K.-C., Kim M.-J. Tetrahedron Lett. 39:1998;9039.
123. Gargouri Y., Ransac S., Verger R. BBA. 1344:1997;6.
124. S. Patkar, F. Björkling, Lipases - their structure, biochemistry and application, in: P. Nolley, S.B. Petersen (Eds.), Lipase Inhibitors, Cambridge University Press, Cambridge, 1994 (Chapter 10).
125. Chiou A., Verger R., Kokotos G. Lipids. 36:2001;535.
126. Chiou A., Markidis T., Constantinou-Kokotou V., Verger R., Kokotos G. Org. Lett. 2:2000;347.
127. Kotsovolou S., Chiou A., Verger R., Kokotos G. J. Org. Chem. 66:2001;962.
128. Kokotos G., Verger R., Chiou A. Chem. Eur. J. 6:2000;4211.
129. Kokotos G., Kotsovolou S., Constantinou-Kokotou V., Wu G., Olivecrona G. Bioorg. Med. Chem. Lett. 10:2000;2803.
130. Gatto M.T., Falcocchio S., Grippa E., Mazzanti G., Battinelli L., Nicolosi G., Lambusta D., Saso L. Bioorg. Med. Chem. 10:2002;269.