Biocatalytic resolution of sterically hindered alcohols, carboxylic acids and esters containing fully substituted chiral centers by hydrolytic enzymes

Journal of Molecular Catalysis - B Enzymatic

Volumn 10, Issue 4, 2000, Pages 357-376

  Pogorevc, Mateja ^a   Faber, Kurt ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

, Disubstituted carboxylic acid; Carboxyl ester hydrolase; Enzymatic resolution; Kinetic resolution; Lipase; tert alcohol

Indexed keywords

ALCOHOLS; CARBOXYLIC ACIDS; CRYSTAL ATOMIC STRUCTURE; ENZYMES; ESTERS; HYDROLYSIS; REACTION KINETICS;

CARBOXYL ESTER HYDROLASE; ELECTROPHILICITY; LIPASE;

CATALYSIS;

ALCOHOL DERIVATIVE; CARBOXYLIC ACID; ESTER; ESTERASE; FUNCTIONAL GROUP; HYDROLASE; PROTEINASE; TRIACYLGLYCEROL LIPASE;

CATALYSIS; CHIRALITY; ENANTIOMER; ENZYME SUBSTRATE; HYDROLYSIS; REVIEW; STEREOCHEMISTRY;

EID: 0034684072     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1177(99)00121-6     Document Type: Review

References (95)

1. Jones J.B., Beck J.F. Weissberger A. Application of Biochemical Systems in Organic Chemistry. 1976;114 Wiley, New York. Ref. 6, p. 179.
2. Theil F. Chem. Rev. 95:1995;2203.
3. Santaniello E., Ferraboschi P., Grisenti P. Enzyme Microb. Technol. 15:1993;367.
4. Boland W., Frößl C., Lorenz M. Synthesis. 1991;1049.
5. Ohno M., Otsuka M. Org. React. 37:1989;1.
6. Bornscheuer U., Kazlauskas R.J. Hydrolases in Organic Synthesis - Regio and Stereoselective Biotransformations. 1999;Verlag Chemie, Weinheim.
7. Chen C.-S., Fujimoto Y., Girdaukas G., Sih C.J. J. Am. Chem. Soc. 104:1982;7294.
8. Straathof A.J.J., Jonjejan J.A. Enzyme Microb. Technol. 21:1997;559.
9. Straathof A.J.J., Rakels J.L.L., Heijnen J.J. Biocatalysis. 7:1992;13.
10. Kagan H.B., Fiaud J.C. Top. Stereochem. 18:1988;249.
11. Schultz M., Hermann P., Kunz H. Synlett. 1992;37.
12. Ohloff G., Klein E. Tetrahedron. 18:1962;37.
13. Iwai M., Okumura S., Tsujisaka Y. Agric. Biol. Chem. 44:1980;2731.
14. Okumura S., Iwai M., Tsujisaka Y. Biochim. Biophys. Acta. 575:1979;156.
15. Madyastha K.M., Krishna Murthy N.S.R. Appl. Microbiol. Biotechnol. 28:1988;324.
16. Oritani T., Yamashita K. Agric. Biol. Chem. 37:1973;1923.
17. Osprian I., Steinreiber A., Mischitz M., Faber K. Biotechnol. Lett. 18:1996;1331.
18. M. Pogorevc, U.T. Strauss, M. Hayn, K. Faber, Chem. Mon., submitted.
19. Barnier J.-P., Blanco L., Rousseau G., Guibé-Jampel E. J. Org. Chem. 58:1993;1570.
20. Morisson V., Barnier J.-P., Blanco L. Tetrahedron. 54:1998;7749.
21. Ohta H., Kimura Y., Sugano Y., Sugai T. Tetrahedron. 45:1989;5469.
22. Ohta H., Miyamae Y., Kimura Y. Chem. Lett. 1989;379.
23. O'Hagan D., Zaidi N.A. J. Chem. Soc., Perkin Trans. 1. 1992;947.
24. O'Hagan D., Zaidi N.A., Lamont R.B. Tetrahedron: Asymmetry. 4:1993;1703.
25. Zelinski T., Waldmann H. Angew. Chem., Int. Ed. Engl. 36:1997;722.
26. Lalonde J.J., Govardhan C., Khalaf N., Martinez A.G., Visuri K., Margolin A.L. J. Am. Chem. Soc. 117:1995;6845.
27. Kallwass H.K.W., Yee C., Blythe T.A., McNabb T.J., Rogers E.E., Shames S.L. Bioorg. Med. Chem. 2:1994;557.
28. Königsberger K., Prasad K., Repic O. Tetrahedron: Asymmetry. 10:1999;679.
29. O'Hagan D., Zaidi N.A. Tetrahedron: Asymmetry. 5:1994;1111.
30. Coope J.F., Main B.G. Tetrahedron: Asymmetry. 6:1995;1393.
31. Imura A., Itoh M., Miyadera A. Chem. Pharm. Bull. 46:1998;1878.
32. Faber K. Biotransformations in Organic Chemistry. 3rd edn. 1997;59-88 Springer, Heidelberg.
33. Brackenridge I., McCague R., Roberts S.M., Turner N.J. J. Chem. Soc., Perkin Trans. 1. 1993;1093.
34. Franssen M.C.R., Goetheer E.L.V., Jongejan H., de Groot A. Tetrahedron Lett. 39:1998;8345.
35. Jongejan J.A., van Tol J.B., Duine J.A. Chimicaoggi. 12:1994;15.
36. Berkowitz D.B., Pumphrey J.A., Shen Q. Tetrahedron Lett. 35:1994;8743.
37. Ferraboschi P., Brembilla D., Grisenti P., Santaniello E. J. Org. Chem. 56:1991;5478.
38. Cheong C.S., Im D.S., Kim J., Kim I.O. Biotechnol. Lett. 18:1996;1419.
39. Chen S.-T., Fang J.-M. J. Org. Chem. 62:1997;4349.
40. Hof R.P., Kellogg R.M. J. Chem. Soc., Perkin Trans. 1. 1996;2051.
41. Jimenez O., Bosch M.P., Guerrero A. J. Org. Chem. 62:1997;3486.
42. Hof R.P., Kellogg R.M. Tetrahedron: Asymmetry. 5:1994;565.
43. Hof R.P., Kellogg R.M. J. Org. Chem. 61:1996;3423.
44. Wirz B., Barner R., Hübscher J. J. Org. Chem. 58:1993;3980.
45. Akita H., Nozawa M., Umezawa I., Nagumo S. Biocatalysis. 9:1994;79.
46. Hyatt J.A., Skelton C. Tetrahedron: Asymmetry. 8:1997;523.
47. Brenna E., Fuganti C., Fuganti D., Grasselli P., Malpezzi L., Pedrocchi-Fantoni G. Tetrahedron. 53:1997;17769.
48. Ferraboschi P., Grisenti P., Manzocchi A., Santaniello E. Tetrahedron: Asymmetry. 5:1994;691.
49. Mizoguchi E., Suzuki T., Achiwa K. Synlett. 1994;929.
50. Moore A.N.J., Dutton P.J., Zahalka H.A., Burton G.W., Ingold K.U. J. Am. Chem. Soc. 117:1995;5677.
51. Strauss U.T., Felfer U., Faber K. Tetrahedron: Asymmetry. 10:1999;107.
52. Leuenberger H.G.W., Wirz B. Chimia. 47:1993;82.
53. Watanabe N., Sugai T., Ohta H. Chem. Lett. 1992;657.
54. Itoh T., Ohara H., Takagi Y., Kanda N., Uneyama K. Tetrahedron Lett. 34:1993;4215.
55. Fadel A., Arzel P. Tetrahedron: Asymmetry. 8:1997;283.
56. Jones J.B., Marr P.W. Tetrahedron Lett. 14:1973;3165.
57. Cohen S.G., Sprinzak Y., Khedouri E. J. Am. Chem. Soc. 83:1961;4225.
58. Spero D.M., Kapadia S.R. J. Org. Chem. 61:1996;7398.
59. Schoemaker H.E., Boesten W.H.J., Kaptein B., Hermes H.F.M., Sonke T., Broxterman Q.B., van den Tweel W.J.J., Kamphuis J. Pure Appl. Chem. 64:1992;1171.
60. Cativiela C., Diaz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517.
61. Chenault H.K., Dahmer J., Whitesides G.M. J. Am. Chem. Soc. 111:1989;6354.
62. Keller J.W., Hamilton B.J. Tetrahedron Lett. 27:1986;1249.
63. Kaptein B., Moody H.M., Broxterman Q.D., Kamphuis J. J. Chem. Soc., Perkin Trans. 1. 1994;1495.
64. Kallwass H.K.W., Yee C., Blythe T.A., McNabb T.J., Rogers E.E., Shames S.L. Bioorg. Med. Chem. 2:1994;557.
65. Yee C., Blythe T.A., McNabb T.J., Walts A.E. J. Org. Chem. 57:1992;3525.
66. Feichter C., Faber K., Griengl H. J. Chem. Soc., Perkin Trans. 1. 1991;653.
67. Moorlag H., Kellogg R.M., Kloosterman M., Kaptein B., Kamphuis J., Schoemaker H.H. J. Org. Chem. 55:1990;5878.
68. Moorlag H., Kellogg R.M. Tetrahedron: Asymmetry. 2:1991;705.
69. Provencher L., Wynn H., Jones J.B., Krawczyk A.R. Tetrahedron: Asymmetry. 4:1993;2025.
70. Pottie M., Van der Eycken J., Vandevalle M., Dewanckele J.M., Röper H. Tetrahedron Lett. 30:1989;5319.
71. Yang S., Hayden W., Faber K., Griengl H. Synthesis. 1992;365.
72. Tanyeli C., Sezen B., Demir A.S., Alves R.B., Arseniyadis S. Tetrahedron: Asymmetry. 10:1999;1129.
73. Helaine V., Bolte J. Tetrahedron: Asymmetry. 9:1998;3855.
74. Sugai T., Kakeya H., Ohta H. J. Org. Chem. 55:1990;4643.
75. Westermann B., Große Scharmann H., Kortmann I. Tetrahedron: Asymmetry. 4:1993;2119.
76. Westermann B., Kortmann I. Biocatalysis. 10:1994;289.
77. Bucciarelli M., Forni A., Moretti I., Prati F. J. Chem. Soc., Chem. Commun. 1988;1614.
78. Sugai T., Kakeya H., Ohta H. Tetrahedron. 1990;3463.
79. Sugai T., Watanabe N., Ohta H. Tetrahedron: Asymmetry. 2:1991;371.
80. Westermann B., Gedrath I. Synlett. 1996;665.
81. Miyazawa T., Shimaoka M., Yamada T. Biotechnol. Lett. 21:1999;309.
82. Lalonde J.J., Bergbreiter D.E., Wong C.-H. J. Org. Chem. 53:1988;2323.
83. Takeuchi Y., Itoh N., Note H., Koizumi T., Yamaguchi K. J. Am. Chem. Soc. 113:1991;6318.
84. Colton I.J., Ahmed S.N., Kazlauskas R.J. J. Org. Chem. 60:1995;212.
85. Kometani T., Isobe T., Goto M., Takeuchi Y., Haufe G. J. Mol. Catal. B. 5:1998;171.
86. Björkling F., Boutelje J., Gatenbeck S., Hult K., Norin T., Szmulik P. Tetrahedron. 41:1985;1347.
87. Tamm C. Pure Appl. Chem. 64:1992;1187.
88. Gee A.D., Langström B. J. Chem. Soc., Perkin Trans. 1. 1991;215.
89. Björkling F., Norin T., Szmulik P., Boutelje J., Hult K., Kraulis P. Biocatalysis. 1:1987;87.
90. Fadel A., Canet J.-L., Salaun J. Tetrahedron Lett. 30:1989;6687.
91. Canet J.-L., Fadel A., Salaun J. J. Org. Chem. 57:1992;3463.
92. Fadel A., Garcia-Argote S. Tetrahedron: Asymmetry. 7:1996;1159.
93. De Jeso B., Belair N., Deleuze H., Rascle M.-C., Maillard B. Tetrahedron Lett. 31:1990;653.
94. Mohr P., Waespe-Sarcevic N., Tamm C., Gawronska K., Gawronski J.K. Helv. Chim. Acta. 66:1983;2501.
95. Wilson W.K., Baca S.B., Barber Y.J., Scallen T.J., Morrow C.J. J. Org. Chem. 48:1983;3960.