Biotransformations in the Synthesis of Enantiopure Bioactive Molecules

Accounts of Chemical Research

Volumn 31, Issue 6, 1998, Pages 333-341

  Johnson, Carl R ^a,b,c,d,e,f  

^a WAYNE STATE UNIVERSITY   (United States)

^b Medical College of Virginia ^*  (United States)

^c VIRGINIA COMMONWEALTH UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^e HARVARD UNIVERSITY   (United States)

^f ACS Organic Division   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000085691     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar970013q     Document Type: Article

References (98)

1. (1) For recent specialized books see: (a) Faber, K. Biotransformations in Organic Chemistry, Springer-Verlag: Berlin, Heidelberg, 1997. (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd.: Oxford, 1994. (c) Faber, K.; Griengl, H. In Chirality - From Weak Bosons to the α-Helix; Janoschek, R., Ed.; Springer-Verlag: Berlin Heidelberg, 1991; pp 103-140. (d) Servi, S. Microbial Reagents in Organic Synthesis; NATO ASI Series C; Kluwer: Dordrecht, 1992. (e) Abramowicz, D. A., Ed. Biocatalysis; Van Nostrand Reinhold: New York, 1990. (f) Drauz, K., Waldmann, H., Eds. Enzyme Catalysis in Organic Synthesis Vol. 1 & 2; VCH: Weinheim, 1995. (g) Gerhartz, W., Ed. Enzymes in Industry; VCH: Weinheim, 1990. (h) Sheldon, R. A. Chirotechnology: Industrial Syntheses of Optically Active Compounds; Marcel Dekker, Inc.: New York, 1993.
2. For recent specialized books see: (a) Faber, K. Biotransformations in Organic Chemistry, Springer-Verlag: Berlin, Heidelberg, 1997. (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd.: Oxford, 1994. (c) Faber, K.; Griengl, H. In Chirality - From Weak Bosons to the α-Helix; Janoschek, R., Ed.; Springer-Verlag: Berlin Heidelberg, 1991; pp 103-140. (d) Servi, S. Microbial Reagents in Organic Synthesis; NATO ASI Series C; Kluwer: Dordrecht, 1992. (e) Abramowicz, D. A., Ed. Biocatalysis; Van Nostrand Reinhold: New York, 1990. (f) Drauz, K., Waldmann, H., Eds. Enzyme Catalysis in Organic Synthesis Vol. 1 & 2; VCH: Weinheim, 1995. (g) Gerhartz, W., Ed. Enzymes in Industry; VCH: Weinheim, 1990. (h) Sheldon, R. A. Chirotechnology: Industrial Syntheses of Optically Active Compounds; Marcel Dekker, Inc.: New York, 1993.
3. For recent specialized books see: (a) Faber, K. Biotransformations in Organic Chemistry, Springer-Verlag: Berlin, Heidelberg, 1997. (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd.: Oxford, 1994. (c) Faber, K.; Griengl, H. In Chirality - From Weak Bosons to the α-Helix; Janoschek, R., Ed.; Springer-Verlag: Berlin Heidelberg, 1991; pp 103-140. (d) Servi, S. Microbial Reagents in Organic Synthesis; NATO ASI Series C; Kluwer: Dordrecht, 1992. (e) Abramowicz, D. A., Ed. Biocatalysis; Van Nostrand Reinhold: New York, 1990. (f) Drauz, K., Waldmann, H., Eds. Enzyme Catalysis in Organic Synthesis Vol. 1 & 2; VCH: Weinheim, 1995. (g) Gerhartz, W., Ed. Enzymes in Industry; VCH: Weinheim, 1990. (h) Sheldon, R. A. Chirotechnology: Industrial Syntheses of Optically Active Compounds; Marcel Dekker, Inc.: New York, 1993.
4. For recent specialized books see: (a) Faber, K. Biotransformations in Organic Chemistry, Springer-Verlag: Berlin, Heidelberg, 1997. (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd.: Oxford, 1994. (c) Faber, K.; Griengl, H. In Chirality - From Weak Bosons to the α-Helix; Janoschek, R., Ed.; Springer-Verlag: Berlin Heidelberg, 1991; pp 103-140. (d) Servi, S. Microbial Reagents in Organic Synthesis; NATO ASI Series C; Kluwer: Dordrecht, 1992. (e) Abramowicz, D. A., Ed. Biocatalysis; Van Nostrand Reinhold: New York, 1990. (f) Drauz, K., Waldmann, H., Eds. Enzyme Catalysis in Organic Synthesis Vol. 1 & 2; VCH: Weinheim, 1995. (g) Gerhartz, W., Ed. Enzymes in Industry; VCH: Weinheim, 1990. (h) Sheldon, R. A. Chirotechnology: Industrial Syntheses of Optically Active Compounds; Marcel Dekker, Inc.: New York, 1993.
5. For recent specialized books see: (a) Faber, K. Biotransformations in Organic Chemistry, Springer-Verlag: Berlin, Heidelberg, 1997. (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd.: Oxford, 1994. (c) Faber, K.; Griengl, H. In Chirality - From Weak Bosons to the α-Helix; Janoschek, R., Ed.; Springer-Verlag: Berlin Heidelberg, 1991; pp 103-140. (d) Servi, S. Microbial Reagents in Organic Synthesis; NATO ASI Series C; Kluwer: Dordrecht, 1992. (e) Abramowicz, D. A., Ed. Biocatalysis; Van Nostrand Reinhold: New York, 1990. (f) Drauz, K., Waldmann, H., Eds. Enzyme Catalysis in Organic Synthesis Vol. 1 & 2; VCH: Weinheim, 1995. (g) Gerhartz, W., Ed. Enzymes in Industry; VCH: Weinheim, 1990. (h) Sheldon, R. A. Chirotechnology: Industrial Syntheses of Optically Active Compounds; Marcel Dekker, Inc.: New York, 1993.
6. For recent specialized books see: (a) Faber, K. Biotransformations in Organic Chemistry, Springer-Verlag: Berlin, Heidelberg, 1997. (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd.: Oxford, 1994. (c) Faber, K.; Griengl, H. In Chirality - From Weak Bosons to the α-Helix; Janoschek, R., Ed.; Springer-Verlag: Berlin Heidelberg, 1991; pp 103-140. (d) Servi, S. Microbial Reagents in Organic Synthesis; NATO ASI Series C; Kluwer: Dordrecht, 1992. (e) Abramowicz, D. A., Ed. Biocatalysis; Van Nostrand Reinhold: New York, 1990. (f) Drauz, K., Waldmann, H., Eds. Enzyme Catalysis in Organic Synthesis Vol. 1 & 2; VCH: Weinheim, 1995. (g) Gerhartz, W., Ed. Enzymes in Industry; VCH: Weinheim, 1990. (h) Sheldon, R. A. Chirotechnology: Industrial Syntheses of Optically Active Compounds; Marcel Dekker, Inc.: New York, 1993.
7. For recent specialized books see: (a) Faber, K. Biotransformations in Organic Chemistry, Springer-Verlag: Berlin, Heidelberg, 1997. (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd.: Oxford, 1994. (c) Faber, K.; Griengl, H. In Chirality - From Weak Bosons to the α-Helix; Janoschek, R., Ed.; Springer-Verlag: Berlin Heidelberg, 1991; pp 103-140. (d) Servi, S. Microbial Reagents in Organic Synthesis; NATO ASI Series C; Kluwer: Dordrecht, 1992. (e) Abramowicz, D. A., Ed. Biocatalysis; Van Nostrand Reinhold: New York, 1990. (f) Drauz, K., Waldmann, H., Eds. Enzyme Catalysis in Organic Synthesis Vol. 1 & 2; VCH: Weinheim, 1995. (g) Gerhartz, W., Ed. Enzymes in Industry; VCH: Weinheim, 1990. (h) Sheldon, R. A. Chirotechnology: Industrial Syntheses of Optically Active Compounds; Marcel Dekker, Inc.: New York, 1993.
8. For recent specialized books see: (a) Faber, K. Biotransformations in Organic Chemistry, Springer-Verlag: Berlin, Heidelberg, 1997. (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Elsevier Science Ltd.: Oxford, 1994. (c) Faber, K.; Griengl, H. In Chirality - From Weak Bosons to the α-Helix; Janoschek, R., Ed.; Springer-Verlag: Berlin Heidelberg, 1991; pp 103-140. (d) Servi, S. Microbial Reagents in Organic Synthesis; NATO ASI Series C; Kluwer: Dordrecht, 1992. (e) Abramowicz, D. A., Ed. Biocatalysis; Van Nostrand Reinhold: New York, 1990. (f) Drauz, K., Waldmann, H., Eds. Enzyme Catalysis in Organic Synthesis Vol. 1 & 2; VCH: Weinheim, 1995. (g) Gerhartz, W., Ed. Enzymes in Industry; VCH: Weinheim, 1990. (h) Sheldon, R. A. Chirotechnology: Industrial Syntheses of Optically Active Compounds; Marcel Dekker, Inc.: New York, 1993.
9. (2) For recent special issues of periodicals see: (a) Proceedings of the European Symposium on Biocatalysis, Graz 1993; Crout, D. H. G., Griengl, H., Faber, K., Roberts, S. M., Eds. Biocatalysis 1994, 9 (1-4). (b) Proceedings of the International Bioorganic Symposium "Biotransformations in Organic Chemistry: Principles and Applications", Interlaken 1993; Kieslich, K., Leuenberger, H. G. W., Seebach, D., Eds. Chimia 1993, 47 (4). (c) Enzymes in Organic Synthesis; Crout, D. H. G., Roberts, S. M., Jones, J. B., Eds. Tetrahedron: Asymmetry 1993, 4 (5-6). (d) Biocatalysis in Organic Chemistry; Meijer, E. M., Ed. Recl. Trav. Chim. Pays-Bas 1991, 110 (5). (e) Enantioselective Synthesis using Biological Systems; Azerad, R., Sih, C. J., Eds. Biocatalysis 1990, 3 (1-2).
10. For recent special issues of periodicals see: (a) Proceedings of the European Symposium on Biocatalysis, Graz 1993; Crout, D. H. G., Griengl, H., Faber, K., Roberts, S. M., Eds. Biocatalysis 1994, 9 (1-4). (b) Proceedings of the International Bioorganic Symposium "Biotransformations in Organic Chemistry: Principles and Applications", Interlaken 1993; Kieslich, K., Leuenberger, H. G. W., Seebach, D., Eds. Chimia 1993, 47 (4). (c) Enzymes in Organic Synthesis; Crout, D. H. G., Roberts, S. M., Jones, J. B., Eds. Tetrahedron: Asymmetry 1993, 4 (5-6). (d) Biocatalysis in Organic Chemistry; Meijer, E. M., Ed. Recl. Trav. Chim. Pays-Bas 1991, 110 (5). (e) Enantioselective Synthesis using Biological Systems; Azerad, R., Sih, C. J., Eds. Biocatalysis 1990, 3 (1-2).
11. For recent special issues of periodicals see: (a) Proceedings of the European Symposium on Biocatalysis, Graz 1993; Crout, D. H. G., Griengl, H., Faber, K., Roberts, S. M., Eds. Biocatalysis 1994, 9 (1-4). (b) Proceedings of the International Bioorganic Symposium "Biotransformations in Organic Chemistry: Principles and Applications", Interlaken 1993; Kieslich, K., Leuenberger, H. G. W., Seebach, D., Eds. Chimia 1993, 47 (4). (c) Enzymes in Organic Synthesis; Crout, D. H. G., Roberts, S. M., Jones, J. B., Eds. Tetrahedron: Asymmetry 1993, 4 (5-6). (d) Biocatalysis in Organic Chemistry; Meijer, E. M., Ed. Recl. Trav. Chim. Pays-Bas 1991, 110 (5). (e) Enantioselective Synthesis using Biological Systems; Azerad, R., Sih, C. J., Eds. Biocatalysis 1990, 3 (1-2).
12. For recent special issues of periodicals see: (a) Proceedings of the European Symposium on Biocatalysis, Graz 1993; Crout, D. H. G., Griengl, H., Faber, K., Roberts, S. M., Eds. Biocatalysis 1994, 9 (1-4). (b) Proceedings of the International Bioorganic Symposium "Biotransformations in Organic Chemistry: Principles and Applications", Interlaken 1993; Kieslich, K., Leuenberger, H. G. W., Seebach, D., Eds. Chimia 1993, 47 (4). (c) Enzymes in Organic Synthesis; Crout, D. H. G., Roberts, S. M., Jones, J. B., Eds. Tetrahedron: Asymmetry 1993, 4 (5-6). (d) Biocatalysis in Organic Chemistry; Meijer, E. M., Ed. Recl. Trav. Chim. Pays-Bas 1991, 110 (5). (e) Enantioselective Synthesis using Biological Systems; Azerad, R., Sih, C. J., Eds. Biocatalysis 1990, 3 (1-2).
13. For recent special issues of periodicals see: (a) Proceedings of the European Symposium on Biocatalysis, Graz 1993; Crout, D. H. G., Griengl, H., Faber, K., Roberts, S. M., Eds. Biocatalysis 1994, 9 (1-4). (b) Proceedings of the International Bioorganic Symposium "Biotransformations in Organic Chemistry: Principles and Applications", Interlaken 1993; Kieslich, K., Leuenberger, H. G. W., Seebach, D., Eds. Chimia 1993, 47 (4). (c) Enzymes in Organic Synthesis; Crout, D. H. G., Roberts, S. M., Jones, J. B., Eds. Tetrahedron: Asymmetry 1993, 4 (5-6). (d) Biocatalysis in Organic Chemistry; Meijer, E. M., Ed. Recl. Trav. Chim. Pays-Bas 1991, 110 (5). (e) Enantioselective Synthesis using Biological Systems; Azerad, R., Sih, C. J., Eds. Biocatalysis 1990, 3 (1-2).
14. For recent special issues of periodicals see: (a) Proceedings of the European Symposium on Biocatalysis, Graz 1993; Crout, D. H. G., Griengl, H., Faber, K., Roberts, S. M., Eds. Biocatalysis 1994, 9 (1-4). (b) Proceedings of the International Bioorganic Symposium "Biotransformations in Organic Chemistry: Principles and Applications", Interlaken 1993; Kieslich, K., Leuenberger, H. G. W., Seebach, D., Eds. Chimia 1993, 47 (4). (c) Enzymes in Organic Synthesis; Crout, D. H. G., Roberts, S. M., Jones, J. B., Eds. Tetrahedron: Asymmetry 1993, 4 (5-6). (d) Biocatalysis in Organic Chemistry; Meijer, E. M., Ed. Recl. Trav. Chim. Pays-Bas 1991, 110 (5). (e) Enantioselective Synthesis using Biological Systems; Azerad, R., Sih, C. J., Eds. Biocatalysis 1990, 3 (1-2).
15. For recent special issues of periodicals see: (a) Proceedings of the European Symposium on Biocatalysis, Graz 1993; Crout, D. H. G., Griengl, H., Faber, K., Roberts, S. M., Eds. Biocatalysis 1994, 9 (1-4). (b) Proceedings of the International Bioorganic Symposium "Biotransformations in Organic Chemistry: Principles and Applications", Interlaken 1993; Kieslich, K., Leuenberger, H. G. W., Seebach, D., Eds. Chimia 1993, 47 (4). (c) Enzymes in Organic Synthesis; Crout, D. H. G., Roberts, S. M., Jones, J. B., Eds. Tetrahedron: Asymmetry 1993, 4 (5-6). (d) Biocatalysis in Organic Chemistry; Meijer, E. M., Ed. Recl. Trav. Chim. Pays-Bas 1991, 110 (5). (e) Enantioselective Synthesis using Biological Systems; Azerad, R., Sih, C. J., Eds. Biocatalysis 1990, 3 (1-2).
16. For recent special issues of periodicals see: (a) Proceedings of the European Symposium on Biocatalysis, Graz 1993; Crout, D. H. G., Griengl, H., Faber, K., Roberts, S. M., Eds. Biocatalysis 1994, 9 (1-4). (b) Proceedings of the International Bioorganic Symposium "Biotransformations in Organic Chemistry: Principles and Applications", Interlaken 1993; Kieslich, K., Leuenberger, H. G. W., Seebach, D., Eds. Chimia 1993, 47 (4). (c) Enzymes in Organic Synthesis; Crout, D. H. G., Roberts, S. M., Jones, J. B., Eds. Tetrahedron: Asymmetry 1993, 4 (5-6). (d) Biocatalysis in Organic Chemistry; Meijer, E. M., Ed. Recl. Trav. Chim. Pays-Bas 1991, 110 (5). (e) Enantioselective Synthesis using Biological Systems; Azerad, R., Sih, C. J., Eds. Biocatalysis 1990, 3 (1-2).
17. For recent special issues of periodicals see: (a) Proceedings of the European Symposium on Biocatalysis, Graz 1993; Crout, D. H. G., Griengl, H., Faber, K., Roberts, S. M., Eds. Biocatalysis 1994, 9 (1-4). (b) Proceedings of the International Bioorganic Symposium "Biotransformations in Organic Chemistry: Principles and Applications", Interlaken 1993; Kieslich, K., Leuenberger, H. G. W., Seebach, D., Eds. Chimia 1993, 47 (4). (c) Enzymes in Organic Synthesis; Crout, D. H. G., Roberts, S. M., Jones, J. B., Eds. Tetrahedron: Asymmetry 1993, 4 (5-6). (d) Biocatalysis in Organic Chemistry; Meijer, E. M., Ed. Recl. Trav. Chim. Pays-Bas 1991, 110 (5). (e) Enantioselective Synthesis using Biological Systems; Azerad, R., Sih, C. J., Eds. Biocatalysis 1990, 3 (1-2).
18. For recent special issues of periodicals see: (a) Proceedings of the European Symposium on Biocatalysis, Graz 1993; Crout, D. H. G., Griengl, H., Faber, K., Roberts, S. M., Eds. Biocatalysis 1994, 9 (1-4). (b) Proceedings of the International Bioorganic Symposium "Biotransformations in Organic Chemistry: Principles and Applications", Interlaken 1993; Kieslich, K., Leuenberger, H. G. W., Seebach, D., Eds. Chimia 1993, 47 (4). (c) Enzymes in Organic Synthesis; Crout, D. H. G., Roberts, S. M., Jones, J. B., Eds. Tetrahedron: Asymmetry 1993, 4 (5-6). (d) Biocatalysis in Organic Chemistry; Meijer, E. M., Ed. Recl. Trav. Chim. Pays-Bas 1991, 110 (5). (e) Enantioselective Synthesis using Biological Systems; Azerad, R., Sih, C. J., Eds. Biocatalysis 1990, 3 (1-2).
19. (3) For recent general reviews see: (a) Azerad, R. Bull. Soc. Chim. Fr. 1995, 132, 17. (b) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412, 521. (c) Santaniello, E.; Ferraboschi, P.; Grisenti, P; Manzocchi, A. Chem. Rev. 1992, 92, 1071. (d) Drueckhammer, D. G.; Hennen, W. J.; Pederson R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499. (e) Leuenberger, H. G. W. Pure Appl. Chem. 1990, 62, 753.
20. For recent general reviews see: (a) Azerad, R. Bull. Soc. Chim. Fr. 1995, 132, 17. (b) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412, 521. (c) Santaniello, E.; Ferraboschi, P.; Grisenti, P; Manzocchi, A. Chem. Rev. 1992, 92, 1071. (d) Drueckhammer, D. G.; Hennen, W. J.; Pederson R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499. (e) Leuenberger, H. G. W. Pure Appl. Chem. 1990, 62, 753.
21. For recent general reviews see: (a) Azerad, R. Bull. Soc. Chim. Fr. 1995, 132, 17. (b) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412, 521. (c) Santaniello, E.; Ferraboschi, P.; Grisenti, P; Manzocchi, A. Chem. Rev. 1992, 92, 1071. (d) Drueckhammer, D. G.; Hennen, W. J.; Pederson R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499. (e) Leuenberger, H. G. W. Pure Appl. Chem. 1990, 62, 753.
22. For recent general reviews see: (a) Azerad, R. Bull. Soc. Chim. Fr. 1995, 132, 17. (b) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412, 521. (c) Santaniello, E.; Ferraboschi, P.; Grisenti, P; Manzocchi, A. Chem. Rev. 1992, 92, 1071. (d) Drueckhammer, D. G.; Hennen, W. J.; Pederson R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499. (e) Leuenberger, H. G. W. Pure Appl. Chem. 1990, 62, 753.
23. For recent general reviews see: (a) Azerad, R. Bull. Soc. Chim. Fr. 1995, 132, 17. (b) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 412, 521. (c) Santaniello, E.; Ferraboschi, P.; Grisenti, P; Manzocchi, A. Chem. Rev. 1992, 92, 1071. (d) Drueckhammer, D. G.; Hennen, W. J.; Pederson R. L.; Barbas, C. F., III; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499. (e) Leuenberger, H. G. W. Pure Appl. Chem. 1990, 62, 753.
24. (4) Selected specialized reviews. Bakers yeast: (a) Csuk, R. Glänzer, B. I. Chem. Rev. 1991, 49-97. Hydrolytic enzymes: (b) Boland, W.; Fröbl, C.; Lorenz, M. Synthesis 1991, 1049-1072. (c) Faber, K.; Riva, S. Synthesis 1992, 895. Pseudomonas fluorescens lipase: (d) Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 773. Pig liver esterase: (e) Ohno, M.; Otsuka, M. Org. React. 1989, 37, 1. (f) Zhu, L.-M.; Tedford, M. C. Tetrahedron 1990, 46, 6587. Enzymes in the synthesis of chiral drugs: (g) Margolin, A. L. Enzyme Microb. Technol. 1993, 15, 266. Enzymatic protecting group techniques: (h) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911-937. Enzymatic C-C bond formation: (i) Fessner, W.-D.; Walter, C. Topics in Current Chemistry, Springer-Verlag: Berlin, 1996; Vol. 184.
25. Selected specialized reviews. Bakers yeast: (a) Csuk, R. Glänzer, B. I. Chem. Rev. 1991, 49-97. Hydrolytic enzymes: (b) Boland, W.; Fröbl, C.; Lorenz, M. Synthesis 1991, 1049-1072. (c) Faber, K.; Riva, S. Synthesis 1992, 895. Pseudomonas fluorescens lipase: (d) Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 773. Pig liver esterase: (e) Ohno, M.; Otsuka, M. Org. React. 1989, 37, 1. (f) Zhu, L.-M.; Tedford, M. C. Tetrahedron 1990, 46, 6587. Enzymes in the synthesis of chiral drugs: (g) Margolin, A. L. Enzyme Microb. Technol. 1993, 15, 266. Enzymatic protecting group techniques: (h) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911-937. Enzymatic C-C bond formation: (i) Fessner, W.-D.; Walter, C. Topics in Current Chemistry, Springer-Verlag: Berlin, 1996; Vol. 184.
26. Selected specialized reviews. Bakers yeast: (a) Csuk, R. Glänzer, B. I. Chem. Rev. 1991, 49-97. Hydrolytic enzymes: (b) Boland, W.; Fröbl, C.; Lorenz, M. Synthesis 1991, 1049-1072. (c) Faber, K.; Riva, S. Synthesis 1992, 895. Pseudomonas fluorescens lipase: (d) Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 773. Pig liver esterase: (e) Ohno, M.; Otsuka, M. Org. React. 1989, 37, 1. (f) Zhu, L.-M.; Tedford, M. C. Tetrahedron 1990, 46, 6587. Enzymes in the synthesis of chiral drugs: (g) Margolin, A. L. Enzyme Microb. Technol. 1993, 15, 266. Enzymatic protecting group techniques: (h) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911-937. Enzymatic C-C bond formation: (i) Fessner, W.-D.; Walter, C. Topics in Current Chemistry, Springer-Verlag: Berlin, 1996; Vol. 184.
27. Selected specialized reviews. Bakers yeast: (a) Csuk, R. Glänzer, B. I. Chem. Rev. 1991, 49-97. Hydrolytic enzymes: (b) Boland, W.; Fröbl, C.; Lorenz, M. Synthesis 1991, 1049-1072. (c) Faber, K.; Riva, S. Synthesis 1992, 895. Pseudomonas fluorescens lipase: (d) Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 773. Pig liver esterase: (e) Ohno, M.; Otsuka, M. Org. React. 1989, 37, 1. (f) Zhu, L.-M.; Tedford, M. C. Tetrahedron 1990, 46, 6587. Enzymes in the synthesis of chiral drugs: (g) Margolin, A. L. Enzyme Microb. Technol. 1993, 15, 266. Enzymatic protecting group techniques: (h) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911-937. Enzymatic C-C bond formation: (i) Fessner, W.-D.; Walter, C. Topics in Current Chemistry, Springer-Verlag: Berlin, 1996; Vol. 184.
28. Selected specialized reviews. Bakers yeast: (a) Csuk, R. Glänzer, B. I. Chem. Rev. 1991, 49-97. Hydrolytic enzymes: (b) Boland, W.; Fröbl, C.; Lorenz, M. Synthesis 1991, 1049-1072. (c) Faber, K.; Riva, S. Synthesis 1992, 895. Pseudomonas fluorescens lipase: (d) Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 773. Pig liver esterase: (e) Ohno, M.; Otsuka, M. Org. React. 1989, 37, 1. (f) Zhu, L.-M.; Tedford, M. C. Tetrahedron 1990, 46, 6587. Enzymes in the synthesis of chiral drugs: (g) Margolin, A. L. Enzyme Microb. Technol. 1993, 15, 266. Enzymatic protecting group techniques: (h) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911-937. Enzymatic C-C bond formation: (i) Fessner, W.-D.; Walter, C. Topics in Current Chemistry, Springer-Verlag: Berlin, 1996; Vol. 184.
29. Selected specialized reviews. Bakers yeast: (a) Csuk, R. Glänzer, B. I. Chem. Rev. 1991, 49-97. Hydrolytic enzymes: (b) Boland, W.; Fröbl, C.; Lorenz, M. Synthesis 1991, 1049-1072. (c) Faber, K.; Riva, S. Synthesis 1992, 895. Pseudomonas fluorescens lipase: (d) Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 773. Pig liver esterase: (e) Ohno, M.; Otsuka, M. Org. React. 1989, 37, 1. (f) Zhu, L.-M.; Tedford, M. C. Tetrahedron 1990, 46, 6587. Enzymes in the synthesis of chiral drugs: (g) Margolin, A. L. Enzyme Microb. Technol. 1993, 15, 266. Enzymatic protecting group techniques: (h) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911-937. Enzymatic C-C bond formation: (i) Fessner, W.-D.; Walter, C. Topics in Current Chemistry, Springer-Verlag: Berlin, 1996; Vol. 184.
30. Selected specialized reviews. Bakers yeast: (a) Csuk, R. Glänzer, B. I. Chem. Rev. 1991, 49-97. Hydrolytic enzymes: (b) Boland, W.; Fröbl, C.; Lorenz, M. Synthesis 1991, 1049-1072. (c) Faber, K.; Riva, S. Synthesis 1992, 895. Pseudomonas fluorescens lipase: (d) Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 773. Pig liver esterase: (e) Ohno, M.; Otsuka, M. Org. React. 1989, 37, 1. (f) Zhu, L.-M.; Tedford, M. C. Tetrahedron 1990, 46, 6587. Enzymes in the synthesis of chiral drugs: (g) Margolin, A. L. Enzyme Microb. Technol. 1993, 15, 266. Enzymatic protecting group techniques: (h) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911-937. Enzymatic C-C bond formation: (i) Fessner, W.-D.; Walter, C. Topics in Current Chemistry, Springer-Verlag: Berlin, 1996; Vol. 184.
31. Selected specialized reviews. Bakers yeast: (a) Csuk, R. Glänzer, B. I. Chem. Rev. 1991, 49-97. Hydrolytic enzymes: (b) Boland, W.; Fröbl, C.; Lorenz, M. Synthesis 1991, 1049-1072. (c) Faber, K.; Riva, S. Synthesis 1992, 895. Pseudomonas fluorescens lipase: (d) Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 773. Pig liver esterase: (e) Ohno, M.; Otsuka, M. Org. React. 1989, 37, 1. (f) Zhu, L.-M.; Tedford, M. C. Tetrahedron 1990, 46, 6587. Enzymes in the synthesis of chiral drugs: (g) Margolin, A. L. Enzyme Microb. Technol. 1993, 15, 266. Enzymatic protecting group techniques: (h) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911-937. Enzymatic C-C bond formation: (i) Fessner, W.-D.; Walter, C. Topics in Current Chemistry, Springer-Verlag: Berlin, 1996; Vol. 184.
32. Selected specialized reviews. Bakers yeast: (a) Csuk, R. Glänzer, B. I. Chem. Rev. 1991, 49-97. Hydrolytic enzymes: (b) Boland, W.; Fröbl, C.; Lorenz, M. Synthesis 1991, 1049-1072. (c) Faber, K.; Riva, S. Synthesis 1992, 895. Pseudomonas fluorescens lipase: (d) Xie, Z.-F. Tetrahedron: Asymmetry 1991, 2, 773. Pig liver esterase: (e) Ohno, M.; Otsuka, M. Org. React. 1989, 37, 1. (f) Zhu, L.-M.; Tedford, M. C. Tetrahedron 1990, 46, 6587. Enzymes in the synthesis of chiral drugs: (g) Margolin, A. L. Enzyme Microb. Technol. 1993, 15, 266. Enzymatic protecting group techniques: (h) Waldmann, H.; Sebastian, D. Chem. Rev. 1994, 94, 911-937. Enzymatic C-C bond formation: (i) Fessner, W.-D.; Walter, C. Topics in Current Chemistry, Springer-Verlag: Berlin, 1996; Vol. 184.
33. For a discussion of the quantitation of this discrimination see: Chen, C. S.; Wu, S.H.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1987, 104, 2812.
34. (6) For recent reviews of enzymatic desymmetrizations see: (a) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron (Report) 1996, 52, 3769. (b) Danieli, B.; Lesma, G.; Passarella, D.; Riva, S. In Chiral Synthons via Enzyme-Mediated Asymmetrization of Meso Compounds in Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Padwa, A., Eds.; JAI Press Ltd.: London, 1993; p 143.
35. For recent reviews of enzymatic desymmetrizations see: (a) Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron (Report) 1996, 52, 3769. (b) Danieli, B.; Lesma, G.; Passarella, D.; Riva, S. In Chiral Synthons via Enzyme-Mediated Asymmetrization of Meso Compounds in Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Padwa, A., Eds.; JAI Press Ltd.: London, 1993; p 143.
36. (7) Jones has pioneered the mapping of active sites by evaluation of substrates. For a model of the active site of pig liver esterase based on a study of more than 100 substrates see: Provencher, L.; Wynn, H.; Jones, J. B.; Krawczyk, A. R. Tetrahedron: Asymmetry 1993, 4, 2025. For a simple model for prediction of enantioselectivity of Candida rugosa lipase see: Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656.
37. Jones has pioneered the mapping of active sites by evaluation of substrates. For a model of the active site of pig liver esterase based on a study of more than 100 substrates see: Provencher, L.; Wynn, H.; Jones, J. B.; Krawczyk, A. R. Tetrahedron: Asymmetry 1993, 4, 2025. For a simple model for prediction of enantioselectivity of Candida rugosa lipase see: Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656.
38. (a) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695.
39. (b) Klibanov, A. M. Trends Biochem. Sci. 1989, 14, 141.
40. (c) Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114.
41. (d) Zaks, A.; Klibanov, A. M. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 3192.
42. (e) Santaniello, E.; Ferraboschi, P.; Grisenti, P. Enzyme Microb. Technol. 1993, 15, 367.
43. (9) Wang, Y.-F.; Wong, C.-H. J. Org. Chem. 1988, 53, 3127. Faber, K.; Ottolina, G.; Riva, S. Biocatalysis 1993, 8, 9.
44. Wang, Y.-F.; Wong, C.-H. J. Org. Chem. 1988, 53, 3127. Faber, K.; Ottolina, G.; Riva, S. Biocatalysis 1993, 8, 9.
45. Roberts, S. M., Wiggins, K., Casy, G., Eds. Preparative Biotransformations: Whole Cells and Isolated Enzymes; Wiley: Chichester, 1993.
46. Johnson, C. R.; Bis, S. J. Tetrahedron Lett. 1992, 33, 7287.
47. Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014; U.S. Patent 5,359,110, 1994.
48. Johnson, C. R.; Penning, T. D. J. Am. Chem. Soc. 1988, 110, 4726; U.S. Patent 4,873,360, 1989.
49. Parry, R. J.; Haridas, K.; De Jong, R. L.; Johnson, C. R. Tetrahedron Lett. 1990, 31, 7549.
50. Parry, R. J.; Haridas, K.; De Jong, R. L.; Johnson, C. R. Chem. Commun. 1991, 10, 740.
51. Johnson, C. R.; Nerurkar, B. M.; Golebiowski, A.; Sundram, H.; Esker, J. L. Chem. Commun. 1995, 1139.
52. Johnson, C. R.; Golebiowski, A.; Braun, M. P.; Sundram, H. Tetrahedron Lett. 1994, 35, 1833.
53. Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem. 1994, 59, 5854.
54. Medich, J.; Kunen, K.; Johnson, C. R. Tetrahedron Lett. 1987, 28, 4131.
55. Siddiqi, S. M.; Jacobson, K. A.; Esker, J. L.; Olah, M. E.; Ji, X.-d.; Melman, N.; Tiwari, K. N.; Secrist, J. A., III; Schneller, S. W.; Cristalli, G.; Stiles, G. L.; Johnson, C. R.; Ijzerman, A. P. J. Med. Chem. 1995, 38, 1174.
56. Johnson, C. R.; De Jong, R. L. Unpublished results.
57. Johnson, C. R.; Golebiowski, A.; Schoffers, E.; Sundram, H.; Braun, M. P. Synlett 1995, 313.
58. Gibson, D. T.; Hensley, M.: Yoshioka, H. Mabry, T. J. Biochemistry 1970, 9, 1626.
59. (24) For recent reviews of the use of diols obtained by microbiological oxidations of arenes see: Hudlicky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993-2000. Carless, H. A. J. Tetrahdron: Asymmetry 1992, 3, 795. Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1996, 626, 180. Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3.
60. For recent reviews of the use of diols obtained by microbiological oxidations of arenes see: Hudlicky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993-2000. Carless, H. A. J. Tetrahdron: Asymmetry 1992, 3, 795. Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1996, 626, 180. Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3.
61. For recent reviews of the use of diols obtained by microbiological oxidations of arenes see: Hudlicky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993-2000. Carless, H. A. J. Tetrahdron: Asymmetry 1992, 3, 795. Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1996, 626, 180. Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3.
62. For recent reviews of the use of diols obtained by microbiological oxidations of arenes see: Hudlicky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993-2000. Carless, H. A. J. Tetrahdron: Asymmetry 1992, 3, 795. Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1996, 626, 180. Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3.
63. For recent reviews of the use of diols obtained by microbiological oxidations of arenes see: Hudlicky, T.; Thorpe, A. J. Chem. Commun. 1996, 1993-2000. Carless, H. A. J. Tetrahdron: Asymmetry 1992, 3, 795. Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195. Hudlicky, T. In Green Chemistry: Designing Chemistry for the Environment; Anastas, P. T., Williamson, T., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 1996, 626, 180. Widdowson, D. A.; Ribbons, D. W.; Thomas, S. D. Janssen Chim. Acta 1990, 8, 3.
64. (a) Johnson, C. R.; Plé, P. A.; Su, L.; Heeg, M. J.; Adams, J. P. Synlett 1992, 388-390.
65. (b) Johnson, C. R.; Adams, J. P.; Collins, M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1.
66. (26) For example, the diols derived from toluene and chlorobenzene have been transformed to enone (+)-6 (Hudlicky, T.; Luna, H.; Barbieri, G.; Kwart, L.D. J. Am. Chem. Soc. 1988, 110, 4735. Hudlicky, T.; Natchus, M. G.; Nugent, T. Synth. Commun. 1992, 22, 151).
67. For example, the diols derived from toluene and chlorobenzene have been transformed to enone (+)-6 (Hudlicky, T.; Luna, H.; Barbieri, G.; Kwart, L.D. J. Am. Chem. Soc. 1988, 110, 4735. Hudlicky, T.; Natchus, M. G.; Nugent, T. Synth. Commun. 1992, 22, 151).
68. Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1995, 36, 653.
69. (28) For a detailed discussion of the oxidative cleavage/ recyclization strategy with regard to the synthesis of carbohydrates and related substances see: Hudlicky, T. Chem. Rev. 1996, 96, 3. Hudlicky, T. Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: London, 1995; Vol. 1, p 271.
70. For a detailed discussion of the oxidative cleavage/ recyclization strategy with regard to the synthesis of carbohydrates and related substances see: Hudlicky, T. Chem. Rev. 1996, 96, 3. Hudlicky, T. Reed, J. W. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: London, 1995; Vol. 1, p 271.
71. Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991.
72. Johns, B. A.; Elbein, A. D.; Pan, Y. T.; Johnson, C. R. J. Am. Chem. Soc. 1997, 119, 4856.
73. Johnson, C. R.; Johns, B. A. J. Org. Chem. 1997, 62, 6046.
74. Johnson, C. R.; Johns, B. A. Synlett 1997, 1406.
75. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977.
76. Johnson, C. R.; Johns, B. A., Tetrahedron Lett. 1998, 39, 749.
77. Johnson, C. R.; Golebiowski, A.; McGill, T. K. Steensma, D. H. Tetrahedron Lett. 1991, 32, 2597.
78. Johnson, C. R.; Senanayake, C. H. J. Org. Chem. 1989, 54, 735.
79. Scialdone, M. A.; Johnson, C. R. Tetrahedron Lett. 1995, 36, 43.
80. Johnson, C. R.; Golebiowski, A.; Steensma, D. H. Tetrahedron Lett. 1991, 32, 3931.
81. Johnson, C. R..; Golebiowski, A.; Steensma, D. H. J. Am. Chem. Soc. 1992, 114, 9414.
82. Johnson, C. R.; Kozak, J. J. Org. Chem. 1994, 59, 2910.
83. Xu, Y.; Johnson, C. R. Tetrahedron Lett. 1997, 38, 1117.
84. Johnson, C. R.; Bis, S. J. J. Org. Chem. 1995, 60, 615.
85. Johnson, C. R.; Harikrishnan, L. S.; Golebiowski, A. Tetrahedron Lett. 1994, 35, 7735.
86. Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B.W.; Uskokovioć, M. R.; Wovkulich, P. M. Tetrahedron Lett. 1992, 33, 917.
87. Johnson, C. R.; Sakaguchi, H. Synlett 1992, 813.
88. Sundram, H; Golebiowski, A.; Johnson, C. R. Tetrahedron Lett. 1995, 35, 6975.
89. Siddiqi, S. M.; Schneller, S. W.; Ikeda, S. .; Snoeck, R.; Andrei, G.; Balzarini, J.; DeClercq, E. Nucleosides Nucleotides 1993, 12, 185.
90. Johnson, C. R.; Miller, M. W. J. Org. Chem. 1995, 60, 6674.
91. Miller, M. W.; Johnson, C. R. J. Org. Chem. 1997, 62, 1582.
92. Gorins, G.; Kuhnert, L.; Johnson, C. R.; Marnett, L. J. J. Med. Chem. 1996, 39, 4871.
93. Johnson, C. R.; Gorins, G.; Marnett, L. J.; Honn, K. V. U.S. Patent 5,238,832, 1993.
94. Nicolaou, K. C.; Ueno, H.; Liu, J.-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chaddha, R. J. Am. Chem. Soc. 1995, 117, 813 and preceding papers.
95. Johnson, C. R.; Xu, Y.; Nicolaou, K. C.; Yang, Z.; Guy, R. K.; Dong, J. G.; Berova, N. Tetrahedron Lett. 1995, 36, 3291.
96. (54) For selected addtional examples of sequential kinetic resolutions see Guo, Z.-W.; Wu, S.-H.; Chen, C.S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1990, 112, 4943. Macfarland, E. L. A.; Roberts, S. M., Turner, N. L. Chem. Commun. 1990, 569. Chen, C.-S.; Liu, Y.-C. J. Org. Chem. 1991, 56, 1966.
97. For selected addtional examples of sequential kinetic resolutions see Guo, Z.-W.; Wu, S.-H.; Chen, C.S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1990, 112, 4943. Macfarland, E. L. A.; Roberts, S. M., Turner, N. L. Chem. Commun. 1990, 569. Chen, C.-S.; Liu, Y.-C. J. Org. Chem. 1991, 56, 1966.
98. For selected addtional examples of sequential kinetic resolutions see Guo, Z.-W.; Wu, S.-H.; Chen, C.S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1990, 112, 4943. Macfarland, E. L. A.; Roberts, S. M., Turner, N. L. Chem. Commun. 1990, 569. Chen, C.-S.; Liu, Y.-C. J. Org. Chem. 1991, 56, 1966.