'Designer yeast': An enantioselective oxidizing reagent for organic synthesis

Synlett

Volumn , Issue 1, 1999, Pages 153-158

  Kayser, M ^a   Chen, Gang ^c   Stewart, Jon ^b  

^a UNIVERSITY OF NEW BRUNSWICK   (Canada)

^b University of Florida ^*  (United States)

^c NONE

Author keywords

Baeyer Villiger oxidation; Biocatalysis; Chiral lactones; Ketones; Recombinant yeast; Sulfoxides

Indexed keywords

KETONE DERIVATIVE; LACTONE DERIVATIVE; OXIDIZING AGENT; SULFOXIDE;

ARTICLE; CATALYSIS; NONHUMAN; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; RECOMBINANT DNA TECHNOLOGY; SYNTHESIS; YEAST;

EID: 0032911598     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2553     Document Type: Article

References (32)

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9. Review: Stewart, J. D. Curr. Org. Chem. 1997, 2, 211-232. Several groups investigated CHMO's potential for asymmetric synthesis, for example: Walsh, C. T.; Chen, Y.-C. J. Ang. Chem., Int. Ed. Engl. 1988, 27, 333-343; Taschner, M. J.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892-6893; Abril, O.; Ryerson, C.C.; Walsh, C.T.; Whitesides, G.M. Bioorg Chem. 1989, 17, 41; Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 3663-3664; Levitt, M.S.; Newton, R.F.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1990, 619; Konigsberg, K.; Alphand, V.; Furstoss, R.; Griengl, H. Tetrahedron Lett. 1991, 499; Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382; Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390; Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Perkin Trans 1 1996, 1867-1872.
10. Review: Stewart, J. D. Curr. Org. Chem. 1997, 2, 211-232. Several groups investigated CHMO's potential for asymmetric synthesis, for example: Walsh, C. T.; Chen, Y.-C. J. Ang. Chem., Int. Ed. Engl. 1988, 27, 333-343; Taschner, M. J.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892-6893; Abril, O.; Ryerson, C.C.; Walsh, C.T.; Whitesides, G.M. Bioorg Chem. 1989, 17, 41; Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 3663-3664; Levitt, M.S.; Newton, R.F.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1990, 619; Konigsberg, K.; Alphand, V.; Furstoss, R.; Griengl, H. Tetrahedron Lett. 1991, 499; Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382; Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390; Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Perkin Trans 1 1996, 1867-1872.
11. Review: Stewart, J. D. Curr. Org. Chem. 1997, 2, 211-232. Several groups investigated CHMO's potential for asymmetric synthesis, for example: Walsh, C. T.; Chen, Y.-C. J. Ang. Chem., Int. Ed. Engl. 1988, 27, 333-343; Taschner, M. J.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892-6893; Abril, O.; Ryerson, C.C.; Walsh, C.T.; Whitesides, G.M. Bioorg Chem. 1989, 17, 41; Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 3663-3664; Levitt, M.S.; Newton, R.F.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1990, 619; Konigsberg, K.; Alphand, V.; Furstoss, R.; Griengl, H. Tetrahedron Lett. 1991, 499; Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382; Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390; Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Perkin Trans 1 1996, 1867-1872.
12. Review: Stewart, J. D. Curr. Org. Chem. 1997, 2, 211-232. Several groups investigated CHMO's potential for asymmetric synthesis, for example: Walsh, C. T.; Chen, Y.-C. J. Ang. Chem., Int. Ed. Engl. 1988, 27, 333-343; Taschner, M. J.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892-6893; Abril, O.; Ryerson, C.C.; Walsh, C.T.; Whitesides, G.M. Bioorg Chem. 1989, 17, 41; Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 3663-3664; Levitt, M.S.; Newton, R.F.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1990, 619; Konigsberg, K.; Alphand, V.; Furstoss, R.; Griengl, H. Tetrahedron Lett. 1991, 499; Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382; Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390; Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Perkin Trans 1 1996, 1867-1872.
13. Review: Stewart, J. D. Curr. Org. Chem. 1997, 2, 211-232. Several groups investigated CHMO's potential for asymmetric synthesis, for example: Walsh, C. T.; Chen, Y.-C. J. Ang. Chem., Int. Ed. Engl. 1988, 27, 333-343; Taschner, M. J.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892-6893; Abril, O.; Ryerson, C.C.; Walsh, C.T.; Whitesides, G.M. Bioorg Chem. 1989, 17, 41; Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 3663-3664; Levitt, M.S.; Newton, R.F.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1990, 619; Konigsberg, K.; Alphand, V.; Furstoss, R.; Griengl, H. Tetrahedron Lett. 1991, 499; Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382; Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390; Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Perkin Trans 1 1996, 1867-1872.
14. Review: Stewart, J. D. Curr. Org. Chem. 1997, 2, 211-232. Several groups investigated CHMO's potential for asymmetric synthesis, for example: Walsh, C. T.; Chen, Y.-C. J. Ang. Chem., Int. Ed. Engl. 1988, 27, 333-343; Taschner, M. J.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892-6893; Abril, O.; Ryerson, C.C.; Walsh, C.T.; Whitesides, G.M. Bioorg Chem. 1989, 17, 41; Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 3663-3664; Levitt, M.S.; Newton, R.F.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1990, 619; Konigsberg, K.; Alphand, V.; Furstoss, R.; Griengl, H. Tetrahedron Lett. 1991, 499; Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382; Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390; Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Perkin Trans 1 1996, 1867-1872.
15. Review: Stewart, J. D. Curr. Org. Chem. 1997, 2, 211-232. Several groups investigated CHMO's potential for asymmetric synthesis, for example: Walsh, C. T.; Chen, Y.-C. J. Ang. Chem., Int. Ed. Engl. 1988, 27, 333-343; Taschner, M. J.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892-6893; Abril, O.; Ryerson, C.C.; Walsh, C.T.; Whitesides, G.M. Bioorg Chem. 1989, 17, 41; Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 3663-3664; Levitt, M.S.; Newton, R.F.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1990, 619; Konigsberg, K.; Alphand, V.; Furstoss, R.; Griengl, H. Tetrahedron Lett. 1991, 499; Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382; Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390; Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Perkin Trans 1 1996, 1867-1872.
16. Review: Stewart, J. D. Curr. Org. Chem. 1997, 2, 211-232. Several groups investigated CHMO's potential for asymmetric synthesis, for example: Walsh, C. T.; Chen, Y.-C. J. Ang. Chem., Int. Ed. Engl. 1988, 27, 333-343; Taschner, M. J.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892-6893; Abril, O.; Ryerson, C.C.; Walsh, C.T.; Whitesides, G.M. Bioorg Chem. 1989, 17, 41; Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 3663-3664; Levitt, M.S.; Newton, R.F.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1990, 619; Konigsberg, K.; Alphand, V.; Furstoss, R.; Griengl, H. Tetrahedron Lett. 1991, 499; Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382; Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390; Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Perkin Trans 1 1996, 1867-1872.
17. Review: Stewart, J. D. Curr. Org. Chem. 1997, 2, 211-232. Several groups investigated CHMO's potential for asymmetric synthesis, for example: Walsh, C. T.; Chen, Y.-C. J. Ang. Chem., Int. Ed. Engl. 1988, 27, 333-343; Taschner, M. J.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892-6893; Abril, O.; Ryerson, C.C.; Walsh, C.T.; Whitesides, G.M. Bioorg Chem. 1989, 17, 41; Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 3663-3664; Levitt, M.S.; Newton, R.F.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1990, 619; Konigsberg, K.; Alphand, V.; Furstoss, R.; Griengl, H. Tetrahedron Lett. 1991, 499; Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382; Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390; Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Perkin Trans 1 1996, 1867-1872.
18. Review: Stewart, J. D. Curr. Org. Chem. 1997, 2, 211-232. Several groups investigated CHMO's potential for asymmetric synthesis, for example: Walsh, C. T.; Chen, Y.-C. J. Ang. Chem., Int. Ed. Engl. 1988, 27, 333-343; Taschner, M. J.; Black, D. J. J. Am. Chem. Soc. 1988, 110, 6892-6893; Abril, O.; Ryerson, C.C.; Walsh, C.T.; Whitesides, G.M. Bioorg Chem. 1989, 17, 41; Alphand, V.; Archelas, A.; Furstoss, R. Tetrahedron Lett. 1989, 3663-3664; Levitt, M.S.; Newton, R.F.; Roberts, S.M.; Willetts, A.J. J. Chem. Soc., Chem. Commun. 1990, 619; Konigsberg, K.; Alphand, V.; Furstoss, R.; Griengl, H. Tetrahedron Lett. 1991, 499; Alphand, V.; Furstoss, R. J. Org. Chem. 1992, 57, 1306-1309; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 1992, 3, 379-382; Taschner, M. J.; Black, D. J.; Chen, Q.-Z. Tetrahedron: Asymmetry 1993, 4, 1387-1390; Alphand, V.; Furstoss, R.; Pedragosa-Moreau, S.; Roberts, S. M.; Willetts, A. J. J. Chem. Soc. Perkin Trans 1 1996, 1867-1872.
19. Krow, G. R. Org. Reactions 1993, 43, 251-798.
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22. Stewart, J. D.; Reed, K. W.; Martinez, C. A.; Zhu, J.; Chen, G.; Kayser, M. M. J. Am. Chem. Soc. 1998, 120, 3541-3548.
23. Kayser, M. M.; Chen, G.; Stewart, J. D. J. Org. Chem. 1998, 63, 7103-7106.
24. Kayser, M. M.; Chen, G.; Stewart, J. D. manuscript in preparation
25. Kayser, M. M.; Chen, G.; manuscript in preparation.
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28. Alphand, V.; Gaggero, N.; Colonna, S.; Pasta, P.; Furstoss, R. Tetrahedron 1997, 53, 9695-9706; Colonna, S.; Gaggero, N.; Pasta, P.; Ottolina, G. J. Chem. Soc., Chem. Commun. 1996, 2303-2307; Alphand, V.; Gaggero, N.; Colonna, S,; Furstoss, R. Tetrahedron Lett. 1996, 37, 6117-6120.
29. Alphand, V.; Gaggero, N.; Colonna, S.; Pasta, P.; Furstoss, R. Tetrahedron 1997, 53, 9695-9706; Colonna, S.; Gaggero, N.; Pasta, P.; Ottolina, G. J. Chem. Soc., Chem. Commun. 1996, 2303-2307; Alphand, V.; Gaggero, N.; Colonna, S,; Furstoss, R. Tetrahedron Lett. 1996, 37, 6117-6120.
30. Alphand, V.; Gaggero, N.; Colonna, S.; Pasta, P.; Furstoss, R. Tetrahedron 1997, 53, 9695-9706; Colonna, S.; Gaggero, N.; Pasta, P.; Ottolina, G. J. Chem. Soc., Chem. Commun. 1996, 2303-2307; Alphand, V.; Gaggero, N.; Colonna, S,; Furstoss, R. Tetrahedron Lett. 1996, 37, 6117-6120.
31. Natural baker's yeast was shown to carry out oxidations at sulfur for certain sulfides. Beecher, J.; Richardson, P.; Roberts, S. M.; Willetts, A. Biotechnology Lett. 1995, 17, 1069-1074; Tang, J.; Brackenridge, I.; Roberts, S. M.; Beecher, J.; Willetts, A., Tetrahedron, 1995, 51, 13217.
32. Natural baker's yeast was shown to carry out oxidations at sulfur for certain sulfides. Beecher, J.; Richardson, P.; Roberts, S. M.; Willetts, A. Biotechnology Lett. 1995, 17, 1069-1074; Tang, J.; Brackenridge, I.; Roberts, S. M.; Beecher, J.; Willetts, A., Tetrahedron, 1995, 51, 13217.