A Chemo-Enzymatic Synthesis of D-Allosamine Derivatives from Tri-O-acetyl- D-glucal

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 10, 1997, Pages 2535-2540

  Sugai, Takeshi ^a   Okazaki, Hanako ^a   Kuboki, Atsuhito ^a   Ohta, Hiromichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000834727     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.2535     Document Type: Article

References (89)

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41. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
42. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
43. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
44. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
45. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
46. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
47. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
48. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
49. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
50. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
51. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
52. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
53. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
54. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
55. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
56. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
57. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
58. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
59. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 108, 5638 (1986); H. M. Sweers and C.-H. Wong, J. Am. Chem. Soc., 108, 6421 (1986); J.-F. Shaw and A. M. Klibanov, Biotechnol. Bioeng., 29, 648 (1987); W. J. Hennen, H. M. Sweers, Y.-F. Wang, and C.-H. Wong, J. Org. Chem., 53, 4939 (1988); G. Carrea, S. Riva, F. Secundo, and B. Danieli, J. Chem. Soc., Perkin Trans. 1, 1989, 1057; A. Uemura, K. Nozaki, J. Yamashita, and M. Yasumoto, Tetrahedron Lett., 30, 3817 (1989); F. Theil and H. Schick, Synthesis, 1991, 533; S. Cai, S. Hakomori, and T. Toyokuni, J. Org. Chem., 57, 3431 (1992); H. K. Singh, G. L. Cote, and T. M. Hadfield, Tetrahedron Lett., 35, 1353 (1994); D. Kwoh, D. J. Pocalyko, A. J. Carchi, B. Harirchian, L. O. Hargiss, and T. C. Wong, Carbohydr. Res., 274, 111 (1995); T. Watanabe, R. Mastue, Y. Honda, and M. Kuwahara, Carbohydr. Res., 275, 215 (1995); L. F. García-Alles and V. Gotor, Tetrahedron, 51, 307 (1995); A. K. Prasad, M. D. Sørensen, V. S. Parmar, and J. Wengel, Tetrahedron Lett., 36, 6163 (1995); K.-F. Hsiao, S.-T. Chen, K.-T. Wang, and S.-H. Wu, Synlett, 1996, 966; M. Yokoyama, Y. Nakatsuka, T. Sugai, and H. Ohta, Biosci. Biotechnol. Biochem., 60, 1540 (1996). For the use of other hydrolytic enzymes, see: S. Riva, J. Chopineau, A. P. G. Kieboom, and A. M. Klibanov, J. Am. Chem. Soc., 110, 584 (1988); D. Chaplin, D. H. G. Crout, S. Bornemann, D. W. Hutchinson, and R. Khan, J. Chem. Soc., Perkin Trans. 1, 1992, 235; B. Herradón and S. Valverde, Synlett, 1995, 599. See also a review: H. Waldmann, in "Enzyme Catalysis in Organic Synthesis," ed by K. Drauz and H. Waldman, VCH, Weinheim (1995), Vol. 2, pp. 868-882.
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