Glycosidase-catalysed synthesis of glycosides by an improved procedure for reverse hydrolysis: Application to the chemoenzymatic synthesis of galactopyranosyl-(1 → 4)-O-α-galactopyranoside derivatives

Tetrahedron Asymmetry

Volumn 7, Issue 7, 1996, Pages 1973-1984

  Vic, Gabin ^a   Hastings, Jeremy J ^a   Crout, David H G ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; GALACTOSIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030200594     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00238-8     Document Type: Article

References (35)

1. 1. Toshima, H; Tatsuka, K. Chem Rev., 1993, 93, 1503-1531.
2. 2. a) Nilsson, K.G.I. Appl. Biocatalysis, 1991, 117-177;
3. b) Vic, G.; Hastings, J.J.; Howarth, O.W.; Crout, D.H.G. Tetrahedron: Asymmetry, 1996, 7(3), 709-720.
4. c) Singh, S.; Gallagher, R.; Derrick, P.J.; Crout, D.H.G. Tetrahedron: Asymmetry, 1995, 6, 2803-2810;
5. d) Singh, S.; Crout, D.H.G.; Packwood, J. Carbohydr. Res., 1995, 279, 312-325;
6. e) Singh, S.; Packwood, J.; Samuel, C.J.; Critchley, P.; Crout, D.H.G. Carbohydr. Res., 1995, 279, 293-305.
7. 3. a) Crout, D.H.G.; MacManus, D.A.; Critcley, P. J. Chem. Soc., Chem. Commun., 1991, 376-378;
8. b) Mitsuo, N.; Takeichi, H.; Satoh, T. Chem. Pharm. Bull., 1984, 32, 1183-1187;
9. c) Ooi, Y.; Hashimoto, T.; Mitsuo, N; Satoh, T. Chem. Pharm. Bull., 1985, 33, 1808-1814;
10. d) Ooi, Y.; Mitsuo, N; Satoh, T. Chem. Pharm. Bull., 1985, 33, 5547-5550;
11. e) Björkling, F.; Godtfredsen, E.E. Tetrahedron, 1988, 44, 2957-2962;
12. f) Trincone, A.; Nicolaus, B., Lama; L., Cambacorta; A. J. Chem. Soc., Perkins Trans I, 1991, 2841-2844;
13. g) Itano, K.; Yamasaki, K.; Kihara, C.; Tanaka, O. Carbohydr. Res., 1980, 87, 27-34,
14. h) Vulfson, E.N.; Patel, R.; Beacher, J.E.; Andrews, A.T.; Low, B.A. Enzyme Microbial Technol., 1990, 12, 950-954.
15. 4. a) Bourquelot, E.; Bridel, M. Ann. Chim. Phys., 1913, 29, 145-218;
16. b) Vulfson, E.N.; Patel, R.; Beacher, J.E.; Andrews, A.T.; Low, B.A. Enzyme Microbial Technol., 1990, 12, 950-954;
17. c) Petit, J.M.; Paquet, F.; Beau, J.M. Tetrahedron Lett., 1991, 32, 6125-6128.
18. 5. a) Vic, G.; Thomas, D. Tetrahedron Lett., 1992, 33, 4567-4570;
19. b) Vic, G.; Crout, D.H.G. Tetrahedron: Asymmetry , 1994, 5, 2513-2516;
20. c) Vic, G.; Biton, J.; Le Beller, D.; Michel, J-M.; Thomas, D. Biotechnol. Bioeng., 1995, 46, 109-116.
21. 6. Vic, G.; Crout, D.H.G. Carbohydr. Res., 1995, 279, 315-319.
22. 7. Lindberg, A.A.; Brown, J.E.; Strömberg, N.; Westling-Ryd, M.; Shultz, J.E.; Karlsson, K-A. J. Biol. Chem. 1987, 262, 1779-1785.
23. 8. Lingwood, C.A.; Law, H.; Richardson, S.; Petric, H.; Brunton, J.L.; DeGrandis, S.; Karmoli, M. J. Biol. Chem., 1987, 262, 8834-8839.
24. 9. Leffler, H.; Svanborg-Eden, C. FEMS Microbiol. Lett., 1980, 8, 127-134.
25. 10. Valivety, R.H.; Hailing, P.J.; Macrae, A.R. Biochim. Biophys. Acta, 1992, 218-222.
26. 11. Vretblad, P. Biochim. Biophys. Acta, 1976, 434, 139-176.
27. 12. Janson, J-C. Trends Biotechnol., 1986, 2, 31-36.
28. 13. Fraser-Reid, B.; Udodong, U.E.; Wu, Z.; Ottosson, H.; Merritt, J.R.; Rao, C.S.; Roberts, C.; Madsen, R. Synlett, 1992, 12, 927-942.
29. 14. Lipshutz, B.H.; Pegram, J.J.; Morey, M.C. Tetrahedron Lett., 1981, 22, 4603-4606.
30. 15. Jansson, K., Ahlfors, S., Frejd, T., Kihlberg, J., Magnusson, G. J. Org. Chem., 1988, 53, 5629-5647.
31. 16. Kannagi, R.; Levery, S.B.; Ishigami, F.; Hakomori, S., Shevinsky, L.H., Knowles, B.B., Solter, D. J. Biol. Chem., 1983, 258, 8934-8942.
32. 17. Nudelman, E.; Kannagi, R., Hakomori, S., Parsons, M., Lipinski, M., Wiels, J.E.; Fellous, M.; Tursz, T. Science, 1983, 220, 509-511.
33. 18. Nicolaou, K.C.; Caulfield, T.J.; Katoaka, H. Carbohydr. Res., 1990, 202, 177-191.
34. 19. Taubken, N.; Thiem, J. Synthesis, 1992, 517-518.
35. 20. Reist, E.J.; Spencer, R.R.; Calkins, D.F.; Baker, B.R.; Goodman, L.J. J. Org. Chem., 1965, 30, 2312-2317.