Chemical synthesis of GDP-L-galactose and analogues

Carbohydrate Research

Volumn 306, Issue 3, 1998, Pages 409-419

  Binch, Hayley ^a   Stangier, Katja ^a   Thiem, Joachim ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

3,6 Dideoxy L galactose; 3 Deoxy L galactose; GDP L galactose and analogues; L Galactono 1,4 1actone

Indexed keywords

3 DEOXY LEVO GALACTOSE; 3,6 DEOXY LEVO GALACTOSE; GALACTITOL; GALACTOSE; GUANOSINE DIPHOSPHATE SUGAR; LEVO FUCOSE; LEVO GALACTONO 1,4 LACTONE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0031800609     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(97)10094-5     Document Type: Article

References (27)

1. [1] T.W. Rademacher, R.B. Parekh, and R.A. Dwek, Annu. Rev. Biochem., 1988, 57, 785-838; R.U. Lemieux, Chem. Soc. Rev., 1989, 18, 347-374.
2. [1] T.W. Rademacher, R.B. Parekh, and R.A. Dwek, Annu. Rev. Biochem., 1988, 57, 785-838; R.U. Lemieux, Chem. Soc. Rev., 1989, 18, 347-374.
3. [2] (a) T.K. Lindhorst and J. Thiem, Carbohydr. Res., 1991, 209, 119-129;
4. (b) B. Leon, T.K. Lindhorst, A. Rieks-Everdiking and W. Klaffke, Synthesis, 1994, 689-691.
5. [3] R. Stiller and J. Thiem, Liebigs Ann. Chem., 1992, 467-471; V. Ginsburg, J. Biol. Chem., 1960, 235, 2196-2201; V. Ginsburg, J. Biol. Chem., 1961, 236, 2389-2393; H. Ishihara, D.J. Massaro, and B.C. Heath, J. Biol. Chem., 1968, 243, 1103-1109; I. Jabbal and H. Schachter, J. Biol. Chem., 1971, 246, 5154-5161; H. Schachter, H. Ishihara, and E.C. Heath, Methods Enzymol., 1972, 28, 285-287.
6. [3] R. Stiller and J. Thiem, Liebigs Ann. Chem., 1992, 467-471; V. Ginsburg, J. Biol. Chem., 1960, 235, 2196-2201; V. Ginsburg, J. Biol. Chem., 1961, 236, 2389-2393; H. Ishihara, D.J. Massaro, and B.C. Heath, J. Biol. Chem., 1968, 243, 1103-1109; I. Jabbal and H. Schachter, J. Biol. Chem., 1971, 246, 5154-5161; H. Schachter, H. Ishihara, and E.C. Heath, Methods Enzymol., 1972, 28, 285-287.
7. [3] R. Stiller and J. Thiem, Liebigs Ann. Chem., 1992, 467-471; V. Ginsburg, J. Biol. Chem., 1960, 235, 2196-2201; V. Ginsburg, J. Biol. Chem., 1961, 236, 2389-2393; H. Ishihara, D.J. Massaro, and B.C. Heath, J. Biol. Chem., 1968, 243, 1103-1109; I. Jabbal and H. Schachter, J. Biol. Chem., 1971, 246, 5154-5161; H. Schachter, H. Ishihara, and E.C. Heath, Methods Enzymol., 1972, 28, 285-287.
8. [3] R. Stiller and J. Thiem, Liebigs Ann. Chem., 1992, 467-471; V. Ginsburg, J. Biol. Chem., 1960, 235, 2196-2201; V. Ginsburg, J. Biol. Chem., 1961, 236, 2389-2393; H. Ishihara, D.J. Massaro, and B.C. Heath, J. Biol. Chem., 1968, 243, 1103-1109; I. Jabbal and H. Schachter, J. Biol. Chem., 1971, 246, 5154-5161; H. Schachter, H. Ishihara, and E.C. Heath, Methods Enzymol., 1972, 28, 285-287.
9. [3] R. Stiller and J. Thiem, Liebigs Ann. Chem., 1992, 467-471; V. Ginsburg, J. Biol. Chem., 1960, 235, 2196-2201; V. Ginsburg, J. Biol. Chem., 1961, 236, 2389-2393; H. Ishihara, D.J. Massaro, and B.C. Heath, J. Biol. Chem., 1968, 243, 1103-1109; I. Jabbal and H. Schachter, J. Biol. Chem., 1971, 246, 5154-5161; H. Schachter, H. Ishihara, and E.C. Heath, Methods Enzymol., 1972, 28, 285-287.
10. [3] R. Stiller and J. Thiem, Liebigs Ann. Chem., 1992, 467-471; V. Ginsburg, J. Biol. Chem., 1960, 235, 2196-2201; V. Ginsburg, J. Biol. Chem., 1961, 236, 2389-2393; H. Ishihara, D.J. Massaro, and B.C. Heath, J. Biol. Chem., 1968, 243, 1103-1109; I. Jabbal and H. Schachter, J. Biol. Chem., 1971, 246, 5154-5161; H. Schachter, H. Ishihara, and E.C. Heath, Methods Enzymol., 1972, 28, 285-287.
11. [4] (a) H.A. Nunez, J.V. OÿConnor, P.R. Rosevear, and R. Barker, Can. J. Chem., 1981,59, 2086-2095;
12. (b) P. Westerduin, G.H. Veeneman, J.E. Marugg, G.A. van der Mare, and J.H. van Boom, Tetrahedron Lett., 1986, 27, 1211-1214;
13. (c) R.R. Schmidt, B. Wegmann, and K.H. Jung, Liebigs Ann. Chem., 1991, 121-124;
14. (d) U.B. Gokhale, O. Hindsgaul, and M.M. Palcic, Can. J. Chem., 1990, 68, 1063-1071;
15. (e) K. Adelhorst and G.M. Whitesides, Carbohydr. Res., 1993, 242, 69-76;
16. (f) B.M. Heskamp, H.J.G. Broxterman, G.A. van der Marel, and J.H. van Boom, J. Carbohydr. Chem., 1996, 15, 611-622.
17. [5] (a) T. K. Lindhorst and J. Thiem, Liebigs Ann. Chem., 1990, 1237-1241;
18. (b) D. Horton, T.M. Cheung and W. Weckerle, Methods Carbohydr. Chem., 1980, 8, 201-205.
19. [6] H.L. Frush and H.S. Isbell, Methods Carbohydr. Chem., 1962, 1, 127-130.
20. [7] K. Bock, I. Lundt, and C. Pedersen, Carbohydr. Res., 1981, 90, 7-16.
21. [8] O.J. Varela, A. Fernández-Cirelli, and R.M. De Lederkremer, Carbohydr. Res., 1980, 79, 219-224.
22. [9] K. Bock, I. Lundt, and C. Pedersen, Acta Chem. Scand., 1981, 35B, 155-162.
23. [10] (a) P. Kohn, L.M. Lerner, A. Chan, S.D. Ginocchio, and C.A. Zitrin, Carbohydr. Res., 1968, 7, 21-26;
24. (b) C. Pedersen and H.S. Jensen, Acta Chem. Scand., 1994, 48, 222-227.
25. [11] C. Pedersen, K. Bock, and I. Lundt, Pure Appl. Chem., 1978, 50, 1385-1400.
26. [12] K. Bock, I. Lundt, and C. Pedersen, Carbohydr. Res., 1979, 68, 313-319.
27. [13] V. Wittmann and C.H. Wong, J. Org. Chem., 1997, 62, 2144-2147.