Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

4-Deoxy-Analogs of p-Nitrophenyl $\beta$-D-Galactopyranosides for Specificity Study with $\beta$-Galactosidase from Escherichia coli

  • Published : 1996.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

The synthesis is reported of p-nitrophenyl glycosides of D-galactose modified at C-4 with azido- (5), amino- (6) group and fluorine (13). 4-Azido-2,3,6-tri-O-benzoyl-4-deoxy-α-D-galactopyranosyl chloride and 2,3,6-tri-O-benzoyl-4-deoxy-4-fluoro-α-D-galactopyranosyl bromide were coupled with potassium p-nitrophenoxide in the presence of 18-crown-6 giving the corresponding p-nitrophenyl 4-azido-and 4-fluoro-4-deoxy-β-D-galactopyranoside derivatives. p-Nitrophenyl 4-amino-4-deoxy-β-D-galactopyranoside (6) was obtained by selective reduction of p-nitrophenyl 4-azido-4-deoxy-β-D-galactopyranoside (5) using 1,3-propane dithioltriethylamine. These galactoside analogs were slowly hydrolyzed in the increasing rate order of 5, 6 and 13 by β-galactosidase from Escherichia coli.

Keywords

References

  1. Science v.154 Monod, J.
  2. Advan. in Carbohydr. Chem. and Biochem. v.16 Wallenfels, K.;Malhotra, O. P.
  3. Carbohydr. Res. v.158 John, C.;Lehmann, J.;Littke, W.
  4. Can. J. Biochem. v.60 Huber, R. E.;Gaunt, M. T.
  5. Carbohydr. Res. v.116 Legler, G.;Herrchen, M.
  6. J. Am. Chem. Soc. v.109 Withers, S. G.;Street, I. P.;Bird, P.;Dolphin, D. H.
  7. J. Biol. Chem. v.263 Withers, S. G.;Rupitz, K.;Street, I. P.
  8. J. Biol. Chem. v.265 Cupples, C. G.;Miller, J. H.;Huber, R. E.
  9. Biochem. Biophys. Res. Commun. v.171 Edwards, R. A.;Cupples, C. G.;Huber R. E.
  10. J. Biol. Chem. v.267 Gebler, J. C.;Aebersold, R.;Withers, S. G.
  11. Carbohydr. Res. v.84 Nam, S. J. E.;Maradufu, A.;Marrion, J.;Perlin, A. S.
  12. Carbohydr. Res. v.32 Maradufu, A.;Perlin, A. S.
  13. Carbohydr. Res. v.32 Maradufu, A.;Perlin, A. S.
  14. J. Org. Chem. v.39 Lichtenthaler, F. W.;Heidel, P.
  15. Carbohydr. Res. v.175 Thomas, R. L.;Abbas, S. A.;Piskorz, C. F.;Matta, K. L.
  16. Chem. Rev. v.91 Glaudemans, C. P. J.
  17. Chem. Rev. v.92 Banoub, J.;Boullanger, P.;Lafont, D.
  18. Carbohydr. Res. v.256 Lowary, T. L.;Swiedler, S. J.;Hindsgaul, O.
  19. J. Carbohydr. Res. v.259 Mulard, L. A.; Kovac, P.;Glaudemans, C. P.
  20. J. Carbohydr. Res. v.259 Mulard, L. A.; Kovac, P.;Glaudemans, C. P.
  21. Biochem. J. v.115 Dey, P. M.;Pridham, J. B.
  22. Carbohydr. Res. v.162 Eschenfelder, V.;Brossmer, R.
  23. Carbohydr. Res. v.220 Jain, R. K.;Sarkar, A. K.;Matta, K. L.
  24. J. Carbohydr. Res. v.134 Ekborg, G.;Glaudemans, C. P.
  25. Bull. Korean Chem. Soc. v.15 Yoon, S.;Kim, D.;Nam, S. J. E.
  26. J. Carbohydr. Chem. v.6 Shah, R. N.;Baptista, J.;Perdomo, G. R.;Carver, J. P.;Krepinsky, J. J.
  27. Carbohydr. Res. v.73 Eby, R.;Sondheimer, S. J.;Schuerch, C.
  28. Methods in Carbohydrate Chemistry v.2 Lemieux, R. U.;Whistler, R. L.(ed.);Wolfrom, M. L.(ed.)
  29. Chem. Ber. v.114 Paulsen, H.;Schnell, D.
  30. J. Org. Chem. v.44 Belinka, Jr. B. A.;Hassner, A.
  31. J. Carbohydr. Chem. v.8 Ito, Y.;Kiso, M.;Hasegawa, A.
  32. Tetrahedron Lett. Bayley, H.;Standring, D. N.;Knowles, J. R.
  33. Soong Sil University, MSc. thesis Yoon, S.
  34. J. Org. Chem. v.48 Card, P. J.;Reddy, G. S.
  35. J. Carbohydr. Chem. v.3 Kovac, P.;Glaudemans, C. P. J.
  36. J. Carbohydr. Chem. v.4 Card, P. J.
  37. Can. J. Chem. v.65 Doboszewski, B.;Hay, G. W.;Szarek, W. A.
  38. The Nature of the Chemical Bond(3rd Ed.) Pauling, L.
  39. J. Biol. Chem. v.253 Deschavanne, P. J.;Viratelle, O. M.;Yon, J. M.