Stereoselective enzymatic galactosylation of C-glucosides

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Luigi Panza, Pietro L. Chiappini, Giovanni Russo, Daniela Monti and Sergio Riva


Abstract

The enzyme β-1,4-galactosyl transferase from bovine colostrum (GalT) is able stereoselectively to galactosylate C-glucosides (i.e. 1 and 4), precursors of stable glycoconjugate analogues, and a systematic investigation of the structural modifications at C-1 and/or C-5 of the glycosides that can be accepted by this enzyme has been undertaken, adding information to the currently accepted model of substrate binding into the GalT active site.


References

  1. C. Bertozzi and M. Bednarsky, in Modern Methods in Carbohydrate Synthesis, ed. S. H. Khan and R. A. O'Neill, Harwood Academic Publisher, Amsterdam, NL, 1996, p. 316 Search PubMed.
  2. (a) G. Carrea, G. Ottolina and S. Riva, Trends Biotechnol., 1995, 13, 63 CrossRef CAS; (b) B. Danieli and S. Riva, Pure Appl. Chem., 1994, 66, 2215 CAS; (c) K. Faber and S. Riva, Synthesis, 1992, 895 CrossRef CAS; (d) L. Panza, S. Brasca, S. Riva and G. Russo, Tetrahedron: Asymmetry, 1993, 4, 931 CrossRef CAS; (e) L. Panza, M. Luisetti, E. Crociati and S. Riva, J. Carbohydr. Chem., 1993, 12, 125 CAS; (f) S. Riva, J. Chopineau, A. P. G. Kieboom and A. M. Klibanov, J. Am. Chem. Soc., 1988, 110, 584 CrossRef CAS.
  3. D. Monti, E. Giosuè, S. Riva and L. Panza, Gazz. Chim. Ital., 1996, 126, 303 CAS.
  4. (a) C.-H. Wong, L. R. Halcomb, Y. Ichikawa and T. Kajimoto, Angew. Chem., 1995, 107, 521; Angew. Chem., Int. Ed. Engl., 1995, 34, 521 Search PubMed; (b) M. M. Palcic, O. P. Srivastava and O. Hindsgaul, Carbohydr. Res., 1987, 159, 315 CrossRef CAS; (c) C. Augè, S. David, C. Mathieu and C. Gautheron, Tetrahedron Lett., 1984, 25, 1467 CrossRef CAS.
  5. T. V. RajanBabu and G. S. Reddy, J. Org. Chem., 1986, 51, 5458 CrossRef CAS.
  6. (a) L. J. Berliner, M. E. Davis, K. E. Ebner, T. A. Beyer and E. Bell, Mol. Cell. Biochem., 1984, 62, 37 CrossRef CAS; (b) C.-H. Wong, Y. Ichikawa, T. Krach, C. Gautheron-Le Narvor, P. D. Dumas and G. C. Look, J. Am. Chem. Soc., 1991, 113, 8137 CrossRef CAS.
  7. Compound 14 was obtained according to L. Lay, F. Nicotra, L. Panza and G. Russo, Synlett, 1995, 167 Search PubMed.
  8. Hindsgaul also observed an inhibitive action of an aminosugar acceptor with a different galactosyl transferase: T. L. Lowary and O. Hindsgaul, Carbohydr. Res., 1994, 251, 33 Search PubMed.
  9. Selected NMR data: benzoylated 1a: δH(CDCl3, J/Hz) 5.58 (t, J9.7, 1 H, H-3), 4.88 (d, J7.8, 1 H, H-1′), 4.22 (dd app. as t, J9.5, 1 H, H-5), 4.03 (m, 1 H, H-2); benzoylated 2a: δH(CDCl3) 5.57 (dd app. as t, J 9.7, 1 H, H-3), 4.88 (d, J8.0, 1 H, H-1′), 4.22 (dd app. as t, J9.4, 1 H, H-5); benzoylated 4a: δH(CDCl3) 4.88 (d, J8.0, 1 H, H-1′), 4.20 (dd app. as t, J 9.4, 1 H, H-5); 1a: δC(D2O) 103.2, 79.5, 79.0, 78.6, 76.2, 75.7, 72.9, 71.3, 69.9, 68.9, 61.4 (2C), 60.8; 2a: δC(D2O) 103.3, 79.0, 78.5, 76.3, 75.7, 72.9, 71.3, 69.8, 68.9, 61.4 (2C), 60.8; 4a: δC(D2O) 159.4, 137.4, 129.7 (2C), 129.3, 128.6 (2C), 103.8, 79.5, 79.1, 78.7, 76.6, 76.2, 73.5, 71.9, 71.6, 69.5, 68.1, 67.9, 61.9, 61.3, 42.4; 5a: δC(D2O) 103.7, 79.9, 79.5, 76.9, 76.2, 73.4, 71.8, 69.9, 69.5, 69.3, 61.8, 61.1.
  10. C.-H. Wong, P. Schuster, P. Wang and P. Sears, J. Am. Chem. Soc., 1993, 115, 5893 CrossRef CAS.
  11. T. Wiemann, Y. Nishida, V. Sinnwell and J. Thiem, J. Org. Chem., 1994, 59, 6744 CrossRef CAS.
  12. L. Yu, R. Cabrera, J. Ramirez, V. A. Malinovskii, K. Brew and P. G. Wang, Tetrahedron Lett., 1995, 36, 2897 CrossRef CAS.
  13. (a) E. A. Davidson, Biochim. Biophys. Acta, 1959, 33, 238 CrossRef CAS; (b) D. K. Fitzgerald, B. Colvin, R. Mawal and K. E. Ebner, Anal. Biochem., 1970, 43 CrossRef CAS.
  14. (a) M. Schultz and H. Kunz, Tetrahedron Lett., 1992, 33, 5319 CrossRef CAS; (b) J. Thiem and T. Wiemann, Angew. Chem., 1990, 102, 78 CAS; Angew. Chem., Int. Ed. Engl., 1990, 29, 80 Search PubMed; (c) C. Unverzagt, H. Kunz and J. J. Paulson, J. Am. Chem. Soc., 1990, 112, 9308 CrossRef CAS.
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