Synthesis of heterodisaccharide-containing peptides, fragments of actinoidin antibiotics

Abstract

Prototypes corresponding to glycopeptide fragments of actinoidin antibiotics have been synthesized using an L-acosaminyl-D-glucose-containing heterodisaccharide linked to 4-hydroxyphenylglycine as pivotal synthon. This latter compound has been obtained by coupling of a suitably protected D-glucopyranosyl bromide with the blocked amino acid, followed by selective deprotection of the glucopyranosyl moiety at C-2 and subsequent stereospecific attachment of the acosaminyl unit.

References

1. D. T. W. Chu, J. J. Plattner and L. Katz, J. Med. Chem., 1996, 39, 3853.
2. For a general review, see D. H. Williams, Nat. Prod. Rep., 1996, 13, 469.
3. C. M. Pearce and D. H. Williams, J. Chem. Soc., Perkin Trans. 2, 1995, 153.
4. D. L. Boger, R. M. Borzilleri, S. Nukui and R. T. Beresis, J. Org. Chem., 1997, 62, 4721; J. Zhu, Synlett, 1997, 133; D. L. Boger, R. M. Borzilleri and S. Nukui, J. Org. Chem., 1996, 61, 3561; A. V. R. Rao, M. K. Gurja, K. L. Reddy and A. S. Rao, Chem. Rev., 1995, 95, 2135.
5. J. Csanádi, F. Sztaricskai, G. Batta, Z. Dinya and R. Bognar, Carbohydr. Res., 1986, 147, 211.
6. X. Dong, F. Tillequin, C. Monneret, G. Horvath and F. Sztaricskai, Carbohydr. Res., 1992, 232, 107.
7. R. G. Dushin and S. J. Danishefsky, J. Am. Chem. Soc., 1992, 114, 3471.
8. D. H. Williams and J. P. Waltho, Biochem. Pharmacol., 1988, 37, 133; J. P. Mackay, U. Gerhard, D. A. Beauregard, R. A. Maplestone and D. H. Williams, J. Am. Chem. Soc., 1994, 116, 4573; J. P. Mackay, U. Gerhard, D. A. Beauregard, M. S. Westwell, M. S. Searle and D. H. Williams, ibid., 1994, 116, 4581.
9. H. B. Borén, G. Ekborg, K. Eklind, P. J. Garegg, A. Pilotti and C. G. S. Wahn, Acta Chem. Scand., 1973, 27, 2639.
10. J. Banoub, P. Boullanger, M. Poiter and G. Descotes, Tetrahedron Lett., 1986, 27, 4145.
11. M. Trumtel, P. Tavecchia, A. Veyrières and P. Sinay, Carbohydr. Res., 1989, 191, 29.
12. G. M. Bebault, G. G. S. Dutton and C. K. Warfield, Carbohydr. Res., 1974, 34, 174.
13. F. W. Lichtenthaler and T. Schneider-Adams, J. Org. Chem., 1994, 59, 6728.
14. D. Dess, H. K. Kleine, D. V. Weinberg, R. J. Kaufman and R. S. Sidhu, Synthesis, 1981, 883; H. K. Kleine, D. V. Weinberg, R. J. Kaufman and R. S. Sidhu, Carbohydr. Res., 1985, 142, 333.
15. B. Abbaci, J.-C. Florent and C. Monneret, Bull. Soc. Chim. Fr., 1989, 667.
16. Z. J. Kaminski, Synthesis, 1987, 917.
17. Y. Amino, K. Kawada, K. Toi, I. Kumashiro and K. Fukushima, Chem. Pharm. Bull., 1988, 36, 4426.
18. K. Inouye, I. M. Voynick, G. R. Delpierre and J. S. Fruton, Biochemistry, 1966, 5, 2473.
19. L. Crombie, D. Haigh, R. C. F. Jones and A. R. Mat-Zin, J. Chem. Soc., Perkin Trans. 1, 1993, 2047.