Mucin type glycopeptides: Synthesis of Core 2, Core 6 and F1-α building blocks and some unexpected reactions

Tetrahedron Letters

Volumn 38, Issue 1, 1997, Pages 45-48

  Dongxu, Qiu ^a   Koganty, R Rao ^a  

^a Biomira Inc   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; GLYCOPROTEIN SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0343052906     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02252-6     Document Type: Article

References (19)

1. (a) Strous, G. J.; Dekker, J. Crit. Rev. Biochem. Mol. Bol. 1992, 27, 57-92.
2. (b) Carraway, K. L. ans Hull, S. Glycobiology 1991, 1, 131-138.
3. Schachter, H.; Brockhausen, I. In: Glycoconjugates: Composition, Structure and Fuction; Allen, H. J.; Kisailus, E. C. Eds.; Marcel Dekker, Inc.: New York 1992, 263-332.
4. (a) Bhavanandan, V. P. Glycobiology 1991, 1, 493-503.
5. (b) Yamashita, Y.; Chung, Y. S.; Horie, R.; Sowa, M. J. Natl. Can. Inst. 1995, 87, 441-446
6. (c) Kurosaka, A. et al. J. Biol. Chem. 1983, 258, 11594-11598 Hull, S. R. et al. Cancer Commun. 1989, 1, 261-267
7. (d) Hull, S. R. et al. Cancer Commun. 1989, 1, 261-267
8. (a) Fung, P. Y. S. et al. Cancer Res. 1990, 50, 4308-4314
9. (b) MacLean, G. D.et al. Cancer Immunol. Immunother. 1993, 36, 215-222.
10. (c) MacLean, G. D.et al. Cancer Immunol. Immunother. 1993, 36, 215-222. Longenecker, B. M. and MacLean, G. D. The Immunologist 1993, 1, 89-93.
11. (d) Longenecker, B. M. and MacLean, G. D. The Immunologist 1993, 1, 89-93.
12. (a) Horie, R.; Hara, K.; Nakano, K. Carbohydr. Res. 1992, 230, C11-C15
13. (a) Horie, R.; Hara, K.; Nakano, K. Carbohydr. Res. 1992, 230, C11-C15 (b)Yamashita, Y. et al. Int. J. Cancer 1994, 58, 349-355.
14. Fukase, K. et al. Tetrahedron Lett. 1995, 36, 7455-7458.
15. (a) Yule, J. E. et al. Tetrahedron Lett. 1995, 36, 6839-6842
16. (a) Yule, J. E. et al. Tetrahedron Lett. 1995, 36, 6839-6842
17. Grundler, G. and Schmidt, R. R. Liebigs Ann. Chem. 1984, 1826-1847
18. 3); 40. δ=6.17 (d, 1H, J=3.5 Hz, H-1a), 5.86 (d, 1H, J=9.0Hz, NH), 5.64 (d, 1H, J=9.5Hz, NH), 5.48(s, 1H, CHPh), 5.37 (m, 2H, H-4a, H-4b), 5.25 (t, 1 H, J=10.0Hz, H-3c), 5.13 (dd, 1H, J=8.0, 10.5Hz, H-2b), 4.98 ( dd, 1H, J=3.5, 10.5 Hz, H-3b), 4.64 (d, 1H, J=8.0Hz, H-1b), 4.60 (d, 1H, J= 8.5Hz, H-1c), 2.18, 2.17, 2.14, 2.08, 2.07, 2.06, 2.01, 1.99, 1.96 (9s, 27H, 9Ac). 41. δ=6.18 (d, 1H, J=3.5Hz, H-1a), 5.72 (d, 1H, J=9.5 Hz, NH), 5.64 (d, 1H, J=9.0Hz, NH), 5.50 (dd, 1H. J=1.0, 3.0Hz, H-4), 5.40 (dd, 1H, J=3.0, 11.0Hz, H-3a), 5.35 (dd, 1H, J=1.0, 3.0Hz, H-4), 5.06-5.15(m, 2H), 4.96 (dd, 1H, J=3.5, 10.0Hz, H-3c), 4.88 (m, 1H, H-2a), 4.57 (d, 1H, J=7.5Hz, H-1b), 4.48 (d, 1H, J=7.5Hz, H-1c), 2.22, 2.18, 2.16, 2.12, 2.07, 2.05, 2.04, 1.97, 1.89 (9s, 30H, 10Ac).
19. Meinjohanns, E. et al. J. Chem. Soc., Perkin Trans. 1 1996, 985-993.