Syntheses of α-dystroglycan derived sialylated glycosyl amino acids carrying a novel mannosyl serine/threonine linkage

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6803-6807

  Seifert, Joachim ^a   Ogawa, Tomoya ^a   Ito, Yukishige ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Amino acid derivatives; Amino acids; Glycopeptides; Glycoproteins; Glycosidation

Indexed keywords

AMINO ACID; AMINO ACID DERIVATIVE; CARBOHYDRATE; DYSTROGLYCAN; GLYCOPEPTIDE; GLYCOPROTEIN; LAMININ BINDING PROTEIN; MONOSACCHARIDE; SERINE DERIVATIVE; THREONINE;

ARTICLE; CHEMICAL REACTION; CROSS LINKING; REACTION ANALYSIS; SEQUENCE ANALYSIS; SYNTHESIS;

EID: 0033543630     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01361-1     Document Type: Article

References (26)

1. (a) Chiba, A.; Matsumura, K.; Yamada, H.; Inazu, T.; Shimizu, T.; Kusunoki, S.; Kanazawa, I.; Kobata, A.; Endo, T. J. Biol. Chem. 1997, 272, 2156-2162, and references cited therein.
2. (b) Matsumura, K.; Chiba, A.; Yamada, H.; Fukuta-Ohi, H.; Fujita, S.; Endo, T.; Kobata, A.; Anderson, L. V. B.; Kanazawa, I.; Campbell, K. P.; Shimizu, T. ibid. 1997, 272, 13904-13910.
3. (c) Ibraghimov-Beskrovnaya, O.; Ervasti, J. M.; Leveille, C. J.; Slaughter, C. A.; Sernett, S. W.; Campbell, K. P. Nature 1992, 355, 696-702, and references cited therein.
4. (d) Campbell, K. P. Cell 1995, 80, 675-679.
5. (e) The stereochemistry of the O-mannosyl serine/threonine linkage is not confirmed.
6. (a) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235.
7. (b) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
8. 19a: Schultz, M.; Kunz, H. Tetrahedron: Asymmetry 1993, 4, 1205-1220.
9. 19b: Green, M.; Berman, J. Tetrahedron Lett. 1990, 31, 5851-5852.
10. 19c,d: (a) de la Torre, B. G.; Torres, J. L.; Bardaji, E.; Clapes, P.; Xaus, N.; Jorba, X.; Calvet, S.; Albericio, F.; Valentia, G. J. Chem. Soc., Chem. Commun. 1990, 965-967.
11. (b) Ciommer, M.; Kunz, H. Synlett 1991, 593-595.
12. (a) Veeneman, G. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 275-278.
13. (b) Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331-1334.
14. (c) Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313-4316.
15. (d) Nagahama, T.; Ohki, H.; Hotta, K.; Ishida, H.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1991, 10, 493-498.
16. 4×HOAc, DMF, 0°C (85%); (ii) TDMSCl, imidazole, DMF, 0°C-rt (91%); (iii) NaOMe/MeOH, -10°C (93%); for the use of the TDMS group for anomeric protection, see (c).
17. (b) Dekany, G.; Wright, K.; Toth, I. J. Carbohydr. Chem. 1997, 16, 983-999.
18. (c) Hummel, G.; Schmidt, R. R. Tetrahedron Lett. 1997, 38, 1173-1176.
19. Guenther, W.; Kunz, H. Carbohydr. Res. 1992, 228, 217-241.
20. (a) Franks, N. E.; Montgomery, R. Carbohydr. Res. 1968, 6, 286-298.
21. (b) Ogawa, T.; Beppu, K.; Nakabayashi, S. ibid. 1981, 93, C6-C9.
22. Kanie, O.; Crawley, S. C.; Palcic, M. M.; Hindsgaul, O. Carbohydr. Res. 1993, 243, 139-164.
23. Vasella, A.; Witzig, C.; Chiara, J. L.; Martin-Lomas, M. Helv. Chim. Acta 1991, 74, 2073-2077.
24. Baylay, H.; Standring, D. N.; Knowles, J. R. Tetrahedron Lett. 1978, 39, 3633-3634.
25. SA).
26. 2O). 1a was recently synthesized chemoenzymatically by Matsuo, I.; Isomura, M.; Ajisaka, K. Tetrahedron Lett. 1999, 40, 5047-5050.