Solid-phase synthesis of core 2 O-linked glycopeptide and its enzymatic sialylation

Tetrahedron

Volumn 59, Issue 42, 2003, Pages 8415-8427

  Takano, Yutaka ^a   Kojima, Naoya ^a   Nakahara, Yuko ^a   Hojo, Hironobu ^a   Nakahara, Yoshiaki ^a  

^a TOKAI UNIVERSITY   (Japan)

Author keywords

Glycopeptide; Glycosylation; Sialyltransferase; Solid phase synthesis

Indexed keywords

ACETAMIDE DERIVATIVE; DISACCHARIDE; FLUORIDE; GLYCOPEPTIDE; POLYSACCHARIDE; SERINE; THREONINE;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; GLYCOSYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; SIALYLATION; SOLID; STEREOCHEMISTRY; SYNTHESIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0141643399     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.047     Document Type: Article

References (28)

1. Hojo H., Watabe J., Nakahara Y., Nakahara Y., Ito Y., Nabeshima K., Toole B.P. Tetrahedron Lett. 42:2001;3001-3004.
2. Hojo H., Haginoya E., Matsumoto Y., Nakahara Y., Nabeshima K., Toole B.P., Watanabe Y. Tetrahedron Lett. 44:2003;2961-2964.
3. (a) Nakahara Y., Nakahara Y., Ito Y., Ogawa T. Tetrahedron Lett. 38:1997;7211-7214
4. (b) Nakahara Y., Nakahara Y., Ito Y., Ogawa T. Carbohydr. Res. 309:1998;287-296.
5. Ando S., Nakahara Y., Ito Y., Ogawa T., Nakahara Y. Carbohydr. Res. 329:2000;773-780.
6. Ichiyanagi, T.; Takatani, M.; Sakamoto, K.; Nakahara, Y.; Ito, Y.; Hojo, H.; Nakahara, Y. Tetrahedron Lett. 2002, 43, 3297-3300.
7. Piller F., Piller V., Fox R.I., Fukuda M. J. Biol. Chem. 263:1988;15146-15150.
8. (a) Saitoh O., Piller F., Fox R.I., Fukuda M. Blood. 77:1991;1491-1499
9. (b) Brockhausen I., Kuhns W., Schachter H., Matta K.L., Sutherland D.R., Baker M.A. Cancer Res. 51:1991;1257-1263.
10. Lefebvre J.-C., Giordanengo V., Limouse M., Doglio A., Cucchiarini M., Monpoux F., Mariani R., Peyron J.-F. J. Exp. Med. 180:1994;1609-1617.
11. (a) Singh L., Nakahara Y., Ito Y., Nakahara Y. Tetrahedron Lett. 40:1999;3769-3772
12. (b) Singh L., Nakahara Y., Ito Y., Nakahara Y. Carbohydr. Res. 325:2000;132-142.
13. (a) Unverzagt C., Kunz H., Paulson J.C. J. Am. Chem. Soc. 112:1990;9308-9309
14. (b) Unverzagt C., Kelm S., Paulson J.C. Carbohydr. Res. 251:1994;285-301
15. (c) Unverzagt C. Tetrahedron Lett. 38:1997;5627-5630
16. (d) Ajisaka K., Miyasato M. Biosci. Biotechnol. Biochem. 64:2000;1743-1746
17. (e) Koeller K.M., Smith M.E.B., Huang R.-F., Wong C.-H. J. Am. Chem. Soc. 122:2000;4241-4242
18. (f) George S.K., Schwientek T., Holm B., Reis C.A., Clausen H., Kihlberg J. J. Am. Chem. Soc. 123:2001;11117-11125
19. (g) Bézay N., Dudziak G., Liese A., Kunz H. Angew. Chem., Int. Ed. 40:2001;2292-2295.
20. Schuster M., Wang P., Paulson J.C., Wong C.-H. J. Am. Chem. Soc. 116:1994;1135-1136.
21. Takano Y., Habiro M., Someya M., Hojo H., Nakahara Y. Tetrahedron Lett. 43:2002;8395-8399.
22. (a) Nakahara Y., Nakahara Y., Ogawa T. Carbohydr. Res. 292:1996;71-78
23. (b) Nakamura K., Ishii A., Ito Y., Nakahara Y. Tetrahedron. 55:1999;11253-11266.
24. Blatter G., Beau J.-M., Jacquinet J.-C. Carbohydr. Res. 260:1994;189-201.
25. Watabe J., Singh L., Nakahara Y., Ito Y., Hojo H., Nakahara Y. Biosci. Biotechnol. Biochem. 66:2002;1904-1914.
26. Suzuki K., Maeta T., Matsumoto T., Tsuchihashi G. Tetrahedron Lett. 29:1988;3567-3570.
27. Chan W.C., White P.D. Fmoc Solid Phase Peptide Synthesis. 2000;Oxford University, Oxford.
28. Tam J.P., Heath W.F., Merrifield R.B. J. Am. Chem. Soc. 108:1986;5242-5251.