Stereoselective syntheses of phosphorylated and sulfated glycosyl serines in glycosaminoglycan for biological probes

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 14, 1999, Pages 1911-1914

  Tamura, Jun ichi ^a   Nishihara, Junko ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSYLSERINE; GLYCOSAMINOGLYCAN; N ACETYLGLUCOSAMINE; OLIGOSACCHARIDE; SERINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG STRUCTURE; PHOSPHORYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; SULFATION; SYNTHESIS;

DISACCHARIDES; GLYCOCONJUGATES; GLYCOSAMINOGLYCANS; MOLECULAR PROBES; MONOSACCHARIDES; PHOSPHORYLATION; SERINE; STEREOISOMERISM; SULFATES;

EID: 0033584189     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00300-5     Document Type: Article

References (18)

1. Sugahara, K.; Ohi, Y.; Harada, T.; de Waard, P.; Vliegenthart, J. F. G. J. Biol. Chem. 1992, 267, 6027. de Waard, P.; Vliegenthart, J. F. G.; Harada, T.; Sugahara, K. ibid. 1992, 267, 6036. Kitagawa, H.; Oyama, M.; Masayama, K.; Yamaguchi, Y.; Sugahara, K. Glycobiology 1997, 7, 1175.
2. Sugahara, K.; Ohi, Y.; Harada, T.; de Waard, P.; Vliegenthart, J. F. G. J. Biol. Chem. 1992, 267, 6027. de Waard, P.; Vliegenthart, J. F. G.; Harada, T.; Sugahara, K. ibid. 1992, 267, 6036. Kitagawa, H.; Oyama, M.; Masayama, K.; Yamaguchi, Y.; Sugahara, K. Glycobiology 1997, 7, 1175.
3. Sugahara, K.; Ohi, Y.; Harada, T.; de Waard, P.; Vliegenthart, J. F. G. J. Biol. Chem. 1992, 267, 6027. de Waard, P.; Vliegenthart, J. F. G.; Harada, T.; Sugahara, K. ibid. 1992, 267, 6036. Kitagawa, H.; Oyama, M.; Masayama, K.; Yamaguchi, Y.; Sugahara, K. Glycobiology 1997, 7, 1175.
4. Fransson, L.-Å.; Silverberg, I.; Carlstedt, I. J. Biol. Chem. 1985, 260, 14722. Rosenfeldt, L.; Danishefsky, I. ibid. 1988, 263, 262.
5. Fransson, L.-Å.; Silverberg, I.; Carlstedt, I. J. Biol. Chem. 1985, 260, 14722. Rosenfeldt, L.; Danishefsky, I. ibid. 1988, 263, 262.
6. Oegema, Jr., T. R.; Kraft, E. L.; Jourdian, G. W.; Van Valen, T. R. ibid. 1984, 259, 1720.
7. Esko, J. D.; Zhang, L. Curr. Opin. Struct. Biol. 1996, 6, 663. Brinkmann, T; Weilke, C.; Kleesiek, K. J. Biol. Chem. 1997, 272, 11171.
8. Esko, J. D.; Zhang, L. Curr. Opin. Struct. Biol. 1996, 6, 663. Brinkmann, T; Weilke, C.; Kleesiek, K. J. Biol. Chem. 1997, 272, 11171.
9. Moses, J.; Oldberg, Å.; Cheng, F.; Fransson, L.-Å. Eur. J. Biochem. 1997, 248, 521.
10. Goto, F.; Ogawa, T. Tetrahedron Lett. 1992, 33, 5099, 6841. Idem. Pure Appl. Chem. 1993, 4, 793.
11. Goto, F.; Ogawa, T. Tetrahedron Lett. 1992, 33, 5099, 6841. Idem. Pure Appl. Chem. 1993, 4, 793.
12. Nilsson, M.; Westman, J.; Svahn, C.-M. J. Carbohydr. Chem. 1993, 12, 23.
13. Rio, S.; Beau, J.-M; Jacquinet, J.-C. Carbohydr. Res. 1994, 255, 103.
14. Ono, N.; Yamada, T.; Saito, T.; Tanaka, K.; Kaji, A. Bull. Chem. Soc. Jpn. 1978, 51, 2401.
15. Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1991, 32, 1569.
16. Sterically hindered pivaloyl group was introduced only at O-3 of 13 in 82 %.
17. -.
18. It was difficult to identify by mass spectrum whether all the acidic groups were converted to sodium salt.