Tyrosine sulfation on a PSGL-1 glycopeptide influences the reactivity of glycosyltransferases responsible for synthesis of the attached O-glycan [16]

Journal of the American Chemical Society

Volumn 122, Issue 4, 2000, Pages 742-743

  Koeller, Kathryn M ^a   Smith, Mark E B ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCAN; GLYCOPEPTIDE; GLYCOSYLTRANSFERASE; P SELECTIN GLYCOPROTEIN LIGAND 1; PADGEM PROTEIN;

CHEMICAL REACTION; GLYCOSYLATION; LETTER; MOLECULAR RECOGNITION; REACTION ANALYSIS; SULFATION; SYNTHESIS;

EID: 0033980705     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993820o     Document Type: Letter

References (19)

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14. -)-OH in SPPS to give the sulfated glycopeptide were unsuccessful. Problems arose when attempts to remove tBu groups in the presence of the sulfate failed: (a) Yagami, T.; Shiwa, S.; Futaki, S.; Kitagawa, K. Chem. Pharm. Bull. 1993, 41, 376. (b) Kitagawa, K.; Futaki, S.; Yagami, T.; Sumi, S.; Inoue, K. Int. J. Peptide Protein Res. 1994, 43, 190.
15. -)- OH in SPPS to give the sulfated glycopeptide were unsuccessful. Problems arose when attempts to remove tBu groups in the presence of the sulfate failed: (a) Yagami, T.; Shiwa, S.; Futaki, S.; Kitagawa, K. Chem. Pharm. Bull. 1993, 41, 376. (b) Kitagawa, K.; Futaki, S.; Yagami, T.; Sumi, S.; Inoue, K. Int. J. Peptide Protein Res. 1994, 43, 190.
16. The workup procedure employed was previously used for the sulfation of carbohydrate hydroxyls: Sanders, W. J.; Manning, D. D.; Koeller, K. M.; Kiessling, L. L. Tetrahedron 1997, 53, 16391.
17. Marseigne, I.; Roy, P.; Dor, A.; Durieuz, C.; Pelaprat, D.; Reibaud, M.; Blanchard, J. C.; Roques, B. P. J. Med. Chem. 1989, 32, 445.
18. The 2-dimensional ROESY spectra of 8a and 8b show nearly identical overlap. For previous studies of the effect of tyrosine sulfation on peptide conformation see: (a) Durieux, C.; Belleney, J.; Lallemand, J.-Y.; Roques, B. P.; Fouraie-Zaluski, M.-C. Biochem. Biophys. Res. Commun. 1983, 114, 705. (b) Fournie-Zaluski, M.-C.; Belleney, J.; Lux, B.; Durieux, C.; Gerard, D.; Gacel, G.; Maigret, B.; Roques, B. P. Biochemistry 1986, 25, 3778.
19. The 2-dimensional ROESY spectra of 8a and 8b show nearly identical overlap. For previous studies of the effect of tyrosine sulfation on peptide conformation see: (a) Durieux, C.; Belleney, J.; Lallemand, J.-Y.; Roques, B. P.; Fouraie-Zaluski, M.-C. Biochem. Biophys. Res. Commun. 1983, 114, 705. (b) Fournie-Zaluski, M.-C.; Belleney, J.; Lux, B.; Durieux, C.; Gerard, D.; Gacel, G.; Maigret, B.; Roques, B. P. Biochemistry 1986, 25, 3778.