The design and synthesis of a conformationally constrained trisaccharide for probing carbohydrate-protein interactions

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 2023-2026

  Navarre, N ^a   Van Oijen, A H ^a   Boons, G J ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

LECTIN; TRISACCHARIDE;

ARTICLE; CHEMICAL REACTION; CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; HYDROGEN BOND;

EID: 0031575835     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00223-2     Document Type: Article

References (22)

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3. 2. R.U. Lemieux, Chem. Soc. Rev., 1989, 18, 347; F.A. Quiocho, Pure Appl. Chem., 1989, 61, 1293.
4. 2. R.U. Lemieux, Chem. Soc. Rev., 1989, 18, 347; F.A. Quiocho, Pure Appl. Chem., 1989, 61, 1293.
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6. 3. J. Montreuil, Adv. Carbohydr. Chem. Biochem., 1980, 37 157; J.P. Carver, Pure Appl. Chem., 1993, 65, 763; S.W. Homans, S. Foster, Glycobiology, 1992, 2, 143; T. Peters, B. Meyer, R. Stuike-Prill, R. Somarjai, J.R. Brisson, Carbohydr. Res., 1993, 238, 49.
7. 3. J. Montreuil, Adv. Carbohydr. Chem. Biochem., 1980, 37 157; J.P. Carver, Pure Appl. Chem., 1993, 65, 763; S.W. Homans, S. Foster, Glycobiology, 1992, 2, 143; T. Peters, B. Meyer, R. Stuike-Prill, R. Somarjai, J.R. Brisson, Carbohydr. Res., 1993, 238, 49.
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12. 7. Conformational locked carbohydrate mimics have been prepared to determine the recognition conformations of the exocyclic hydroxymethyl group, see: R.U. Lemieux, T.C. Wong, H. Thongersen, Can. J. Chem., 1982, 60, 81; K. Bock, J.O. Duus, O. Hindsgaul, I. Lindl, Carbohydr. Res., 1992, 228 (1), 1.
13. 7. Conformational locked carbohydrate mimics have been prepared to determine the recognition conformations of the exocyclic hydroxymethyl group, see: R.U. Lemieux, T.C. Wong, H. Thongersen, Can. J. Chem., 1982, 60, 81; K. Bock, J.O. Duus, O. Hindsgaul, I. Lindl, Carbohydr. Res., 1992, 228 (1), 1.
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19. -1 were stored. The torsion angles of the pyranose-rings were maintained during energy minimization and conformational searches. All minimisations were carried out in vacuo. Twenty conformations were isolated when filtering on the torsion angle data found for the trisaccharide in the crystallographic complex, allowing ±10°, using the filter-option in MacroModel.
20. -1 were stored. The torsion angles of the pyranose-rings were maintained during energy minimization and conformational searches. All minimisations were carried out in vacuo. Twenty conformations were isolated when filtering on the torsion angle data found for the trisaccharide in the crystallographic complex, allowing ±10°, using the filter-option in MacroModel.
21. -1 were stored. The torsion angles of the pyranose-rings were maintained during energy minimization and conformational searches. All minimisations were carried out in vacuo. Twenty conformations were isolated when filtering on the torsion angle data found for the trisaccharide in the crystallographic complex, allowing ±10°, using the filter-option in MacroModel.
22. -1 were stored. The torsion angles of the pyranose-rings were maintained during energy minimization and conformational searches. All minimisations were carried out in vacuo. Twenty conformations were isolated when filtering on the torsion angle data found for the trisaccharide in the crystallographic complex, allowing ±10°, using the filter-option in MacroModel.