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For alternative synthetic strategies to polyvalent carbohydrate-substituted materials, see: (a) Schnarr, R. L.; Weigel, P. H.; Kuhlenschmidt, M. S.; Lee, Y. C.. Roseman, S. J. Biol. Chem. 1979, 253, 7940-51. (b) Kingery-Wood. J. E.; Williams, K. W.; Sigal. G. B., Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 7303-5. (c) Roy, R.; Zanini. D.; Meunier, S. J.; Romanowska. A. J. Chem. Soc.. Chem. Commun. 1993, 1869-72. (d) Spevak, W.; Nasy, J. O.; Charych, D. H.; Schaefer, M. E.; Gilbert, J. H.; Bednarski, M. D. J. Am. Chem. Soc. 1993, 115, 1146-7. (e) Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71-77 and references cited therein.
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For alternative synthetic strategies to polyvalent carbohydrate-substituted materials, see: (a) Schnarr, R. L.; Weigel, P. H.; Kuhlenschmidt, M. S.; Lee, Y. C.. Roseman, S. J. Biol. Chem. 1979, 253, 7940-51. (b) Kingery-Wood. J. E.; Williams, K. W.; Sigal. G. B., Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 7303-5. (c) Roy, R.; Zanini. D.; Meunier, S. J.; Romanowska. A. J. Chem. Soc.. Chem. Commun. 1993, 1869-72. (d) Spevak, W.; Nasy, J. O.; Charych, D. H.; Schaefer, M. E.; Gilbert, J. H.; Bednarski, M. D. J. Am. Chem. Soc. 1993, 115, 1146-7. (e) Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71-77 and references cited therein.
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For alternative synthetic strategies to polyvalent carbohydrate-substituted materials, see: (a) Schnarr, R. L.; Weigel, P. H.; Kuhlenschmidt, M. S.; Lee, Y. C.. Roseman, S. J. Biol. Chem. 1979, 253, 7940-51. (b) Kingery-Wood. J. E.; Williams, K. W.; Sigal. G. B., Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 7303-5. (c) Roy, R.; Zanini. D.; Meunier, S. J.; Romanowska. A. J. Chem. Soc.. Chem. Commun. 1993, 1869-72. (d) Spevak, W.; Nasy, J. O.; Charych, D. H.; Schaefer, M. E.; Gilbert, J. H.; Bednarski, M. D. J. Am. Chem. Soc. 1993, 115, 1146-7. (e) Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71-77 and references cited therein.
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and references cited therein
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For alternative synthetic strategies to polyvalent carbohydrate-substituted materials, see: (a) Schnarr, R. L.; Weigel, P. H.; Kuhlenschmidt, M. S.; Lee, Y. C.. Roseman, S. J. Biol. Chem. 1979, 253, 7940-51. (b) Kingery-Wood. J. E.; Williams, K. W.; Sigal. G. B., Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 7303-5. (c) Roy, R.; Zanini. D.; Meunier, S. J.; Romanowska. A. J. Chem. Soc.. Chem. Commun. 1993, 1869-72. (d) Spevak, W.; Nasy, J. O.; Charych, D. H.; Schaefer, M. E.; Gilbert, J. H.; Bednarski, M. D. J. Am. Chem. Soc. 1993, 115, 1146-7. (e) Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71-77 and references cited therein.
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For a study of naturally-occurrina polyvalent saccharides, see: Mandal, D. K.; Brewer, C. F. Biochemistry 1993, 32, 5116-20.
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21
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13344282614
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note
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For experimental details, see the supporting information.
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23
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13344281949
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note
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These improvements in efficacy result from the multivalent presentation of the ligands and are not a nonspecific effect of the polymer chain. A structurally related neoglycopolymer bearing a sugar not bound by concanavalin A. fucose. did not inhibit agglutination, ref 6.
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24
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0019407381
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These effects can be analyzed in the context of the chelate effect: see: Jencks, W. P. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 4046-50.
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Jencks, W.P.1
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