Synthesis of the C-disaccharide α-C(1→3)-L-fucopyranoside of N-acetylgalactosamine

Journal of Carbohydrate Chemistry

Volumn 20, Issue 7-8, 2001, Pages 733-746

  Viodé, Cécile ^a,b   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035527805     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-100108286     Document Type: Article

References (46)

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2. Vogel, P. Monosacharide and Disaccharide Mimics: New Molecular Tools for Biology and Medicine. Chimia 2001, 55, 359-365 and ref. cited therein. Feizi, T. Oligosaccharides that mediate mammalian cell-cell adhesion. Curr. Opin. Struct. Biol. 1993, 3, 701-710. Bradley, S. J.; Fazli, A.; Kiefel, M. J.; Itzstein, M. Syntheis of Novel Sialylmimetics as Biological Probes. Bioorg. Med. Chem. Lett. 2001, 11, 1587-1590. Lindhorst, T. K. Structure and function of carbohydrates. Naturwiss. Unterr. Chem. 2001, 12, 9-12. Johns, B. A.; Pau, Y. T.; Elbein, A. D. Johnson, C. R. Synthesis and Biological Evaluation of Aza-C-disaccharides: (1→6), (1→4) and (1→1) Linked Sugar Mimics. J. Am. Chem. Soc. 1997, 119, 4856-4865. Musser, J. H.; Anderson, M. B.; Levy, D. E. Glycomimetics as selectin inhibitors. Curr. Pharm. Des. 1995, 1, 221-232.
3. Vogel, P. Monosacharide and Disaccharide Mimics: New Molecular Tools for Biology and Medicine. Chimia 2001, 55, 359-365 and ref. cited therein. Feizi, T. Oligosaccharides that mediate mammalian cell-cell adhesion. Curr. Opin. Struct. Biol. 1993, 3, 701-710. Bradley, S. J.; Fazli, A.; Kiefel, M. J.; Itzstein, M. Syntheis of Novel Sialylmimetics as Biological Probes. Bioorg. Med. Chem. Lett. 2001, 11, 1587-1590. Lindhorst, T. K. Structure and function of carbohydrates. Naturwiss. Unterr. Chem. 2001, 12, 9-12. Johns, B. A.; Pau, Y. T.; Elbein, A. D. Johnson, C. R. Synthesis and Biological Evaluation of Aza-C-disaccharides: (1→6), (1→4) and (1→1) Linked Sugar Mimics. J. Am. Chem. Soc. 1997, 119, 4856-4865. Musser, J. H.; Anderson, M. B.; Levy, D. E. Glycomimetics as selectin inhibitors. Curr. Pharm. Des. 1995, 1, 221-232.
4. Vogel, P. Monosacharide and Disaccharide Mimics: New Molecular Tools for Biology and Medicine. Chimia 2001, 55, 359-365 and ref. cited therein. Feizi, T. Oligosaccharides that mediate mammalian cell-cell adhesion. Curr. Opin. Struct. Biol. 1993, 3, 701-710. Bradley, S. J.; Fazli, A.; Kiefel, M. J.; Itzstein, M. Syntheis of Novel Sialylmimetics as Biological Probes. Bioorg. Med. Chem. Lett. 2001, 11, 1587-1590. Lindhorst, T. K. Structure and function of carbohydrates. Naturwiss. Unterr. Chem. 2001, 12, 9-12. Johns, B. A.; Pau, Y. T.; Elbein, A. D. Johnson, C. R. Synthesis and Biological Evaluation of Aza-C-disaccharides: (1→6), (1→4) and (1→1) Linked Sugar Mimics. J. Am. Chem. Soc. 1997, 119, 4856-4865. Musser, J. H.; Anderson, M. B.; Levy, D. E. Glycomimetics as selectin inhibitors. Curr. Pharm. Des. 1995, 1, 221-232.
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6. Vogel, P. Monosacharide and Disaccharide Mimics: New Molecular Tools for Biology and Medicine. Chimia 2001, 55, 359-365 and ref. cited therein. Feizi, T. Oligosaccharides that mediate mammalian cell-cell adhesion. Curr. Opin. Struct. Biol. 1993, 3, 701-710. Bradley, S. J.; Fazli, A.; Kiefel, M. J.; Itzstein, M. Syntheis of Novel Sialylmimetics as Biological Probes. Bioorg. Med. Chem. Lett. 2001, 11, 1587-1590. Lindhorst, T. K. Structure and function of carbohydrates. Naturwiss. Unterr. Chem. 2001, 12, 9-12. Johns, B. A.; Pau, Y. T.; Elbein, A. D. Johnson, C. R. Synthesis and Biological Evaluation of Aza-C-disaccharides: (1→6), (1→4) and (1→1) Linked Sugar Mimics. J. Am. Chem. Soc. 1997, 119, 4856-4865. Musser, J. H.; Anderson, M. B.; Levy, D. E. Glycomimetics as selectin inhibitors. Curr. Pharm. Des. 1995, 1, 221-232.
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15. Bols, M. Apparent Transition State Analogues of Equatorial Glycosides Formation/Cleavage. Acc. Chem. Res. 1998, 31, 1-8. Sears, P.; Wong, C.-H. Carbohydrate Mimietics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition. Angew. Chem., Int. Ed. 1999, 38, 2300-2324. Barchi, J. J. Jr. Emerging Roles of Carbohydrates and Glycomimetics in Anticancer Drug Design. Curr. Pharm. Des. 2000, 6, 485-501. Musser, J. H.; Andersen, M. B.; Fugedi, P. Glycomimetics: an Approach to Discovering Leads for Novel Therapeutics. Pharm. News 1996, 3, 11-17. Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Protective Effects of Oligosaccharides in P-selectin-dependent Lung Injury. Nature 1993, 364, 149-151. Ragupathi, G.; Howard, L.; Cappello, S.; Kogarty, R. R.; Qiu, D.; Longenecker, B. M.; Reddish, M. A.; Lloyd, K. O.; Livingston, P. O. Vaccines Prepared with Sialyl-Tn and Sialyl-Tn Trimers Using the 4-(4-maleimidomethyl)-cyclohexane-l-carboxyl hydrazide Linker Group Result in Optimal Antibody Titers against Ovine Submaxillary Mucin and Sialyl-Tn-positive Tumor Cells. Cancer Immunol. Immunother. 1999, 48, 1-8. MacLean, G. D.; Longenecker, B. M. New Possibilities for Cancer Therapy with Advances in Cancer Immunology. Can. J. Oncology 1994, 4, 249-254. MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gandhi, S.; Smolenski, M.; Samuel, J. Nabholtz, J. M.; Longenecker, B. M. Immunization of Breast Cancer Patients Using a Synthetic Sialyl-Tn Glycoconjugate plus Detox Adjuvant. Cancer Immunol. Immunother. 1993, 36, 215-222. Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Prevention of Lysomal Storage in Tay-Sachs Mice Treated with N-Butyldeoxynojirimycin. Science 1997, 276, 428-431.
16. Bols, M. Apparent Transition State Analogues of Equatorial Glycosides Formation/Cleavage. Acc. Chem. Res. 1998, 31, 1-8. Sears, P.; Wong, C.-H. Carbohydrate Mimietics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition. Angew. Chem., Int. Ed. 1999, 38, 2300-2324. Barchi, J. J. Jr. Emerging Roles of Carbohydrates and Glycomimetics in Anticancer Drug Design. Curr. Pharm. Des. 2000, 6, 485-501. Musser, J. H.; Andersen, M. B.; Fugedi, P. Glycomimetics: an Approach to Discovering Leads for Novel Therapeutics. Pharm. News 1996, 3, 11-17. Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Protective Effects of Oligosaccharides in P-selectin-dependent Lung Injury. Nature 1993, 364, 149-151. Ragupathi, G.; Howard, L.; Cappello, S.; Kogarty, R. R.; Qiu, D.; Longenecker, B. M.; Reddish, M. A.; Lloyd, K. O.; Livingston, P. O. Vaccines Prepared with Sialyl-Tn and Sialyl-Tn Trimers Using the 4-(4-maleimidomethyl)-cyclohexane-l-carboxyl hydrazide Linker Group Result in Optimal Antibody Titers against Ovine Submaxillary Mucin and Sialyl-Tn-positive Tumor Cells. Cancer Immunol. Immunother. 1999, 48, 1-8. MacLean, G. D.; Longenecker, B. M. New Possibilities for Cancer Therapy with Advances in Cancer Immunology. Can. J. Oncology 1994, 4, 249-254. MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gandhi, S.; Smolenski, M.; Samuel, J. Nabholtz, J. M.; Longenecker, B. M. Immunization of Breast Cancer Patients Using a Synthetic Sialyl-Tn Glycoconjugate plus Detox Adjuvant. Cancer Immunol. Immunother. 1993, 36, 215-222. Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Prevention of Lysomal Storage in Tay-Sachs Mice Treated with N-Butyldeoxynojirimycin. Science 1997, 276, 428-431.
17. Bols, M. Apparent Transition State Analogues of Equatorial Glycosides Formation/Cleavage. Acc. Chem. Res. 1998, 31, 1-8. Sears, P.; Wong, C.-H. Carbohydrate Mimietics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition. Angew. Chem., Int. Ed. 1999, 38, 2300-2324. Barchi, J. J. Jr. Emerging Roles of Carbohydrates and Glycomimetics in Anticancer Drug Design. Curr. Pharm. Des. 2000, 6, 485-501. Musser, J. H.; Andersen, M. B.; Fugedi, P. Glycomimetics: an Approach to Discovering Leads for Novel Therapeutics. Pharm. News 1996, 3, 11-17. Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Protective Effects of Oligosaccharides in P-selectin-dependent Lung Injury. Nature 1993, 364, 149-151. Ragupathi, G.; Howard, L.; Cappello, S.; Kogarty, R. R.; Qiu, D.; Longenecker, B. M.; Reddish, M. A.; Lloyd, K. O.; Livingston, P. O. Vaccines Prepared with Sialyl-Tn and Sialyl-Tn Trimers Using the 4-(4-maleimidomethyl)-cyclohexane-l-carboxyl hydrazide Linker Group Result in Optimal Antibody Titers against Ovine Submaxillary Mucin and Sialyl-Tn-positive Tumor Cells. Cancer Immunol. Immunother. 1999, 48, 1-8. MacLean, G. D.; Longenecker, B. M. New Possibilities for Cancer Therapy with Advances in Cancer Immunology. Can. J. Oncology 1994, 4, 249-254. MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gandhi, S.; Smolenski, M.; Samuel, J. Nabholtz, J. M.; Longenecker, B. M. Immunization of Breast Cancer Patients Using a Synthetic Sialyl-Tn Glycoconjugate plus Detox Adjuvant. Cancer Immunol. Immunother. 1993, 36, 215-222. Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Prevention of Lysomal Storage in Tay-Sachs Mice Treated with N-Butyldeoxynojirimycin. Science 1997, 276, 428-431.
18. Bols, M. Apparent Transition State Analogues of Equatorial Glycosides Formation/Cleavage. Acc. Chem. Res. 1998, 31, 1-8. Sears, P.; Wong, C.-H. Carbohydrate Mimietics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition. Angew. Chem., Int. Ed. 1999, 38, 2300-2324. Barchi, J. J. Jr. Emerging Roles of Carbohydrates and Glycomimetics in Anticancer Drug Design. Curr. Pharm. Des. 2000, 6, 485-501. Musser, J. H.; Andersen, M. B.; Fugedi, P. Glycomimetics: an Approach to Discovering Leads for Novel Therapeutics. Pharm. News 1996, 3, 11-17. Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Protective Effects of Oligosaccharides in P-selectin-dependent Lung Injury. Nature 1993, 364, 149-151. Ragupathi, G.; Howard, L.; Cappello, S.; Kogarty, R. R.; Qiu, D.; Longenecker, B. M.; Reddish, M. A.; Lloyd, K. O.; Livingston, P. O. Vaccines Prepared with Sialyl-Tn and Sialyl-Tn Trimers Using the 4-(4-maleimidomethyl)-cyclohexane-l-carboxyl hydrazide Linker Group Result in Optimal Antibody Titers against Ovine Submaxillary Mucin and Sialyl-Tn-positive Tumor Cells. Cancer Immunol. Immunother. 1999, 48, 1-8. MacLean, G. D.; Longenecker, B. M. New Possibilities for Cancer Therapy with Advances in Cancer Immunology. Can. J. Oncology 1994, 4, 249-254. MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gandhi, S.; Smolenski, M.; Samuel, J. Nabholtz, J. M.; Longenecker, B. M. Immunization of Breast Cancer Patients Using a Synthetic Sialyl-Tn Glycoconjugate plus Detox Adjuvant. Cancer Immunol. Immunother. 1993, 36, 215-222. Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Prevention of Lysomal Storage in Tay-Sachs Mice Treated with N-Butyldeoxynojirimycin. Science 1997, 276, 428-431.
19. Bols, M. Apparent Transition State Analogues of Equatorial Glycosides Formation/Cleavage. Acc. Chem. Res. 1998, 31, 1-8. Sears, P.; Wong, C.-H. Carbohydrate Mimietics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition. Angew. Chem., Int. Ed. 1999, 38, 2300-2324. Barchi, J. J. Jr. Emerging Roles of Carbohydrates and Glycomimetics in Anticancer Drug Design. Curr. Pharm. Des. 2000, 6, 485-501. Musser, J. H.; Andersen, M. B.; Fugedi, P. Glycomimetics: an Approach to Discovering Leads for Novel Therapeutics. Pharm. News 1996, 3, 11-17. Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Protective Effects of Oligosaccharides in P-selectin-dependent Lung Injury. Nature 1993, 364, 149-151. Ragupathi, G.; Howard, L.; Cappello, S.; Kogarty, R. R.; Qiu, D.; Longenecker, B. M.; Reddish, M. A.; Lloyd, K. O.; Livingston, P. O. Vaccines Prepared with Sialyl-Tn and Sialyl-Tn Trimers Using the 4-(4-maleimidomethyl)-cyclohexane-l-carboxyl hydrazide Linker Group Result in Optimal Antibody Titers against Ovine Submaxillary Mucin and Sialyl-Tn-positive Tumor Cells. Cancer Immunol. Immunother. 1999, 48, 1-8. MacLean, G. D.; Longenecker, B. M. New Possibilities for Cancer Therapy with Advances in Cancer Immunology. Can. J. Oncology 1994, 4, 249-254. MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gandhi, S.; Smolenski, M.; Samuel, J. Nabholtz, J. M.; Longenecker, B. M. Immunization of Breast Cancer Patients Using a Synthetic Sialyl-Tn Glycoconjugate plus Detox Adjuvant. Cancer Immunol. Immunother. 1993, 36, 215-222. Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Prevention of Lysomal Storage in Tay-Sachs Mice Treated with N-Butyldeoxynojirimycin. Science 1997, 276, 428-431.
20. Bols, M. Apparent Transition State Analogues of Equatorial Glycosides Formation/Cleavage. Acc. Chem. Res. 1998, 31, 1-8. Sears, P.; Wong, C.-H. Carbohydrate Mimietics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition. Angew. Chem., Int. Ed. 1999, 38, 2300-2324. Barchi, J. J. Jr. Emerging Roles of Carbohydrates and Glycomimetics in Anticancer Drug Design. Curr. Pharm. Des. 2000, 6, 485-501. Musser, J. H.; Andersen, M. B.; Fugedi, P. Glycomimetics: an Approach to Discovering Leads for Novel Therapeutics. Pharm. News 1996, 3, 11-17. Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Protective Effects of Oligosaccharides in P-selectin-dependent Lung Injury. Nature 1993, 364, 149-151. Ragupathi, G.; Howard, L.; Cappello, S.; Kogarty, R. R.; Qiu, D.; Longenecker, B. M.; Reddish, M. A.; Lloyd, K. O.; Livingston, P. O. Vaccines Prepared with Sialyl-Tn and Sialyl-Tn Trimers Using the 4-(4-maleimidomethyl)-cyclohexane-l-carboxyl hydrazide Linker Group Result in Optimal Antibody Titers against Ovine Submaxillary Mucin and Sialyl-Tn-positive Tumor Cells. Cancer Immunol. Immunother. 1999, 48, 1-8. MacLean, G. D.; Longenecker, B. M. New Possibilities for Cancer Therapy with Advances in Cancer Immunology. Can. J. Oncology 1994, 4, 249-254. MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gandhi, S.; Smolenski, M.; Samuel, J. Nabholtz, J. M.; Longenecker, B. M. Immunization of Breast Cancer Patients Using a Synthetic Sialyl-Tn Glycoconjugate plus Detox Adjuvant. Cancer Immunol. Immunother. 1993, 36, 215-222. Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Prevention of Lysomal Storage in Tay-Sachs Mice Treated with N-Butyldeoxynojirimycin. Science 1997, 276, 428-431.
21. Bols, M. Apparent Transition State Analogues of Equatorial Glycosides Formation/Cleavage. Acc. Chem. Res. 1998, 31, 1-8. Sears, P.; Wong, C.-H. Carbohydrate Mimietics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition. Angew. Chem., Int. Ed. 1999, 38, 2300-2324. Barchi, J. J. Jr. Emerging Roles of Carbohydrates and Glycomimetics in Anticancer Drug Design. Curr. Pharm. Des. 2000, 6, 485-501. Musser, J. H.; Andersen, M. B.; Fugedi, P. Glycomimetics: an Approach to Discovering Leads for Novel Therapeutics. Pharm. News 1996, 3, 11-17. Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Protective Effects of Oligosaccharides in P-selectin-dependent Lung Injury. Nature 1993, 364, 149-151. Ragupathi, G.; Howard, L.; Cappello, S.; Kogarty, R. R.; Qiu, D.; Longenecker, B. M.; Reddish, M. A.; Lloyd, K. O.; Livingston, P. O. Vaccines Prepared with Sialyl-Tn and Sialyl-Tn Trimers Using the 4-(4-maleimidomethyl)-cyclohexane-l-carboxyl hydrazide Linker Group Result in Optimal Antibody Titers against Ovine Submaxillary Mucin and Sialyl-Tn-positive Tumor Cells. Cancer Immunol. Immunother. 1999, 48, 1-8. MacLean, G. D.; Longenecker, B. M. New Possibilities for Cancer Therapy with Advances in Cancer Immunology. Can. J. Oncology 1994, 4, 249-254. MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gandhi, S.; Smolenski, M.; Samuel, J. Nabholtz, J. M.; Longenecker, B. M. Immunization of Breast Cancer Patients Using a Synthetic Sialyl-Tn Glycoconjugate plus Detox Adjuvant. Cancer Immunol. Immunother. 1993, 36, 215-222. Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Prevention of Lysomal Storage in Tay-Sachs Mice Treated with N-Butyldeoxynojirimycin. Science 1997, 276, 428-431.
22. Bols, M. Apparent Transition State Analogues of Equatorial Glycosides Formation/Cleavage. Acc. Chem. Res. 1998, 31, 1-8. Sears, P.; Wong, C.-H. Carbohydrate Mimietics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition. Angew. Chem., Int. Ed. 1999, 38, 2300-2324. Barchi, J. J. Jr. Emerging Roles of Carbohydrates and Glycomimetics in Anticancer Drug Design. Curr. Pharm. Des. 2000, 6, 485-501. Musser, J. H.; Andersen, M. B.; Fugedi, P. Glycomimetics: an Approach to Discovering Leads for Novel Therapeutics. Pharm. News 1996, 3, 11-17. Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Protective Effects of Oligosaccharides in P-selectin-dependent Lung Injury. Nature 1993, 364, 149-151. Ragupathi, G.; Howard, L.; Cappello, S.; Kogarty, R. R.; Qiu, D.; Longenecker, B. M.; Reddish, M. A.; Lloyd, K. O.; Livingston, P. O. Vaccines Prepared with Sialyl-Tn and Sialyl-Tn Trimers Using the 4-(4-maleimidomethyl)-cyclohexane-l-carboxyl hydrazide Linker Group Result in Optimal Antibody Titers against Ovine Submaxillary Mucin and Sialyl-Tn-positive Tumor Cells. Cancer Immunol. Immunother. 1999, 48, 1-8. MacLean, G. D.; Longenecker, B. M. New Possibilities for Cancer Therapy with Advances in Cancer Immunology. Can. J. Oncology 1994, 4, 249-254. MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gandhi, S.; Smolenski, M.; Samuel, J. Nabholtz, J. M.; Longenecker, B. M. Immunization of Breast Cancer Patients Using a Synthetic Sialyl-Tn Glycoconjugate plus Detox Adjuvant. Cancer Immunol. Immunother. 1993, 36, 215-222. Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Prevention of Lysomal Storage in Tay-Sachs Mice Treated with N-Butyldeoxynojirimycin. Science 1997, 276, 428-431.
23. Bols, M. Apparent Transition State Analogues of Equatorial Glycosides Formation/Cleavage. Acc. Chem. Res. 1998, 31, 1-8. Sears, P.; Wong, C.-H. Carbohydrate Mimietics: A New Strategy for Tackling the Problem of Carbohydrate-Mediated Biological Recognition. Angew. Chem., Int. Ed. 1999, 38, 2300-2324. Barchi, J. J. Jr. Emerging Roles of Carbohydrates and Glycomimetics in Anticancer Drug Design. Curr. Pharm. Des. 2000, 6, 485-501. Musser, J. H.; Andersen, M. B.; Fugedi, P. Glycomimetics: an Approach to Discovering Leads for Novel Therapeutics. Pharm. News 1996, 3, 11-17. Mulligan, M. S.; Paulson, J. C.; DeFrees, S.; Zheng, Z. L.; Lowe, J. B.; Ward, P. A. Protective Effects of Oligosaccharides in P-selectin-dependent Lung Injury. Nature 1993, 364, 149-151. Ragupathi, G.; Howard, L.; Cappello, S.; Kogarty, R. R.; Qiu, D.; Longenecker, B. M.; Reddish, M. A.; Lloyd, K. O.; Livingston, P. O. Vaccines Prepared with Sialyl-Tn and Sialyl-Tn Trimers Using the 4-(4-maleimidomethyl)-cyclohexane-l-carboxyl hydrazide Linker Group Result in Optimal Antibody Titers against Ovine Submaxillary Mucin and Sialyl-Tn-positive Tumor Cells. Cancer Immunol. Immunother. 1999, 48, 1-8. MacLean, G. D.; Longenecker, B. M. New Possibilities for Cancer Therapy with Advances in Cancer Immunology. Can. J. Oncology 1994, 4, 249-254. MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gandhi, S.; Smolenski, M.; Samuel, J. Nabholtz, J. M.; Longenecker, B. M. Immunization of Breast Cancer Patients Using a Synthetic Sialyl-Tn Glycoconjugate plus Detox Adjuvant. Cancer Immunol. Immunother. 1993, 36, 215-222. Platt, F. M.; Neises, G. R.; Reinkensmeier, G.; Townsend, M. J.; Perry, V. H.; Proia, R. L.; Winchester, B.; Dwek, R. A.; Butters, T. D. Prevention of Lysomal Storage in Tay-Sachs Mice Treated with N-Butyldeoxynojirimycin. Science 1997, 276, 428-431.
24. Du, Y.; Lindhardt, F. J.; Vlahov, I. R. Recent Advances in Stereoselective C-Glycoside Synthesis. Tetrahedron 1998, 54, 9913-9959. Levy, D. E.; Tang, C. In The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon-Elsevier Science: Oxford, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Stereoselective Synthesis of C-Disaccharides, Aza-C-Disaccharides and C-Glycosides of Carbapyranoses using "Naked Sugars". In Carbohydrate Mimics; Chapleur, Y., Ed.; Wiley VCH, 1998; 19-48.
25. Du, Y.; Lindhardt, F. J.; Vlahov, I. R. Recent Advances in Stereoselective C-Glycoside Synthesis. Tetrahedron 1998, 54, 9913-9959. Levy, D. E.; Tang, C. In The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon-Elsevier Science: Oxford, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Stereoselective Synthesis of C-Disaccharides, Aza-C-Disaccharides and C-Glycosides of Carbapyranoses using "Naked Sugars". In Carbohydrate Mimics; Chapleur, Y., Ed.; Wiley VCH, 1998; 19-48.
26. Du, Y.; Lindhardt, F. J.; Vlahov, I. R. Recent Advances in Stereoselective C-Glycoside Synthesis. Tetrahedron 1998, 54, 9913-9959. Levy, D. E.; Tang, C. In The Chemistry of C-Glycosides; Tetrahedron Organic Chemistry Series, Baldwin, J. E.; Magnus, P. D., Eds.; Pergamon-Elsevier Science: Oxford, 1995. Vogel, P.; Ferritto, R.; Kraehenbuehl, K.; Baudat, A. Stereoselective Synthesis of C-Disaccharides, Aza-C-Disaccharides and C-Glycosides of Carbapyranoses using "Naked Sugars". In Carbohydrate Mimics; Chapleur, Y., Ed.; Wiley VCH, 1998; 19-48.
27. a) Kraehenbuehl, K.; Picasso, S.; Vogel, P. Synthesis of C-Linked Imino Disaccharides (= Aza-C-disaccharides) with a Pyrrolidine-3,4-diol Moiety Attached at C(3) of Galactose via a Hydroxymethylene Linker and of a 7-(1,2,3-Trihydroxypropyl)-octahydroindolizine-1,2,6,8-tetrol. Helv. Chim. Acta 1998, 81, 1439-1479.
28. b) Pasquarello, C.; Demange, R.; Vogel, P. Synthesis of α-C(1→3)-Mannopyranoside of N-Acetylgalactosamine, a new β-Galactosidase Inhibitor. Bioorg. Med. Chem. Lett. 1999, 9, 793-796.
29. Leeuwenburgh, M. A.; Picasso, S.; Overkleeft, H. S.; Van der Marel, G. A.; Vogel, P.; Van Boom, J. H. A Short and Flexible Route to Aza-β-(1→6)-C-disaccharides: Selective α-Glycosidase Inhibitors. Eur. J. Org. Chem. 1999, 1185-1189.
30. Pasquarello, C.; Picasso, S.; Demange, R.; Malissard, M.; Berger, E. G.; Vogel, P. The C-Disaccharide a-C(1→3)-Mannopyranoside of N-Acetylgalactosamine Is an Inhibitor of Glycohydrolases and of Human α-1,3-Fucosyltransferase VI. Its Epimer α-(1→3)-Mannopyranoside of N-Acetyltalosamine Is Not. J. Org. Chem. 2000, 65, 4251-4260.
31. See, e.g.: Rye, P. D.; Bovin, N. V.; Vlasova, E. V. Walker, R. A. Monoclonal antibody LU-BCRU-G7 against a breast tumour-associated glycoprotein recognizes the disaccharide Ga1β1-3G1cNAc. Glycobiology 1995, 5, 385-389. Kuduk, S. D.; Schwarz, J. B.; Chen, X.-T.; Glunz, P. W.; Sames, D.; Ragupathi, G.; Livingston, P. O.; Danishefski, S. J. Synthetic and Immunological Studies on Clustered Modes of Mucin-related Tn and TF O-Linked Antigens: The Preparation of a Glycopeptide-Based Vaccine for Clinical Trials against Prostate Cancer. J. Am. Chem. Soc. 1998, 120, 12474-12485. Zhu, Y.-H.; Vogel, P. Synthesis of a C-Disaccharide Analog of the Thomsen-Friedenreich (T) Epitope. Synlett 2001, 79-81. Cooper, D. K. C.; Good, A. H.; Koren, E.; Oriol, R.; Macolm, A. J.; Ippolito, R. M.; Neethling, F. A.; Ye, Y.; Romano, E.; Zuhdi, N. Identification of α-Galactosyl and other Carbohydrate Epitopes that are bound by Human anti-pig Antibodies: Relevance to Discordant Xenografting in Man. Transplant. Immunol. 1993, 1, 198-205.
32. See, e.g.: Rye, P. D.; Bovin, N. V.; Vlasova, E. V. Walker, R. A. Monoclonal antibody LU-BCRU-G7 against a breast tumour-associated glycoprotein recognizes the disaccharide Ga1β1-3G1cNAc. Glycobiology 1995, 5, 385-389. Kuduk, S. D.; Schwarz, J. B.; Chen, X.-T.; Glunz, P. W.; Sames, D.; Ragupathi, G.; Livingston, P. O.; Danishefski, S. J. Synthetic and Immunological Studies on Clustered Modes of Mucin-related Tn and TF O-Linked Antigens: The Preparation of a Glycopeptide-Based Vaccine for Clinical Trials against Prostate Cancer. J. Am. Chem. Soc. 1998, 120, 12474-12485. Zhu, Y.-H.; Vogel, P. Synthesis of a C-Disaccharide Analog of the Thomsen-Friedenreich (T) Epitope. Synlett 2001, 79-81. Cooper, D. K. C.; Good, A. H.; Koren, E.; Oriol, R.; Macolm, A. J.; Ippolito, R. M.; Neethling, F. A.; Ye, Y.; Romano, E.; Zuhdi, N. Identification of α-Galactosyl and other Carbohydrate Epitopes that are bound by Human anti-pig Antibodies: Relevance to Discordant Xenografting in Man. Transplant. Immunol. 1993, 1, 198-205.
33. See, e.g.: Rye, P. D.; Bovin, N. V.; Vlasova, E. V. Walker, R. A. Monoclonal antibody LU-BCRU-G7 against a breast tumour-associated glycoprotein recognizes the disaccharide Ga1β1-3G1cNAc. Glycobiology 1995, 5, 385-389. Kuduk, S. D.; Schwarz, J. B.; Chen, X.-T.; Glunz, P. W.; Sames, D.; Ragupathi, G.; Livingston, P. O.; Danishefski, S. J. Synthetic and Immunological Studies on Clustered Modes of Mucin-related Tn and TF O-Linked Antigens: The Preparation of a Glycopeptide-Based Vaccine for Clinical Trials against Prostate Cancer. J. Am. Chem. Soc. 1998, 120, 12474-12485. Zhu, Y.-H.; Vogel, P. Synthesis of a C-Disaccharide Analog of the Thomsen-Friedenreich (T) Epitope. Synlett 2001, 79-81. Cooper, D. K. C.; Good, A. H.; Koren, E.; Oriol, R.; Macolm, A. J.; Ippolito, R. M.; Neethling, F. A.; Ye, Y.; Romano, E.; Zuhdi, N. Identification of α-Galactosyl and other Carbohydrate Epitopes that are bound by Human anti-pig Antibodies: Relevance to Discordant Xenografting in Man. Transplant. Immunol. 1993, 1, 198-205.
34. See, e.g.: Rye, P. D.; Bovin, N. V.; Vlasova, E. V. Walker, R. A. Monoclonal antibody LU-BCRU-G7 against a breast tumour-associated glycoprotein recognizes the disaccharide Ga1β1-3G1cNAc. Glycobiology 1995, 5, 385-389. Kuduk, S. D.; Schwarz, J. B.; Chen, X.-T.; Glunz, P. W.; Sames, D.; Ragupathi, G.; Livingston, P. O.; Danishefski, S. J. Synthetic and Immunological Studies on Clustered Modes of Mucin-related Tn and TF O-Linked Antigens: The Preparation of a Glycopeptide-Based Vaccine for Clinical Trials against Prostate Cancer. J. Am. Chem. Soc. 1998, 120, 12474-12485. Zhu, Y.-H.; Vogel, P. Synthesis of a C-Disaccharide Analog of the Thomsen-Friedenreich (T) Epitope. Synlett 2001, 79-81. Cooper, D. K. C.; Good, A. H.; Koren, E.; Oriol, R.; Macolm, A. J.; Ippolito, R. M.; Neethling, F. A.; Ye, Y.; Romano, E.; Zuhdi, N. Identification of α-Galactosyl and other Carbohydrate Epitopes that are bound by Human anti-pig Antibodies: Relevance to Discordant Xenografting in Man. Transplant. Immunol. 1993, 1, 198-205.
35. Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. Preferred Conformation of C-Glycosides. 14. Synthesis and Conformational Analysis of Carbon Analogs of the Blood Group Determinant H-Type II. J. Org. Chem. 1995, 60, 2160-2169.
36. Rekaï, E. D.; Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Stereoselective Synthesis of α-C-L-Fucopyranosyl Containing C-Disaccharides. Synlett 1998, 831-834.
37. Bimwala, R. M.; Vogel, P. Synthesis of α-(1→2)-, α-(1→3)-, α-(1→4)-, and α-(1→5)-C-Linked Disaccharides through 2,3,4,6-Tetra-O-acetylglucopyranosyl Radical Additions to 3-Methylidene-7-oxabicyclo[2.2.1]heptan-2-one Derivatives. J. Org. Chem. 1992, 57, 2076-2083.
38. Giese, B.; Witzel, T. Synthesis of C-Disaccharides by Radical C-C Bond Formation. Angew. Chem. Int. Ed. Engl. 1986, 25, 450-451.
39. See also: a) Ferritto, R.; Vogel, P. Synthesis of α-D-(1→3) and α-D-(1I-»4)-C-Iinked Galactosides of D-Mannose Derivatives. Conformation of α-C-Galactosides. Tetrahedron: Asymmetry 1994, 5, 2077-2092.
40. b) Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. Reductive Oxa Ring Opening of 7-Oxabicyclo[2.2.1]heptan-2-ones. Synthesis of C-α-Galactosides of Carbapentopyranoses. J. Org. Chem. 1995, 60, 8351-8359.
41. Ferritto, R.; Vogel, P. Stereoselective Synthesis of α-C-Galactopyranosides of Conduritols and Aminoconduritols. Synlett 1996, 281-282.
42. Vieira, E.; Vogel, P. Copper(I)-and Copper(II)-catalyzed Diels-Alder Additions of α-Substituted Acrylonitrile to Furan. The Synthesis of 7-Oxabicyclo[2.2.1]hept-5-en-2-one. Helv. Chim. Acta 1982, 65, 1700-1706.
43. Abbott, S. D.; Gagnon, L.; Lagraoui, M.; Kadhim, S.; Attardo, G.; Zaccharie, B.; Penney, C. L. Synthesis and Activity of Dipeptides, Linked to Targeting Ligands, as Specific NK Cell Enhancers. J. Med. Chem. 1998, 41, 1909-1926.
44. Forster, A.; Kovac, T.; Mosimann, H.; Renaud, P.; Vogel, P. Resolution of 7-oxabicyclo[2.2.1]hept-5-en-2-one via cyclic aminals. Tetrahedron: Asymmetry 1999, 10, 567-571.
45. Schmidt, R. R. New Methods for the Synthesis of Glycosides and Oligosaccharides-Are There Alternatives to the Koenigs-Knorr Method? Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235. Schmidt, R. R.; Michel, J. Facile Synthesis of Glycosides and Disaccharides. Angew. Chem. Int. Ed. Engl. 1980, 19, 731-732.
46. Schmidt, R. R. New Methods for the Synthesis of Glycosides and Oligosaccharides-Are There Alternatives to the Koenigs-Knorr Method? Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235. Schmidt, R. R.; Michel, J. Facile Synthesis of Glycosides and Disaccharides. Angew. Chem. Int. Ed. Engl. 1980, 19, 731-732.