Combinatorial Chemistry toward Understanding the Function(s) of Carbohydrates and Carbohydrate Conjugates
2001; Wiley; Volume: 7; Issue: 3 Linguagem: Francês
10.1002/1521-3765(20010202)7
ISSN1521-3765
Autores Tópico(s)Chemical Synthesis and Analysis
ResumoChemistry – A European JournalVolume 7, Issue 3 p. 555-563 Concept Combinatorial Chemistry toward Understanding the Function(s) of Carbohydrates and Carbohydrate Conjugates Angela Barkley Dr., Angela Barkley Dr. Chemical Biology Program Steacie Institute for Molecular Sciences National Research Council of Canada 100 Sussex Drive, Ottawa, ON, K1A 0R6 (Canada) Fax (+1) 613-952-0068Search for more papers by this authorPrabhat Arya Prof. Dr., Prabhat Arya Prof. Dr. [email protected] Chemical Biology Program Steacie Institute for Molecular Sciences National Research Council of Canada 100 Sussex Drive, Ottawa, ON, K1A 0R6 (Canada) Fax (+1) 613-952-0068Search for more papers by this author Angela Barkley Dr., Angela Barkley Dr. Chemical Biology Program Steacie Institute for Molecular Sciences National Research Council of Canada 100 Sussex Drive, Ottawa, ON, K1A 0R6 (Canada) Fax (+1) 613-952-0068Search for more papers by this authorPrabhat Arya Prof. Dr., Prabhat Arya Prof. Dr. [email protected] Chemical Biology Program Steacie Institute for Molecular Sciences National Research Council of Canada 100 Sussex Drive, Ottawa, ON, K1A 0R6 (Canada) Fax (+1) 613-952-0068Search for more papers by this author First published: 26 January 2001 https://doi.org/10.1002/1521-3765(20010202)7:3 3.0.CO;2-ICitations: 35Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract The complexity and synthetic challenges of carbohydrate conjugates have resulted in a number of conceptual approaches to rapidly access sufficient quantities of these biomolecules (see figure for a carbohydrate conjugate building block with its potential diversity sites). This article summarizes these combinatorial approaches and also highlights fully automated library synthesis of carbohydrate conjugates, with the goals of understanding their biological roles. Abstract Combinatorial chemistry has contributed significantly to understanding the structure–function relationships of biologically important molecules such as proteins and nucleic acids. However, carbohydrates and carbohydrate conjugates, which have been identified as key modulators of several biological functions have not enjoyed the same measure of success. The complexity and synthetic challenges of carbohydrate conjugates have resulted in a number of conceptual approaches to rapidly access sufficient quantities of these biomolecules. This article summarizes these combinatorial approaches and also highlights fully automated library synthesis of artificial glycopeptides with the goals of understanding their biological roles. References 1 R. A. Dwek, Chem. Rev. 1996, 96, 683; A. Varki, Glycobiology 1993, 3, 97. 2 J. Ø. Duus, P. M. St. Hilaire, M. Meldal, K. Bock, Pure Appl. Chem. 1999, 71, 755; P. Mischnick, Angew. Chem. 2000, 112, 1274; Angew. Chem. Int. Ed. 2000, 39, 1222. 3 See for example: Preparative Carbohydrate Chemistry ( ), Marcel Dekker, 1997; G. Benjamin, J. Davis, J. Chem. Soc. Perkin Trans. 1 2000, 2137; K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503. 4 S. J. Danishefsky, J. Y. Roberge, Pure Appl. Chem. 1995, 67, 1647; C. Gege, J. Vogel, G. Bendas, U. Rothe, R. R. Schmidt, Chem. Eur. J. 2000, 6, 111; D. K. Baeschlin, A. R. Chaperon, L. G. Green, M. H. Hahn, S. J. Ince, S. V. Ley, Chem. Eur. J. 2000, 6, 172; J. G. Allen, B. Fraser-Reid, J. Am. Chem. Soc. 1999, 121, 468; G. A. Winterfield, Y. Ito, T. Ogawa, R. R. Schmidt, Eur. J. Org. Chem. 1999, 1167; J. Habermann, H. Kunz, Tetrahedron Lett. 1998, 39, 265; P. H. Seeberger, S. J. Danishefsky, Acc. Chem. Res. 1998, 31, 685; C. Unverzagt, Carbohydr. Res. 1998, 305, 423; E. Meinjohanns, M. Meldal, H. Paulsen, R. A. Dwek, K. Bock, J. Chem. Soc. Perkin Trans. 1 1998, 549; D. Sames, X.-T. Chen, S. J. Danishefsky, Nature 1997, 389, 587; O. Seitz, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 8766; N. Mathieux, H. Paulsen, M. Meldal, K. Bock, J. Chem. Soc. Perkin Trans. 1 1997, 2359; S. J. Danishefsky, M. T. Bilodeau, Angew. Chem. 1996, 108, 1482; Angew. Chem. Int. Ed. Engl. 1996, 35, 1380; Z.-G. Wang, X.-F. Zhang, Y. Ito, Y. Nakahara, T. Ogawa, Carbohydr. Res. 1996, 295, 25; 5 L. A. Marcaurelle, C. R. Bertozzi, Chem. Eur. J. 1999, 5, 1384; E. E. Simanek, G. J. McGarvey, J. A. Jablonowski, C.-H. Wong, Chem. Rev. 1998, 98, 833; P. Sears, C.-H. Wong, Angew. Chem. 1999, 111, 2446; Angew. Chem. Int. Ed. 1999, 38, 2300; P. M. St. Hilaire, M. Meldal, Angew. Chem. 2000, 112, 1210; Angew. Chem. Int. Ed. 2000, 39, 1162. 6 L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 95, 555; E. M. Gordon, M. A. Gallop, D. V. Patel, Acc. Chem. Res. 1996, 29, 144; K. S. Lam, M. Lebel, V. Krchnak, Chem. Rev. 1997, 97, 411; R. E. Dolle, K. H. Nelson, Jr., J. Comb. Chem. 1999, 1, 235; F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288; F. Guillier, D. Orain, M. Bradley, Chem. Rev. 2000, 100, 2091. 7 R. B. Merrifield J. Am. Chem. Soc. 1963, 85, 2149; A. Furka, F. Sebestyen, M. Asgedom, G. Dibo, Int. J. Peptide Protein Res. 1991, 37, 487; R. A. Houghten, C. Pinilla, S. E. Blondelle, J. R. Appel, C. T. Dooley, J. H. Cuervo, Nature 1991, 354, 84. 8 Combinatorial Chemistry and Molecular Diversity in Drug Discovery ( ), Wiley, 1998; Molecular Diversity and Combinatorial Chemistry—Libraries and Drug Discovery ( ), ACS Series, 1996; D. Obrecht, J. M. Villalgordo in Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries, Pergamon, 1998; Solid Phase Organic Synthesis ( ), Wiley, New York, 2000. 9 See special Issue 2 on combinatorial chemistry: Chem. Rev. 1997, 97. 10 M. J. Sofia, Mol. Diversity 1998, 3, 75; Z.-G. Wang, O. Hindsgaul, Glycoimmunology 1998, 2, 219; F. Schweizer, O. Hindsgaul, Curr. Opin. Chem. Biol. 1999, 3, 291; P. Arya, R. N. Ben, Angew. Chem. 1997, 109, 1335; Angew. Chem. Int. Ed. Engl. 1997, 36, 1280. 11 O. Kanie, F. Berresi, Y. Ding, J. Labbe, A. Otter, L. S. Forsberg, B. Ernst, O. Hindsgaul, Angew. Chem. 1995, 107, 2912; Angew. Chem. Int. Ed. Engl. 1995, 34, 2720. 12 Y. Ding, J. Labbe, O. Kanie, O. Hindsgaul, Bioorg. Med. Chem. 1996, 4, 683. 13 G.-J. Boons, B. Heskamp, F. Hout, Angew. Chem. 1996, 108, 3053; Angew. Chem. Int. Ed. Engl. 1996, 35, 2845. 14 G.-J. Boons, S. Isles, J. Org. Chem. 1996, 61, 4262. 15 M. Johnson, C. Arles, G.-J. Boons, Tetrahedron Lett. 1998, 39, 9801. 16 M. Izumi, Y. Ichikawa, Tetrahedron Lett. 1998, 39, 2079. 17 C.-H. Wong, X.-S. Ye, Z. Zhang, J. Am. Chem. Soc. 1998, 120, 7137. 18 A. Lubineau, D. Bonnaffe, Eur. J. Org. Chem. 1999, 2523. 19 Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Bassov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734. 20 X.-S. Ye, C.-H. Wong, J. Org. Chem. 2000, 65, 2410. 21 H. Yamada, T. Kato, T. Takahashi, Tetrahedron Lett. 1999, 40, 4581; T. Takahashi, M. Adachi, A. Matsuda, T. Doi, Tetrahedron Lett. 2000, 41, 2599. 22 H. M. I. Osborn, T. H. Khan, Tetrahedron 1999, 55, 1807. 23 R. Liang, L. Yan, J. Loebach, M. Ge, Y. Uozumi, K. Sekanina, N. Horan, J. Glidersleeve, C. Thompson, A. Smith, K. Biswas, W. C. Still, D. Kahne, Science 1996, 274, 1520; N. Horan, L. Yan, H. Isobe, G. M. Whitesides, D. Kahne, Proc. Natl. Acad. Sci. USA 1999, 96, 11 782. 24 T. Zhu, G.-J. Boons, Angew. Chem. 1998, 110, 2000; Angew. Chem. Int. Ed. 1998, 37, 1898. 25 S. P. Douglas, D. M. Whitfield, J. J. Krepinsky, J. Am. Chem. Soc. 1991, 113, 5095; Y. Ito, O. Kanie, T. Ogawa, Angew. Chem. 1996, 108, 2691; Angew. Chem. Int. Ed. Engl. 1996, 35, 2510; C. M. Dreef-Tromp, H. A. M. Willems, P. Westerduin, P. van Veelen, C. A. A. van Boeckel, Bioorg. Med. Chem. Lett. 1997, 7, 1175. 26 M. Schuster, P. Wang, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 1994, 116, 1135. 27 R. R. Schmidt, Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212; J. Rademann, R. Schmidt, Tetrahedron Lett. 1996, 37, 3989. 28 J. Rademann, R. R. Schmidt, J. Org. Chem. 1997, 62, 3650. 29 L. Knerr, R. R. Schmidt, Synlett 1999, 1802. 30 R. Rodebaugh, S. Joshi, B. Fraser-Reid, H. M. Geysen, J. Org. Chem. 1997, 62, 5660; G. Anilkumar, L. G. Nair, B. Fraser-Reid, Org. Lett. 2000, 2, 2587. 31 R. Andrade, O. J. Plante, L. G. Melean, P. H. Seeberger, Org. Lett. 1999, 1, 1811. 32 C. Zheng, P. H. Seeberger, S. J. Danishefsky J. Org. Chem. 1998, 63, 1126. 33 G. Hummel, O. Hindsgaul, Angew. Chem. 1999, 111, 1900; Angew. Chem. Int. Ed. 1999, 38, 1782. 34 K. C. Nicolaou, N. Watanabe, J. Li., J. Pastor, N. Winssinger, Angew. Chem. 1998, 110, 1636; Angew. Chem. Int. Ed. 1998, 37, 1559. 35 M. J. Sofia, Med. Chem. Res. 1998, 8, 362. 36 R. Hirschmann, W. Yao, M. A. Cascieri, C. D. Strader, L. Maechler, M. A. Cichy-Knight, J. Hynes, Jr., R. D. van Rijn, P. A. Sprengeler, A. B. Smith III, J. Med. Chem. 1996, 39, 2441. 37 M. J. Sofia, R. Hunter, T. Y. Chan, A. Vaughan, R. Dulina, H. Wang, D. Gange, J. Org. Chem. 1998, 63, 2802. 38 K. C. Nicolaou, X. Y. Xiao, Z. Parandoosh, A. Senyei, M. P. Nova, Angew. Chem. 1995, 107, 2476; Angew. Chem. Int. Ed. Engl. 1995, 34, 2289. 39 T. Wunberg, C. Kallus, T. Opatz, S. Henke, W. Schmidt, H. Kunz, Angew. Chem. 1998, 110, 2620; Angew. Chem. Int. Ed. 1998, 37, 2503. 40 C. Kallus, T. Opatz, T. Wunberg, W. Schmidt, S. Henke, H. Kunz, Tetrahedron Lett. 1999, 40, 7783. 41 D. J. Silva, H. Wang, N. M. Allanson, R. K. Jain, M. J. Sofia, J. Org. Chem. 1999, 64, 5926. 42 C.-H. Wong, M. Hendrix, D. D. Manning, C. Rosenbohm, W. A. Greenberg, J. Am. Chem. Soc. 1998, 120, 8319. 43 I. Ugi, Angew. Chem. 1982, 94, 826; Angew. Chem. Int. Ed. Engl. 1982, 21, 810. 44 D. P. Sutherlin, T. M. Stark, R. Hughes, R. W. Armstrong, J. Org. Chem. 1996, 61, 8350. 45 W. K. C. Park, M. Auer, H. Jaksche, C.-H. Wong, J. Am. Chem. Soc. 1996, 118, 10 150. 46 O. Lockhoff, Angew. Chem. 1998, 110, 3634; Angew. Chem. Int. Ed. 1998, 37, 3436. 47 U. J. Nilsson, E. J.-L. Fournier, O. Hindsgaul, Bioorg. Med. Chem. 1998, 6, 1563. 48 M. Meldal, P. M. St. Hilaire, Curr. Opin. Chem. Biol. 1997, 1, 552. 49 P. M. St. Hilaire, T. L. Lowary, M. Meldal, K. Bock, J. Am. Chem. Soc. 1998, 120, 13 312. 50 T. F. J. Lampe, G. Weitz-Schmidt, C.-H. Wong, Angew. Chem. 1998, 110, 1761; Angew. Chem. Int. Ed. 1998, 37, 1707. 51 P. Arya, S. Dion, G. K. H. Shimizu, Bioorg. Med. Chem. Lett. 1997, 7, 1537. 52 P. Arya, K. M. K. Kutterer, H. Qin, J. Roby, M. L. Barnes, J. M. Kim, R. Roy, Bioorg. Med. Chem. Lett. 1998, 8, 1127; P. Arya, K. M. K. Kutterer, H. Qin, J. Roby, M. L. Barnes, S. Lin, C. A. Lingwood, M. G. Peter, Bioorg. Med. Chem. 1999, 7, 2823; P. Arya, R. N. Ben, K. M. K. Kutterer, Organic Synthesis Highlights, Vol. IV, Wiley-VCH, Weinheim, 2000, p. 337. 53 K. M. K. Kutterer, M. L. Barnes, P. Arya, J. Comb. Chem. 1999, 1, 28. 54 P. Arya, K. M. K. Kutterer, A. Barkley, J. Comb. Chem. 2000, 2, 120. 55 A. Barkley, P. Arya, unpublished results. 56 L. Ellgarrd, M. Molinari, A. Helenius, Science 1999, 286, 1882. 57 A. Zapun, C. A. Jakob, D. Y. Thomas, J. J. M. Bergeron, Structure 1999, R173. 58 M. McNeil in Genetics of Bacterial Polysaccharides ( ), CRC, 1999, pp. 207–223. 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