Scope of multivalent ligand function: Lactose-bearing neoglycopolymers by ring-opening metathesis polymerization

Synthesis

Volumn , Issue SPEC. ISS., 1999, Pages 1515-1519

  Pohl, Nicola L ^a   Kiessling, Laura L ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Carbohydrates; Lactose; Lectins; Polyvalency; Ring opening metathesis polymerization

Indexed keywords

GALECTIN; HEMAGGLUTININ; LACTOSE; LACTOSE NEOGLYCOPOLYMER; LIGAND; NORBORNENE DERIVATIVE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL INFECTION; BINDING AFFINITY; COMPLEX FORMATION; INFLAMMATION; LIGAND BINDING; POLYMERIZATION; PROTEIN BINDING; VIRUS INFECTION;

EID: 0032769701     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3659     Document Type: Article

References (32)

1. Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71. Kiessling, L. L.; Strong, L. E. "BioActive Polymers" in Topics in Organometallic Chemistry 1: Alkene Metathesis in Organic Synthesis, 1998, 199. Kiessling, L. L. "The Molecular Recognition of Saccharides and Glycoprotein-Inspired Materials" in Recent Trends in Molecular Recognition, Proceedings of the Ernst Schering Research Foundation Workshop 26, 1998, 183.
2. Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71. Kiessling, L. L.; Strong, L. E. "BioActive Polymers" in Topics in Organometallic Chemistry 1: Alkene Metathesis in Organic Synthesis, 1998, 199. Kiessling, L. L. "The Molecular Recognition of Saccharides and Glycoprotein-Inspired Materials" in Recent Trends in Molecular Recognition, Proceedings of the Ernst Schering Research Foundation Workshop 26, 1998, 183.
3. Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71. Kiessling, L. L.; Strong, L. E. "BioActive Polymers" in Topics in Organometallic Chemistry 1: Alkene Metathesis in Organic Synthesis, 1998, 199. Kiessling, L. L. "The Molecular Recognition of Saccharides and Glycoprotein-Inspired Materials" in Recent Trends in Molecular Recognition, Proceedings of the Ernst Schering Research Foundation Workshop 26, 1998, 183.
4. Roy, R. Curr. Opin. Struct. Biol. 1996, 6, 692.
5. Mammen, M.; Choi, S.-K.; Whitesides, G.M. Angew. Chem. Int. Ed. Engl. 1998, 37, 2754.
6. For examples see: Manning, D.D.; Bertozzi, C.R.; Pohl, N.L.; Rosen, S.D.; Kiessling, L.L. J. Org. Chem. 1995, 60, 6254. Bertozzi, C.R.; Fukuda, S.; Rosen, S.D. Biochemistry 1995, 34, 14271. Bertozzi, C.R. Chem. Biol. 1995, 2, 703. Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B.K. Proc. Natl. Acad. Sci. USA 1991, 88, 10372.
7. For examples see: Manning, D.D.; Bertozzi, C.R.; Pohl, N.L.; Rosen, S.D.; Kiessling, L.L. J. Org. Chem. 1995, 60, 6254. Bertozzi, C.R.; Fukuda, S.; Rosen, S.D. Biochemistry 1995, 34, 14271. Bertozzi, C.R. Chem. Biol. 1995, 2, 703. Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B.K. Proc. Natl. Acad. Sci. USA 1991, 88, 10372.
8. For examples see: Manning, D.D.; Bertozzi, C.R.; Pohl, N.L.; Rosen, S.D.; Kiessling, L.L. J. Org. Chem. 1995, 60, 6254. Bertozzi, C.R.; Fukuda, S.; Rosen, S.D. Biochemistry 1995, 34, 14271. Bertozzi, C.R. Chem. Biol. 1995, 2, 703. Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B.K. Proc. Natl. Acad. Sci. USA 1991, 88, 10372.
9. For examples see: Manning, D.D.; Bertozzi, C.R.; Pohl, N.L.; Rosen, S.D.; Kiessling, L.L. J. Org. Chem. 1995, 60, 6254. Bertozzi, C.R.; Fukuda, S.; Rosen, S.D. Biochemistry 1995, 34, 14271. Bertozzi, C.R. Chem. Biol. 1995, 2, 703. Tyrrell, D.; James, P.; Rao, N.; Foxall, C.; Abbas, S.; Dasgupta, F.; Nashed, M.; Hasegawa, A.; Kiso, M.; Asa, D.; Kidd, J.; Brandley, B.K. Proc. Natl. Acad. Sci. USA 1991, 88, 10372.
10. Barondes, S.H.; Castronovo, V.; Cooper, D.N.W.; Cummings, R.D.; Drickamer, K.; Feizi, T.; Gitt, M.A.; Hirabayashi, J.; Hughes, C.; Kasai, K.-i.; Leffler, H.; Liu, F.-T.; Lotan, R.; Mercurio, A.M.; Monsigny, M.; Pillai, S.; Poirer, F.; Raz, A.; Rigby, P.W.J.; Rini, J.M.; Wang, J.L. Cell 1994, 76, 597. Barondes, S.H.; Cooper, D.N.W.; Gitt, M.A.; Leffler, H. J. Biol. Chem. 1994, 269, 20807.
11. Barondes, S.H.; Castronovo, V.; Cooper, D.N.W.; Cummings, R.D.; Drickamer, K.; Feizi, T.; Gitt, M.A.; Hirabayashi, J.; Hughes, C.; Kasai, K.-i.; Leffler, H.; Liu, F.-T.; Lotan, R.; Mercurio, A.M.; Monsigny, M.; Pillai, S.; Poirer, F.; Raz, A.; Rigby, P.W.J.; Rini, J.M.; Wang, J.L. Cell 1994, 76, 597. Barondes, S.H.; Cooper, D.N.W.; Gitt, M.A.; Leffler, H. J. Biol. Chem. 1994, 269, 20807.
12. For a review see: Toone, E. Curr. Opin. Struct. Biol. 1994, 4, 719.
13. Manning, D. D.; Strong, L. E.; Hu, X.; Beck, P.J.; Kiessling, L. L. Tetrahedron 1997, 53, 11937.
14. Sanders, W.J.; Gordon, E.J.; Dwir, O.; Beck, P.J.; Alon, R.; Kiessling, L.L. J. Biol. Chem. 1999, 274, 5271.
15. Gordon, E.J.; Sanders, W.S.; Kiessling, L.L. Nature 1998, 392, 30.
16. Mann, D.A.; Kanai, M.; Maly, D.J.; Kiessling, L.L. J. Am. Chem. Soc. 1998, 120, 10575.
17. Kasai, K.; Hirabayashi, J. J. Biochem. 1996, 119, 1.
18. Youssef, R.H.; Silwanis, B.A.; El-Sokkary, R.I.; Nematalla, A.S.; Nashed, M.A. Carbohydr. Res. 1993, 240, 287.
19. Crockett, G.C., Swanson, B.J., Anderson, D.R., Koch, T.H. Synth. Commun. 1981, 11, 441.
20. Lynn, D.M.; Kanaoka, S.; Grubbs, R.H. J. Am. Chem. Soc. 1996, 118, 784. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
21. Lynn, D.M.; Kanaoka, S.; Grubbs, R.H. J. Am. Chem. Soc. 1996, 118, 784. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100.
22. Mortell, K.H.; Weatherman, R.V.; Kiessling, L.L. J. Am. Chem. Soc. 1996, 118, 2297. Mortell, K.H.; Gingras, M.; Kiessling, L.L. J. Am. Chem. Soc. 1994, 116, 12053.
23. Mortell, K.H.; Weatherman, R.V.; Kiessling, L.L. J. Am. Chem. Soc. 1996, 118, 2297. Mortell, K.H.; Gingras, M.; Kiessling, L.L. J. Am. Chem. Soc. 1994, 116, 12053.
24. Massa, S.M.; Cooper, D.N.W.; Leffler, H.; Barondes, S.H. Biochemistry 1993, 32, 260. Hsu, D.K., Zuberi, R.I., Liu, F.-T. J. Biol. Chem. 1992, 267, 14167.
25. Massa, S.M.; Cooper, D.N.W.; Leffler, H.; Barondes, S.H. Biochemistry 1993, 32, 260. Hsu, D.K., Zuberi, R.I., Liu, F.-T. J. Biol. Chem. 1992, 267, 14167.
26. Matsuoka, K.; Nishimura, S.-I. Macromolecules 1995, 28, 2961.
27. The Gal-3 binding assay was performed by Paul Hill in the laboratories of Dr. Fu-Tong Liu at the La Jolla Institute for Allergy and Immunology in California. For details see: Pohl, N.L. University of Wisconsin-Madison Ph.D. Thesis, 1997.
28. Kanai, M.; Mortell, K.H.; Kiessling, L.L. J. Am. Chem. Soc. 1997, 199, 9931.
29. Shaanan, B.; Lis, H.; Sharon, N. Science 1991, 254, 862.
30. Derewenda, Z.; Yariv, J.; Helliwell, J.R.; Kalb, A.J.; Dodson, E.J.; Papiz, M.Z.; Wan, T.; Campbell, J. EMBO. 1989, 8, 2189.
31. Frigeri, L.G.; Robertson, M.W.; Liu, F.-T. J. Biol. Chem. 1990, 265, 20763.
32. Yang, R.-Y.; Hill, P.N., Hsu, D.K.; Liu, F.-T. Biochemistry 1998, 37, 4086.