Design and synthesis of unnatural heparosan and chondroitin building blocks

Journal of Organic Chemistry

Volumn 76, Issue 9, 2011, Pages 3181-3193

  Bera, Smritilekha ^a   Linhardt, Robert J ^a  

^a Rensselaer Polytechnic Institute   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE-ALKYNE CYCLOADDITION; BUILDING BLOCKES; CHONDROITIN; COPPER CATALYZED; GLUCURONIC ACIDS; N-ACETYL GALACTOSAMINE; STEREOSELECTIVE MANNER; TETRASACCHARIDES;

ACETYLENE; GLUCOSE;

SYNTHESIS (CHEMICAL);

ALKYNE; AZIDE; CHONDROITIN; COPPER; DISACCHARIDE; GLUCURONIC ACID; GLYCOSAMINOGLYCAN POLYSULFATE; N ACETYLGALACTOSAMINE; N ACETYLGLUCOSAMINE; OLIGOSACCHARIDE; TETRASACCHARIDE; TRIAZOLE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; STEREOCHEMISTRY; SYNTHESIS;

ACETYLGLUCOSAMINE; AZIDES; CHONDROITIN; DISACCHARIDES; DRUG DESIGN; HEPARITIN SULFATE; STEREOISOMERISM; SULFATES;

EID: 79955553857     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200076z     Document Type: Article

References (52)

1. McLean, J. Am. J. Physiol. 1916, 41, 250-257
2. Capila, I.; Linhardt, R. J. Angew. Chem., Int. Ed. 2002, 41, 391-412
3. Rabenstein, D. L. Nat. Prod. Rep. 2002, 19, 312-331
4. Damus, P. S.; Hicks, M.; Rosenberg, R. D. Nature 1973, 246, 355-357
5. Rosenberg, R. D.; Damus, P. S. J. Biol. Chem. 1973, 248, 6490-6505
6. Sinaÿ, P.; Jacquinet, J. C.; Petitou, M.; Duchaussoy, P.; Lederman, I.; Choay, J.; Torri, G. Carbohydr. Res. 1984, 132, C5-C9
7. Petitou, M.; Herault, L. P.; Bernat, A.; Driguez, P. A.; Duchaussoy, P.; Lormeau, J. C.; Herbert, J. M. Nature 1999, 398, 417-422
8. Hardingham, T.; Semin, M. B. Arthritis Rheu. 1990, 20, 12-33
9. Fawthrop, F.; Yaqub, R.; Belcher, C.; Bayliss, M.; Ledingham, J.; Doherty, M. Ann. Rheum. Dis. 1997, 56, 119-122
10. Conte, A.; Volpi, N.; Palmieri, L.; Bahous, I.; Ronca, G. Arzneim. Forsch. 1995, 45, 918-925
11. Gressner, A. M.; Koster-Eiserfunke, W.; Van de Leur, E.; Greiling, H. J. Clin. Chem. Clin. Biochem. 1980, 18, 279-285
12. Reference 2a.
13. Das, S. K.; Mallet, J. M.; Esnault, J.; Driguez, P. A.; Duchaussoy, P.; Sizun, P.; Herault, J. P.; Herbert, J. M.; Petitou, M.; Sinaÿ, P. Angew. Chem., Int. Ed. 2001, 40, 1670-1673
14. Raman, R.; Venkataraman, G.; Ernst, S.; Sasisekharan, V.; Sasisekharan, R. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 2357-2362
15. Faham, S.; Linhardt, R. J.; Rees, D. C. Curr. Opin. Struct. Biol. 1998, 8, 578-586
16. Vann, W. F.; Schmidt, M. A.; Jann, B.; Jann, K. Eur. J. Biochem. 1981, 116, 359-364
17. Yamagata, T.; Saito, H.; Habuchi, O; Suzuki, S. J. Biol. Chem. 1968, 243, 1523-1 535
18. Meyer, K.; Palmer, J. W. J. Biol. Chem. 1934, 107, 629-634
19. Knudson, C. B.; Knudson, W. FASEB J. 1993, 7, 1233-1242
20. Fraser, J. R.; Laurent, T. C.; Laurent, U. B. J. Intern. Med. 1997, 242, 27-33
21. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol. 1, pp 1-176.
22. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
23. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chemie. Int. Ed. 2002, 41, 2596-2599
24. Calvo-Flores, F. G.; Isac-García, J.; Hernández-Mateo, F.; Pérez-Balderas, F.; Calvo-Asín, J. A.; Sanchéz-Vaquero, E.; Santoyo-González, F. Org. Lett. 2000, 2, 2499-2502
25. Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Eycken, E. Org. Lett. 2004, 6, 4223-4225
26. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193
27. Sinaÿ, P. Biochimie 1988, 70, 1455-1458
28. Reference 11b.
29. Karst, N. A.; Linhardt, R. J. Curr. Med. Chem. 2003, 10, 1993-2031
30. Lopin, C.; Jacquinet, J. C. Angew. Chem., Int. Ed. 2006, 10, 2574-2578
31. Weiwer, M.; Linhardt, R. J. In Comprehensive Glycosciences, Boons, G. J.; Lee, Y. C.; Suzuki, A.; Taniguchi, N.; Voragen, A. G. J.; Kamerling, J. P., Eds.; Elsevier BV: Amsterdam, 2007; pp 713-745.
32. Polat, T.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 12795-12800
33. Rawat, M.; Gama, C. I.; Matson, J. B.; Hsieh-Wilson, L. C. J. Am. Chem. Soc. 2008, 130, 2959-2961
34. Arungundram, S.; Al-Mafraji, K.; Asong, J.; Leach, F. E., III; Amster, I. J.; Venot, A.; Turnbull, J. E.; G.-J. J. Am. Chem. Soc. 2009, 131, 17394-17405
35. Leendert, J.; van den Bos; Jeroen, D. C.; Codée, J. C; van der Toorn; Boltje, T. J.; van Boom, J. H.; Overkleeft, H. S.; van der Marel, G. A. Org. Lett. 2004, 6, 2165-2168
36. Anjos, J. V. Dos; Sinou, D.; Melo, S. J. De; Srivastava, R. M. Carbohydr. Res. 2007, 342, 2440-2449
37. Veeneman, G. H.; van Leeuwen, S. H.; Van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331-1334
38. Huang, L.; Huang, X. Chem. - Eur. J. 2007, 13, 529-540
39. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212-235
40. Schmidt, R. R. Pure Appl. Chem. 1989, 61, 1257-1270
41. Schmidt, R. R. In Modern Methods in Carbohydrate Synthesis; Khan, S. H.; O'Neil, R. A., Eds.; Harwood: The Netherlands, 1996; pp 20-54.
42. Klotz, W.; Schmidt, R. R. Liebigs Ann. Chem. 1993, 683-690
43. Vauzeilles, B.; Dausse, B.; Palmier, S.; Beau, J.-M. Tetrahedron Lett. 2001, 42, 7567-7570
44. Sharma, M.; Bernacki, R. J.; Hillman, M. J.; Korytnyk, W. Carbohydr. Res. 1990, 198, 205-221
45. Christensen, H.; Christiansen, M. S.; Petersen, J.; Jensen., H. H. Org. Biomol. Chem. 2008, 6, 3276-3283
46. Sheryl, D. D.; Eric, J. T. Tetrahedron: Asymmetry 2000, 11, 385-387
47. Fernandez-Bolanos, J. G.; Garcia, S.; Fernandez-Bolanos, J.; Dianez, M. J.; Estrada, M. D.; Lopez-Castro, A.; Perez-Garrido, S. Tetrahedron: Asymmetry 2003, 14, 3761-3768
48. Bera, S.; Zhanel, G. G.; Schweizer, F. Bioorg. Med. Chem. Lett. 2010, 20, 3031-3035
49. Ikeda, K.; Sato, K.; Kitani, S.; Suzuki, T.; Maki, N.; Suzukib, Y.; Sato, M. Bioorg. Med. Chem. 2006, 14, 7893-7897
50. Kim, Jin-H.; Huang, F.; Ly, M.; Robert, L. J. J. Org. Chem. 2008, 73, 9497-9500
51. Hudlicky, T.; Moser, M.; Banfield, S. C.; Rinner, U.; Jean-Charles, C.; George, R. P. Can. J. Chem. 2006, 84, 1313-1337
52. Adrio, J.; Carretero, J. C. J. Am. Chem. Soc. 2007, 129, 778-779