Synthesis of mucin glycans from the protozoon parasite Trypanosoma cruzi

Synlett

Volumn , Issue 14, 2008, Pages 2175-2177

  Van Well, Renate M ^a   Collet, Beatrice Y M ^a   Field, Robert A ^a,b  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

^b JOHN INNES CENTRE   (United Kingdom)

Author keywords

Drug target; Mucin; Oligosaccharide; Parasite; Synthesis; Trans sialidase

Indexed keywords

DISACCHARIDE; GLYCAN DERIVATIVE; MUCIN; SIALIDASE; TETRASACCHARIDE; THIOGLYCOSIDE;

ARTICLE; CELL SURFACE; CONTROLLED STUDY; GLYCOSYLATION; NONHUMAN; SIALYLATION; SYNTHESIS; TRYPANOSOMA CRUZI;

EID: 51149108304     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078249     Document Type: Article

References (39)

1. http://www.who.int/topics/chagas_disease/en/.
2. Spiro, R. G. Glycobiology 2002, 12, 43R.
3. Buscaglia, C. A.; Campo, V. A.; Frasch, A. C. C.; DiNoia, J. M. Nature Rev. Microbiol. 2006, 4, 229.
4. (a) Schenkman, S.; Jiang, M.-S.; Hart, G. W.; Nussenzweig, V. Cell 1991, 65, 1117.
5. (b) Cross, G. A. M.; Takle, G. B. Annu. Rev. Microbiol. 1993, 47, 385; and citations thereof.
6. Ferguson, M. A. J.; Brimacombe, J. S.; Cottaz, S.; Field, R. A.; Guther, L. S.; Homans, S. W.; McConville, M. J.; Mehlert, A.; Milne, K. G.; Ralton, J. E.; Roy, Y. A.; Schneider, P.; Zitzmann, N. Parasitology 1994, 108, S45.
7. For instance, see: (a) Damager, I.; Buchini, S.; Amaya, M. F.; Buschiazzo, A.; Alzari, P.; Frasch, A. C.; Watts, A.; Withers, S. G. Biochemistry 2008, 47, 3507.
8. (b) Blume, A.; Neubacher, B.; Thiem, J.; Peters, T. Carbohydr. Res. 2007, 342, 1904.
9. (c) Amaya, M. F.; Watts, A. G.; Damager, I.; Wehenkel, A.; Nguyen, T.; Buschiazzo, A.; Paris, G.; Frasch, A. C.; Withers, S. G.; Alzari, P. M. Structure 2004, 12, 775.
10. (d) Haselhorst, T.; Wilson, J. C.; Liakatos, A.; Kiefel, M. J.; Dyason, J. C.; von Itzstein, M. Glycobiology 2004, 14, 895.
11. (e) Watts, A. G.; Damager, I.; Amaya, M. L.; Buschiazzo, A.; Alzari, P.; Frasch, A. C.; Withers, S. G. J. Am. Chem. Soc. 2003, 125, 7532.
12. For representative examples, see: (a) Agusti, R.; Giorgi, M. E.; de Lederkremer, R. M. Carbohydr. Res. 2007, 342, 2465.
13. (b) Kroeger, L.; Scudlo, A.; Thiem, J. Adv. Synth. Catal. 2006, 348, 1217.
14. (c) Neubacher, B.; Schmidt, D.; Ziegelmuller, P.; Thiem, J. Org. Biomol. Chem. 2005, 3, 1551.
15. (d) Turnbull, W. B.; Harrison, J. A.; Karma, K. P. R.; Schenkman, S.; Field, R. A. Tetrahedron 2002, 58, 3207.
16. (e) Singh, S.; Scigelova, M.; Hallberg, M. L.; Howarth, O. W.; Schenkman, S.; Crout, D. H. G. Chem. Commun. 2000, 1013.
17. (f) Probert, M. A.; Milton, M. J.; Harris, R.; Schenkman, S.; Brown, J. M.; Homans, S. W.; Field, R. A. Tetrahedron Lett. 1997, 38, 5861.
18. Harrison, J. A.; Kartha, K. P. R.; Turnbull, W. B.; Scheuerl, S. L.; Naismith, J. H.; Schenkman, S.; Field, R. A. Bioorg. Med. Chem. Lett. 2001, 11, 141.
19. (a) Harris, R.; Kiddle, G. R.; Field, R. A.; Milton, M. J.; Ernst, B.; Magnani, J. L.; Homans, S. W. J. Am. Chem. Soc. 1999, 121, 2546.
20. (b) Milton, M. J.; Harris, R.; Probert, M. A.; Field, R. A.; Homans, S. W. Glycobiology 1998, 8, 147.
21. Islam, T.; von Itzstein, M. Adv. Chem. Biochem. 2008, 61, 292.
22. Neres, J.; Bryce, R. A.; Douglas, K. T. Drug Discov. Today 2008, 13, 110.
23. For instance, see: (a) Agusti, R.; Giorgi, M. E.; Mendoza, V. M.; Gallo-Rodriguez, C.; de Lederkremer, R. M. Bioorg. Med. Chem. 2007, 15, 2611.
24. (b) Mendoza, V. M.; Agusti, R.; Gallo-Rodriguez, C.; de Lederkremer, R. M. Carbohydr. Res. 2006, 341, 1488.
25. (c) Agusti, R.; Mendoza, V. M.; Gallo-Rodriguez, C.; de Lederkremer, R. M. Tetrahedron: Asymmetry 2005, 16, 541; and references cited therein.
26. Campo, V. L.; Carvalho, I.; Allman, S.; Davis, B. G.; Field, R. A. Org. Biomol. Chem. 2007, 5, 2645.
27. Previato, J. O.; Jones, C.; Xavier, M. T.; Wait, R.; Travassos, L. R.; Parodi, A.; Mendonca-Previato, L. J. Biol. Chem. 1995, 270, 7241.
28. ( 15) Bongat, A. F. G.; Demchenko, A. V. Carbohydr. Res. 2007, 342, 374.
29. The studies reported herein have been conducted in parallel with efforts that replace the reducing terminal N-acetyl-glucosamine unit with mannose, which offers more straightforward entry to an α-linked amino acid-glycan linkage.
30. Byramova, N. E.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1983, 124, C8.
31. (a) Doboszewski, B.; Zamojski, A. Carbohydr. Res. 1984, 132, 29.
32. (b) Nepogodiev, S. A.; Backinowsky, L. V.; Grzeszczyk, B.; Zamojski, A. Carbohydr. Res. 1994, 254, 43.
33. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
34. Fujiwara, T.; Arai, K. Carbohydr. Res. 1980, 87, 11.
35. (a) Schmidt, R. R.; Behrendt, M.; Toepfer, A. Synlett 1990, 694.
36. (b) Braccini, I.; Derouet, C.; Esnault, J.; Herve du Penhoat, C.; Mallet, J.-M.; Michon, V.; Sinay, P. Carbohydr. Res. 1993, 246, 23.
37. In the parallel series with a mannose at the reducing terminus, the corresponding coupling gave complete β-stereocontrol albeit in lower yield (54%).
38. +: 822.2461; found: 822.2487.
39. Winans, K. A.; King, D. S.; Rao, V. R.; Bertozzi, C. R. Biochemistry 1999, 38, 11700.