Probing the lactose·GM3 carbohydrate - Carbohydrate interaction with glycodendrimers

Organic Letters

Volumn 11, Issue 3, 2009, Pages 559-562

  Seah, Nicole ^a   Santacroce, Paul V ^a   Basu, Amit ^a  

^a BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; DENDRIMER; GANGLIOSIDE GM3; GLYCOCONJUGATE; LACTOSE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CARBOHYDRATES; DENDRIMERS; G(M3) GANGLIOSIDE; GLYCOCONJUGATES; LACTOSE; MOLECULAR STRUCTURE;

EID: 60849123781     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802613r     Document Type: Article

References (41)

1. (a) For a special issue dedicated to CCI, see: Glycoconjugate J. 2004, 21 (issue 3-4).
2. (b) Bovin, N. V. Biochemistry (Moscow) 1996, 61, 694-704.
3. (c) Rojo, J.; Morales, J. C.; Penadés, S. Top. Curr. Chem. 2002, 218, 45-92.
4. (d) Spillman, D.; Burger, M. M. Carbohydrate-Carbohydrate Interactions; Wiley-VCH: New York, 2000; Vol. 2.
5. (a) Kojiraa, N.; Shiota, M.; Sadahira, Y.; Handa, K.; Hakomori, S. J. Biol. Chem. 1992, 267, 17264-17270.
6. (b) Kojima, N.; Hakomori, S. I. J. Biol. Chem. 1991, 266, 17552-17558.
7. Otsuji, E.; Park, Y. S.; Tashiro, K.; Kojima, N.; Toyokuni, T.; Hakomori, S. Int. J. Oncol. 1995, 6, 319-327.
8. Iwabuchi, K.; Yamamura, S.; Prinetti, A.; Handa, K.; Hakomori, S. J. Biol. Chem. 1998, 273, 9130-9138.
9. (a) Brockman, H. Curr. Opin. Struct. Biol. 1999, 9, 438-443.
10. (b) Brown, R. E.; Brockman, H. L. Methods Mol. Biol. 2007, 398, 41-58.
11. (a) Matsuura, K.; Kobayashi, K. Glycoconjugate J. 2004, 21, 139-148.
12. (b) Matsuura, K.; Kitakouji, H.; Oda, R.; Morimoto, Y.; Asano, H.; Ishida, H.; Kiso, M.; Kitajima, K.; Kobayashi, K. Langmuir 2002, 18, 6940-6945.
13. (c) Santacroce, P. V.; Basu, A. Glycoconjugate J. 2004, 21, 89-95.
14. (d) Santacroce, P. V.; Basu, A. Angew. Chem., Int. Ed. 2003, 42, 95-98.
15. (a) Matsuura, K.; Kitakouji, H.; Sawada, N.; Ishida, H.; Kiso, M.; Kitajima, K.; Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 7406-7407.
16. (b) Matsuura, K.; Oda, R.; Kitakouji, H.; Kiso, M.; Kitajima, K.; Kobayashi, K. Biomacromolecules 2004, 5, 937-941.
17. (a) Rockendorf, N.; Lindhorst, T. K. Top. Curr. Chem. 2001, 217, 201-238.
18. (b) Cloninger, M. J. Curr. Opin. Chem. Biol. 2002, 6, 742-748.
19. (c) Roy, R. Trends Glycosci. Glycotechnol. 2003, 15, 291-310.
20. (a) Lindhorst, T. K.; Kieburg, C. Angew. Chem., Int. Ed. 1996, 35, 1953-1956.
21. (b) Andre, S.; Onega, P. J. C.; Perez, M. A.; Roy, R.; Gabius, H. J. Glycobiology 1999, 9, 1253-1261.
22. (c) Woller, E. K.; Walter, E. D.; Morgan, J. R.; Singel, D. J.; Cloninger, M. J. J. Am. Chem. Soc. 2003, 125, 8820-8826.
23. (d) Wolfenden, M. L.; Cloninger, M. J. Bioconjugate Chem. 2006, 17, 958-966.
24. (a) Samuelson, L. E.; Sebby, K. B.; Walter, E. D.; Singel, D. J.; Cloninger, M. J. Org. Biomol. Chem. 2004, 2, 3075-3079.
25. (b) Mangold, S. L.; Morgan, J. R.; Strohmeyer, G. C.; Gronenborn, A. M.; Cloninger, M. J. Org. Biomol. Chem. 2005, 3, 2354-2358.
26. (c) Schlick, K. H.; Udelhoven, R. A.; Strohmeyer, G. C.; Cloninger, M, J. Mol. Pharm. 2005, 2, 295-301.
27. (d) Wolfenden, M. L.; Cloninger, M. J. J. Am. Chem. Soc. 2005, 127, 12168-12169.
28. (e) Mangold, S. L.; Cloninger, M. J. Org. Biomol. Chem. 2006, 4, 2458-2465.
29. A complete list of all glycodendrimers prepared, along with characterization information, is found in Supporting Information.
30. 32, 7.81 ± 0.81; P-G4, 8.07 ± 0.31
31. 6c,d These lower Δπ values arise as a consequence of the lack of intrinsic surface activity of the glycodendrimers, which do not non-specifically insert into the monolayer.
32. (a) Gestwicki, J. E.; Cairo, C. W.; Strong, L. E.; Oetjen, K. A.; Kiessling, L. L. J. Am. Chem. Soc. 2002, 124, 14922-14933.
33. (b) Mammen, M.; Choi, S. K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2755-2794.
34. While a 50% GM3 monolayer has a higher GM3 content than would be found on the cell surface, it should be noted that the percentage of glycolipid in a lipid raft can be significantly higher: Grauby-Heywang, C.; Turlet, J.-M. Chem. Phys. Lipids 2006, 139, 68-76.
35. 30 over pure water for a 50% GM3 monolayer is 8.5 mN/m.
36. 30, Δπ = 8.6 ± 0.4.
37. Kojima, N.; Hakomori, S. J. Biol. Chem. 1989, 264, 20159-20162.
38. (a) Probst, W.; Mobius, D.; Rahmann, H. Cell. Mol. Neurobiol. 1984, 4, 157-176.
39. (b) Sonnino, S.; Mauri, L.; Chigorno, V.; Prinetti, A. Glycobiology 2007, 17, 1R-13R.
40. Rojo, J.; Diaz, V.; de la Fuente, J. M.; Segura, I.; Barrientos, A. G.; Riese, H. H.; Bemad, A.; Penades, S. ChemBioChem 2004, 5, 291-297.
41. Tomalia, D. A.; Reyna, L. A.; Svenson, S. Biochem. Soc. Trans. 2007, 35, 61-67.