Synthesis and self-assembly of globotriose derivatives: A model system for studies of carbohydrate-protein interactions

Langmuir

Volumn 18, Issue 7, 2002, Pages 2848-2858

  Svedhem, Sofia ^a   Öhberg, Liselotte ^b,d   Borrelli, Silvia ^c,e   Valiokas, Ramunas ^a   Andersson, Mats ^b,f   Oscarson, Stefan ^b   Svensson, Stefan C T ^a   Liedberg, Bo ^a   Konradsson, Peter ^a  

^a LINKÖPING UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

^c KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

^d ASTRAZENECA R AND D   (Sweden)

^e NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^f Medicarb   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CARBOHYDRATES; CONTACT ANGLE; ELLIPSOMETRY; GONIOMETERS; PROTEINS; SYNTHESIS (CHEMICAL);

ORGANIC FILMS;

SELF ASSEMBLY;

EID: 20244362890     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la015643m     Document Type: Article

References (55)

1. Ulman, A. Chem. Rev. 1996, 96, 1533-1554.
2. (a) Löfås, S.; Johnsson, B. J. Chem. Soc., Chem. Commun. 1990, 1526-1528.
3. (b) Commercially available from Biacore AB, Uppsala, Sweden.
4. Horan, N.; Yen, L.; Isobe, H.; Whitesides, G.M.; Kahne, D. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 11782-11786.
5. Mrksich, M. Chem. Soc. Rev. 2000, 29, 267-273.
6. Varki, A. Glycobiology 1993, 3, 97-130.
7. Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G., Marth, J., Eds. Essentials of Glycobiology; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1999.
8. Kurzehalia, T.V.; Parton, R.G. Curr. Opin. Cell Biol. 1999, 11, 424-431.
9. Evans, S.V.; MacKenzie, C.R. J. Mol. Recognit. 1999, 12, 155-168.
10. Mammen, M.; Choi, S.-K.; Whitesides, G.M. Angew. Chem., Int. Ed. 1998, 37, 2754-2794.
11. Kitov, P.I.; Sadowska, J.M.; Mulvey, G.; Armstrong, G.D.; Ling, H.; Pannu, N.S.; Read, R.J.; Bundle, D.R. Nature 2000, 403, 669-672.
12. Garegg, P.; Hultberg, H. Carbohydr. Res. 1982, 110, 261-266.
13. Magnusson, G.; Nilsson, U.; Ray, A.K.; Taylor, K.G. ACS Symp. Ser. 1993, No. 519, 92-110.
14. Kitov, P.I.; Railton, C.; Bundle, D.R. Carbohydr. Res. 1998, 307, 361-369.
15. Ohlsson, J.; Magnusson, G. Tetrahedron 2000, 56, 9975-9984.
16. Karlsson, K.A. Curr. Opin. Struct. Biol. 1995, 5, 622-635.
17. Nilsson, K.G.I.; Mandenius, C.-F. Bio-Technol. 1994, 12, 1376-1378.
18. Revell, D.J.; Knight, J.R.; Blyth, D.J.; Haines, A.H.; Russell, D.A. Langmuir 1998, 14, 4517-4524.
19. Fritz, M.C.; Hähner, G.; Spencer, N.D.; Bürli, R.; Vasella, A. Langmuir 1996, 12, 6074-6082.
20. Houseman, B.; Mrksich, M. Angew. Chem., Int. Ed. 1999, 38, 782-785.
21. Nyquist, R.M.; Eberhardt, A.S.; Silks, L.A., III; Li, Z.; Yang, X.; Swanson, B.I. Langmuir 2000, 16, 1793-1800.
22. Borrelli, S.; Altmann, K.; Jansson, P.-E.; Lindberg, A.A. Microb. Pathog. 1995, 19, 139-157.
23. Borrelli, S. 1996.
24. Borrelli, S.; Jansson, P.-E.; Lindberg, A.A. Microb. Pathog. 1996, 21, 307-318.
25. Pharmacia, WO90/05303, 1990.
26. Drabowicz, J.; Mikolajczyk, M. Synth Commun. 1980, 32-34.
27. 1H NMR data were in agreement with the characterization by Lebeau, L.; Oudet, P.; Mioskowski, C. Helv. Chim. Acta 1991, 74, 1697-1706.
28. 1H NMR data were in agreement with the characterization by Lebeau, L.; Oudet, P.; Mioskowski, C. Helv. Chim. Acta 1991, 74, 1697-1706.
29. Bannwarth, W.; Knorr, R. Tetrahedron Lett. 1991, 32, 1157-1160.
30. Konda, Y.; Toida, T.; Kaji, E.; Takeda, K.; Harigaya, Y. Carbohydr. Res. 1997, 301, 123-143.
31. Schmidt, R.R. Angew. Chem., Int. Ed. 1986, 25, 212-235.
32. Garegg, P.J.; Konradsson, P.; Kvarnström, I.; Norberg, T.; Svensson, S.C.T.; Wigilius, B. Acta Chem. Scand., Ser. B 1985, 39, 569-577.
33. Lestelius, M.; Liedberg, B.; Tengvall, P. Langmuir 1997, 13, 5900-5908.
34. Valiokas, R.; Svedhem, S.; Svensson, S.C.T.; Liedberg, B. Langmuir 1999, 15, 3390-3394.
35. Atre, S.V.; Liedberg, B.; Allara, D.L. Langmuir 1995, 11, 3882-3893.
36. MacPhail, R.A.; Strauss, H.L.; Snyder, R.G.; Elliger, C.A. J. Phys. Chem. 1984, 88, 334-341.
37. Snyder, R.G.; Strauss, H.L.; Elliger, C.A. J. Phys. Chem. 1982, 86, 5145-5150.
38. R.; Östblom, M.; Svedhem, S.; Svensson, S.C.T.; Liedberg, B. J. Phys. Chem. B 2000, 104, 7565-7569.
39. Bertilsson, L.; Liedberg, B. Langmuir 1993, 9, 141-149.
40. Allara, D.L.; Baca, A.; Pryde, C.A. Macromolecules 1978, 11, 1215-1220.
41. Cummings, M.D.; Ling, H.; Armstrong, G.D.; Brunton, J.L.; Read, R.J. Biochemistry 1998, 37, 1789-1799.
42. Ling, H.; Boodhoo, A.; Hazes, B.; Cummings, M.D.; Armstrong, G.D.; Brunton, J.L.; Read, R.J. Biochemistry 1998, 37, 1777-1788.
43. Svedhem, S.; Hollander, C.-Å.; Shi, J.; Konradsson, P.; Liedberg, B.; Svensson, S.C.T. J. Org. Chem. 2001, 66, 4494-4503.
44. Kasahara, K.; Sanai, Y. Biophys. Chem. 1999, 82, 121-127.
45. Brown, D.A.; London, E. J. Biol. Chem. 2000, 275, 17221-17224.
46. Xavier, R.; Seed, B. Curr. Opin. Immunol. 1999, 11, 265-269.
47. Löfås, S.; Johnsson, B.; Tegendahl, K.; Rönnberg, I. Colloids Surf., B 1993, 1, 83-89.
48. Fritz, J.; Anselmetti, D.; Jarchow, J.; Fernàndez-Busquets, X. J. Struct. Biol. 1997, 119, 165-171.
49. Stenberg, E.; Persson, B.; Roos, H.; Urbaniczky, C. J. Colloid Interface Sci. 1991, 143, 513-526.
50. Liedberg, B.; Lundström, I.; Stenberg, E. Sens. Actuators, B 1993, 11, 63-72.
51. Lahiri, J.; Isaacs, L.; Grzybowski, B.; Carbeck, J.D.; Whitesides, G.M. Langmuir 1999, 15, 7186-7198.
52. Virji, M.; Weiser, J.; Lindberg, A.; Moxon, E. Microb. Pathog. 1990, 9, 441-450.
53. Lind, S.M.; Carlin, N.I.A.; Lindberg, A.A. FEMS Microbiol. Lett. 1985, 28, 45-49.
54. Porter, M.D.; Bright, T.B.; Allara, D.L.; Chidsey, C.E.D. J. Am. Chem. Soc. 1987, 109, 3559-3568.
55. Shi, J.; Hong, B.; Parikh, A.N.; Collins, R.W.; Allara, D.L. Chem. Phys. Lett. 1995, 246, 90-94.