Synthesis and molecular recognition studies of the HNK-1 trisaccharide and related oligosaccharides. the specificity of monoclonal anti-HNK-1 antibodies as assessed by surface plasmon resonance and STD NMR

Journal of the American Chemical Society

Volumn 134, Issue 1, 2012, Pages 426-435

  Tsvetkov, Yury E ^a   Burg Roderfeld, Monika ^b   Loers, Gabriele ^c   Ardá, Ana ^d   Sukhova, Elena V ^a   Khatuntseva, Elena A ^a   Grachev, Alexey A ^a   Chizhov, Alexander O ^a   Siebert, Hans Christian ^b   Schachner, Melitta ^c   Jiménez Barbero, Jesús ^d   Nifantiev, Nikolay E ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b JUSTUS LIEBIG UNIVERSITY   (Germany)

^c UNIVERSITY MEDICAL CENTER HAMBURG EPPENDORF   (Germany)

^d CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY BINDING; AUTOANTIBODIES; CARBOHYDRATE DERIVATIVES; CARBOHYDRATE SPECIFICITY; GLUCURONIC ACIDS; N-ACETYLGLUCOSAMINE; NATURAL KILLER CELLS; PENTASACCHARIDES; PERIPHERAL NERVE REGENERATION; SATURATION-TRANSFER DIFFERENCES; SYNAPTIC PLASTICITY;

ANTIGENS; CARBOHYDRATES; GLUCOSE; MAMMALS; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; OLIGOSACCHARIDES; PLASMONS; SURFACE PLASMON RESONANCE;

ANTIBODIES;

BIOTIN; CARBOHYDRATE; GLUCURONIC ACID; GLYCOSIDE; MONOCLONAL ANTIBODY; OLIGOSACCHARIDE; PENTASACCHARIDE; TRISACCHARIDE;

ANTIGEN BINDING; ARTICLE; GUILLAIN BARRE SYNDROME; MOLECULAR RECOGNITION; NATURAL KILLER CELL; NERVE CELL PLASTICITY; NERVE REGENERATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SURFACE PLASMON RESONANCE; SYNTHESIS;

ANTIBODIES, MONOCLONAL; ANTIBODY SPECIFICITY; ANTIGENS, CD57; BIOTIN; CARBOHYDRATE SEQUENCE; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; SURFACE PLASMON RESONANCE;

EID: 84855671983     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2083015     Document Type: Article

References (58)

1. Chou, D. K. H.; Ilyas, A. A.; Evans, J. E.; Costello, C.; Quarles, R. H.; Jungalwala, F. B. J. Biol. Chem. 1986, 261, 11717-11725
2. Voshol, H.; van Zuylen, C. W. E. M.; Orberger, G.; Vliegenthart, J. F. G.; Schachner, M. J. Biol. Chem. 1996, 271, 22957-22960
3. Martini, R.; Xin, Y.; Schmitz, B.; Schachner, M. Eur. J. Neurosci. 1992, 4, 628-639
4. Martini, R.; Schachner, M.; Brushart, T. M. J. Neurosci. 1994, 14, 7180-7191
5. Schachner, M.; Martini, R.; Hall, H.; Orberger, G. Prog. Brain Res. 1995, 105, 183-188
6. Eberhardt, K. A.; Irintchev, A.; Al-Majed, A. A.; Simova, O.; Brushart, T. M.; Gordon, T.; Schachner, M. Exp. Neurol. 2006, 198, 500-510
7. Simova, O.; Irintchev, A.; Mehanna, A.; Liu, J.; Dihné, M.; Bächle, D.; Sewald, N.; Loers, G.; Schachner, M. Ann. Neurol. 2006, 60, 430-437
8. Irintchev, A.; Lee, H.; Wu, M. M.; Zhu, H.; Feng, Y. P.; Liu, Y. S.; Bernreuther, C.; Loers, G.; You, S. W.; Schachner, M. Mol. Ther. 2011, in press.
9. Kleene, R.; Schachner, M. Nat. Rev. Neurosci. 2004, 5, 195-208
10. Nakano, T.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1993, 243, 43-69
11. Isogai, Y.; Ishida, H.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1996, 15, 1001-1026
12. Isogai, Y.; Ishida, H.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1996, 15, 1119-1137
13. Chevalier, R.; Colsch, B.; Afonso, C.; Baumann, N.; Tabet, J.-C.; Mallet, J.-M. Tetrahedron 2006, 62, 563-577
14. Ding, Y.; Fukuda, M.; Hindsgaul, O. Bioorg. Med. Chem. Lett. 1998, 8, 1903-1908
15. Kononov, L. O.; Kornilov, A. V.; Sherman, A. A.; Zyryanov, E. V.; Zatonsky, G. V.; Shashkov, A. S.; Nifantiev, N. E. Russ. J. Bioorg. Chem. 1998, 24, 537-550
16. Kornilov, A. V.; Sherman, A. A.; Kononov, L. O.; Shashkov, A. S.; Nifantiev, N. E. Carbohydr. Res. 2000, 329, 717-730
17. Sukhova, E. V.; Dubrovskii, A. V.; Tsvetkov, Y. E.; Nifantiev, N. E. Russ. Chem. Bull. 2007, 56, 1655-1670
18. Bastide, L.; Priem, B.; Fort, S. Carbohydr. Res. 2011, 346, 348-351
19. Gutiérrez Gallego, R.; Jiménez Blanco, J.; Thijssen-Zuylen, C. W. E. M.; Gotfredsen, C. H.; Voshol, H.; Duus, J. O.; Schachner, M.; Vliegenthart, J. F. G. J. Biol. Chem. 2001, 276, 30834-30844
20. Barthel, S. R.; Wiese, G. K.; Cho, J.; Opperman, M. J.; Hays, D. L.; Siddiqui, J.; Pienta, K. J.; Furie, B.; Dimitroff, C. J. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 19491-19496
21. Gooi, H. C.; Feizi, T.; Kapadia, A.; Knowles, B. B.; Solter, D.; Evans, M. J. Nature 1981, 292, 156-158
22. Andressen, C.; Arnhold, S.; Mai, J. K. Anat. Embryol. 1997, 197, 209-215
23. Wang, J.-W.; Ambros, R. A.; Weber, P. B.; Rosano, T. G. Cancer Res. 1995, 55, 3654-3658
24. Sherman, A. A.; Yudina, O. N.; Mironov, Y. V.; Sukhova, E. V.; Shashkov, A. S.; Menshov, V. M.; Nifantiev, N. E. Carbohydr. Res. 2001, 336, 13-46
25. Schmitz, B.; Schachner, M.; Ito, Y.; Nakano, T.; Ogawa, T. Glycocon. J. 1994, 11, 345-352
26. Tokuda, A.; Ariga, T.; Isogai, Y.; Komba, S.; Kiso, M.; Hasegawa, A.; Tai, T.; Yu, R. K. J. Carbohydr. Chem. 1998, 17, 535-546
27. Higson, A. P.; Tsvetkov, Y. E.; Ferguson, M. A. J.; Nikolaev, A. V. J. Chem. Soc., Perkin Trans. 1 1998, 2587-2596
28. Kornilov, A. V.; Sukhova, E. V.; Nifantiev, N. E. Carbohydr. Res. 2001, 336, 309-313
29. Garegg, P. J.; Kvarnström, I.; Niklasson, A.; Niklasson, G.; Svensson, S. C. T. J. Carbohydr. Chem. 1993, 12, 933-954
30. Kornilov, A. V.; Kononov, L. O.; Zatonskii, G. V.; Shashkov, A. S.; Nifantiev, N. E. Russ. J. Bioorg. Chem. 1997, 23, 597-607
31. Liao, L.; Auzanneau, F.-I. Org. Lett. 2003, 5, 2607-2610
32. Liao, L.; Auzanneau, F.-I. J. Org. Chem. 2005, 70, 6265-6273
33. Byramova, N. E.; Ovchinnikov, M. V.; Backinowsky, L. V.; Kochetkov, N. K. Carbohydr. Res. 1983, 124, C8-C11
34. Mukherjee, A.; Palcic, M. M.; Hindsgaul, O. Carbohydr. Res. 2000, 326, 1-21
35. Duverger, E.; Frison, N.; Roche, A.-C.; Monsigny, M. Biochimie 2003, 85, 167-179
36. Kobayashi, Y.; Nakamura, H.; Sekiguchi, T.; Takanami, R.; Murata, T.; Usui, T.; Kawagushi, H. Anal. Biochem. 2005, 336, 87-93
37. Suda, Y.; Arano, A.; Fukui, Y.; Koshida, S.; Wakao, M.; Nashimura, T.; Kusumoto, S.; Sobel, M. Bioconjugate Chem. 2006, 17, 1125-1135
38. Murthy, B. N.; Voelcker, N. H.; Jayaraman, N. Glycobiology 2006, 16, 822-832
39. Collot, M.; Sendid, B.; Fievez, A.; Savaux, C.; Standaert-Vitse, A.; Tabouret, M.; Drucbert, A. S.; Danzé, P. M.; Poulain, D.; Mallet, J.-M. J. Med. Chem. 2008, 51, 6201-6210
40. Linman, M. J.; Taylor, J. D.; Yu, H.; Chen, X.; Cheng, Q. Anal. Chem. 2008, 80, 4007-4013 and references sited therein
41. Mann, D. A.; Kanai, M.; Maly, D. J.; Kiessling, L. L. J. Am. Chem. Soc. 1998, 120, 10575-10582
42. Liang, P.-H.; Wang, S.-K.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 11177-11184
43. Zhu, J.; Wan, Q.; Danishefsky, S. J. Tetrahedron Lett. 2009, 50, 712-714
44. Karamanska, R.; Clarke, J.; Blixt, O.; MacRae, J. I.; Zhang, J. Q.; Crocker, P. R.; Laurent, N.; Wright, A.; Flitsch, S. L.; Russel, D. A.; Field, R. A. Glycoconjugate J. 2008, 25, 69-74
45. Herzner, H.; Kunz, H. Carbohydr. Res. 2007, 342, 541-557
46. Meyer, B.; Peters, T. Angew. Chem., Int. Ed. 2003, 42, 864-890
47. Canales, A.; Matesanz, R.; Gardner, N.; Andreu, J. M.; Paterson, I.; Díaz, F.; Jiménez-Barbero, J. Chem.-Eur. J. 2008, 14, 7557-69
48. Oberli, M. A.; Tamborrini, M.; Tsai, Y.-H.; Werz, D. B.; Horlacher, T.; Adibekian, A.; Gauss, D.; Moller, H. M.; Pluschke, G.; Seeberger, P. H. J. Am. Chem. Soc. 2010, 132, 10239-10241
49. Groves, P. Magn. Reson. Chem. 2007, 45, 745-748
50. Mayer, M.; Meyer, B. J. Am. Chem. Soc. 2001, 123, 6108-6111
51. Bernardi, A.; Arosio, D.; Potenza, D.; Sanchez-Medina, I.; Mari, S.; Cañada, F. J.; Jimenez-Barbero, J. Chem.-Eur. J. 2004, 10, 4395-4405
52. Johnson, M. A.; Pinto, B. M. Carbohydr. Res. 2004, 339, 907-928
53. Groves, P.; Rasmussen, M.; Molero, M. D.; Samain, E.; Cañada, F. J.; Driguez, H.; Jiménez-Barbero, J. Glycobiology 2004, 14, 451-456
54. Bhunia, A. J. Am. Chem. Soc. 2010, 132, 96-105
55. Kruse, J.; Mailhammer, R.; Wernecke, H.; Faissner, A.; Sommer, I.; Goridis, C.; Schachner, M. Nature 1984, 311, 153-155
56. Voshol, H.; van Zuylen, C. W.; Orberger, G.; Vliegenthart, J. F.; Schachner, M. J. Biol. Chem. 1996, 271, 22957-22960
57. Hall, H.; Deutzmann, R.; Timpl, R.; Vaughan, L.; Schmitz, B.; Schachner, M. Eur. J. Biochem. 1997, 246, 233-242
58. Saghatelyan, A. K.; Gorissen, S.; Meigel, I.; Mosbacher, J.; Kaupmann, K.; Bettler, B.; Kornilov, A. V.; Nifantiev, N. E.; Schachner, M.; Dityatev, A. Mol. Cell. Neurosci. 2003, 24, 271-282