Design, synthesis, and immunochemical characterization of a chimeric glycopeptide corresponding to the Shigella flexneri Y O-polysaccharide and its peptide mimic MDWNMHAA

Carbohydrate Research

Volumn 344, Issue 12, 2009, Pages 1412-1427

  Hossany, B Rehana ^a   Johnston, Blair D ^a   Wen, Xin ^b   Borrelli, Silvia ^a   Yuan, Yue ^a   Johnson, Margaret A ^a   Pinto, B Mario ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

^b NANKAI UNIVERSITY   (China)

Author keywords

Carbohydrate mimetic peptide; Glycopeptide chimera; Immunochemistry; Molecular modeling; Shigella flexneri Y O polysaccharide; Synthesis

Indexed keywords

ACTIVE SITE; AUTODOCK; BEST MODEL; BINDING AFFINITIES; BOUND WATER MOLECULES; C-TERMINUS; COGNATE LIGANDS; GLYCOPEPTIDE CHIMERA; GLYCOPEPTIDES; IMMUNOCHEMISTRY; LIPOPOLYSACCHARIDES; O-POLYSACCHARIDE; PENTASACCHARIDES; PEPTIDE MIMICS; SHIGELLA FLEXNERI; SHIGELLA FLEXNERI Y O-POLYSACCHARIDE; SOLID-PHASE; SYNTHESIS; X RAY CRYSTAL STRUCTURES;

AMINES; BINDING ENERGY; BIOCHEMISTRY; CARBOHYDRATES; LIGANDS; MOLECULAR MODELING; MOLECULES; MONOCLONAL ANTIBODIES; PEPTIDES; POLYSACCHARIDES;

BIOMIMETICS;

ALPHA THIOGLYCOSIDE; BETA THIOGLYCOSIDE; CHIMERIC PROTEIN; GLYCOPEPTIDE; LIPOPOLYSACCHARIDE; LIPOPOLYSACCHARIDE Y; METHIONYLASPARTYLTRYPTOPHYLASPARAGINYLMETHIONYLHISTIDYLALANYLALANINAMIDE; MONOCLONAL ANTIBODY; MONOCLONAL ANTIBODY SYA J6; POLYSACCHARIDE; RHAMNOSE; SYNTHETIC PEPTIDE; UNCLASSIFIED DRUG;

ANTIBODY COMBINING SITE; ARTICLE; BINDING AFFINITY; CRYSTAL STRUCTURE; ENTROPY; IMMUNOCHEMISTRY; MOLECULAR DOCKING; MOLECULAR MIMICRY; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; SHIGELLA FLEXNERI; SOLID; X RAY ANALYSIS;

CARBOHYDRATE SEQUENCE; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; ENZYME-LINKED IMMUNOSORBENT ASSAY; GLYCOPEPTIDES; IMMUNOHISTOCHEMISTRY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; POLYSACCHARIDES, BACTERIAL; SHIGELLA FLEXNERI;

SHIGELLA FLEXNERI;

EID: 68249093093     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.03.029     Document Type: Article

References (52)

1. Grandi G. Trends Biotechnol. 19 (2001) 181-188
2. Jennings H.J. Curr. Top. Microbiol. Immunol. 150 (1990) 97-127
3. Jennings H.J. Adv. Exp. Med. Biol. 228 (1988) 495-550
4. Lee C.J. Mol. Immunol. 24 (1987) 1005-1019
5. Lindberg A.A. Vaccine 17 (1999) S28-36
6. Weintraub A. Carbohydr. Res. 338 (2003) 2539-2547
7. Mc Cool T.L., Harding C.V., Greenspan N.S., and Schreiber J.R. Infect. Immun. 67 (1999) 4862
8. Roy R. Drug Discovery Today: Technol. 1 (2004) 327-336
9. Mond J.J., Lees A., and Snapper C.M. Annu. Rev. Immunol. 13 (1995) 655-692
10. Parker D.C. Annu. Rev. Immunol. 11 (1993) 331-360
11. Gonzalez-Fernandez A., Faro J., and Fernandez C. Vaccine 26 (2008) 292-300
12. Barington T., Gyhrs A., Kristensen K., and Heilmann C. Infect. Immun. 62 (1994) 9-14
13. Peeters C., Tenbergenmeekes A.M., Poolman J.T., Beurret M., Zegers B.J.M., and Rijkers G.T. Infect. Immun. 59 (1991) 3504-3510
14. Johnson M.A., and Pinto B.M. Top. Curr. Chem. 273 (2008) 55-116 and references cited therein
15. Johnson M.A., and Pinto B.M. Aust. J. Chem. 55 (2002) 13-25
16. Borrelli S., Hossany R.B., and Pinto B.M. Clin. Vaccine Immunol. 15 (2008) 1106-1117
17. Borrelli S., Johnson M.A., Hossany R.B., and Findlay S. ACS Symp. Ser. 989 (2007) 335
18. Harris S.L., Craig L., Mehroke J.S., Rashed M., Zwick M.B., Kenar K., Toone E.J., Greenspan N., Auzanneau F.I., MarinoAlbernas J.R., Pinto B.M., and Scott J.K. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 2454-2459
19. Borrelli S., Hossany R.B., Findlay S., and Pinto B.M. Am. J. Immunol. 2 (2006) 73-83
20. Hale T.L. In: Hansler W.J., and Shumman M. (Eds). Topley and Wilson's Microbiology and Microbial Infections (1998), Arnold, London 479-493
21. Vyas N.K., Vyas M.N., Chervenak M.C., Johnson M.A., Pinto B.M., Bundle D.R., and Quiocho F.A. Biochemistry 41 (2002) 13575-13586
22. Vyas N.K., Vyas M.N., Chervenak M.C., Bundle D.R., Pinto B.M., and Quiocho F.A. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 15023-15028
23. Beenhouwer D.O., May R.J., Valadon P., and Scharff M.D. J. Immunol. 169 (2002) 6992-6999
24. Hossany R.B., Johnson M.A., Eniade A.A., and Pinto B.M. Bioorg. Med. Chem. 12 (2004) 3743-3754
25. Horton D., and Wander J.D. In: Pigman W.W., and Horton D. (Eds). The Carbohydrates Vol. 1A (1980), Academic, New York 799
26. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639-1662
27. Auzanneau F.I., Forooghian F., and Pinto B.M. Carbohydr. Res. 291 (1996) 21-41
28. Hoog C., Rotondo A., Johnston B.D., and Pinto B.M. Carbohydr. Res. 337 (2002) 2023-2036
29. Pozgay V. Carbohyd. Res. 235 (1992) 295-302
30. Kartha K.P.R., and Field R.A. Tetrahedron Lett. 38 (1997) 8233-8236
31. Hecht S. Recognition of Carbohydrate Antigens by Antibody Binding Sites. The Carbohydrates (1998), Oxford University, Oxford 370-440
32. Zhu X.M., and Schmidt R.R. Chem. Eur. J. 10 (2004) 875-887
33. Mergler M., and Dick F. J. Pept. Sci. 11 (2005) 650-657
34. Hvidt T., Szarek W.A., and Maclean D.B. Can. J. Chem. 66 (1988) 779-782
35. Sheppeck J.E., Kar H., and Hong H. Tetrahedron Lett. 41 (2000) 5329-5333
36. Cammish L.E., and Kates S.A. In: Chan W.C., and White P.D. (Eds). Fmoc Solid Phase Peptide Synthesis: A Practical Approach (2000), Oxford University, Oxford 277
37. Dourtoglou V., Gross B., Lambropoulou V., and Zioudrou C. Synthesis 7 (1984) 572-574
38. Dourtoglou V., Ziegler J.C., and Gross B. Tetrahedron Lett. 15 (1978) 1269-1272
39. Knorr R., Trzeciak A., Bannwarth W., and Gillessen D. Tetrahedron Lett. 30 (1989) 1927-1930
40. Chan W.C., Bycroft B.W., Evans D.J., and White P.D. J. Chem. Soc., Chem. Commun. (1995) 2209-2210
41. Barlos K., and Gatos D. In: Chan W.C., and White P.D. (Eds). Fmoc Solid Phase Peptide Synthesis: A Practical Approach (2000), Oxford University, Oxford 215-228
42. In: Perrin D.D., and Armarego W.L.F. (Eds). Purification of Laboratory Chemicals. 3rd ed. (1988), Pergamon, London
43. Kaiser E., Colescot R., Bossinge C., and Cook P.I. Anal. Biochem. 34 (1970) 595-598
44. Altman E., and Bundle D.R. Methods Enzymol. 247 (1994) 243-253
45. Bundle D.R., Gidney M.A., Josephson S., and Wessel H.-P. ACS Symp. Ser. 231 (1983) 49-63
46. Bundle D.R. Pure Appl. Chem. 61 (1989) 1171-1180
47. Bundle D.R., Altman E., Auzanneau F.I., Baumann H., Eichler E., and Sigurskjold B.W. In: Bock K., and Clausen H. (Eds). Alfred Benzon Symp. Ser vol. 36 (1994), Munksgaard, Copenhagen 168-181
48. Vyas M.N., Vyas N.K., Meikle P.J., Sinnott B., Pinto B.M., Bundle D.R., and Quiocho F.A. J. Mol. Biol. 231 (1993) 133-136
49. Clark M., Cramer R.D., and Vanopdenbosch N. J. Comput. Chem. 10 (1989) 982-1012
50. Gasteiger J., and Marsili M. Tetrahedron 36 (1980) 3219-3228
51. Gasteiger J., and Marsili M. Org. Magn. Reson. 15 (1981) 353-360
52. Cornell W.D., Cieplak P., Bayly C.I., Gould I.R., Merz K.M., Ferguson D.M., Spellmeyer D.C., Fox T., Caldwell J.W., and Kollman P.A. J. Am. Chem. Soc. 117 (1995) 5179-5197