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Pure Appl. Chem., 1989, Vol. 61, No. 7, pp. 1171-1180

http://dx.doi.org/10.1351/pac198961071171

Antibody combining sites and oligosaccharide determinants studied by competitive binding, sequencing and X-ray crystallography

D. R. Bundle

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  • Moore Christopher J., Auzanneau France-Isabelle: Understanding the Recognition of Lewis X by Anti-Lex Monoclonal Antibodies. J. Med. Chem. 2013, 56, 8183. <http://dx.doi.org/10.1021/jm401304h>
  • Shi Yun, Pinto B. Mario: Molecular dynamics simulations of carbohydrate-mimetic haptens in complex with a complementary anti-carbohydrate antibody. Carbohydrate Research 2012, 358, 89. <http://dx.doi.org/10.1016/j.carres.2012.05.024>
  • Hossany B. Rehana, Johnston Blair D., Wen Xin, Borrelli Silvia, Yuan Yue, Johnson Margaret A., Pinto B. Mario: Design, synthesis, and immunochemical characterization of a chimeric glycopeptide corresponding to the Shigella flexneri Y O-polysaccharide and its peptide mimic MDWNMHAA. Carbohydrates Research 2009, 344, 1412. <http://dx.doi.org/10.1016/j.carres.2009.03.029>
  • Zhuo, Liu Qian, Wang, Ren, Wang: Volumetric and Viscosity Properties of Monosaccharides in Aqueous Amino Acid Solutions at 298.15 K. J Chemical & Engineering Data 2006, 51, 919. <http://dx.doi.org/10.1021/je050412t>
  • McGavin Robert S., Gagne Rod A., Chervenak Mary C., Bundle David R.: The design, synthesis and evaluation of high affinity macrocyclic carbohydrate inhibitors. Org Biomol Chem 2005, 3, 2723. <http://dx.doi.org/10.1039/b416105j>
  • Hossany Rehana B, Johnson Margaret A, Eniade Adewale A, Pinto B.Mario: Synthesis and immunochemical characterization of protein conjugates of carbohydrate and carbohydrate-mimetic peptides as experimental vaccines. biorg med chem 2004, 12, 3743. <http://dx.doi.org/10.1016/j.bmc.2004.03.075>
  • Vyas N. K., Vyas M. N., Chervenak M. C., Bundle D. R., Pinto B. M., Quiocho F. A.: Structural basis of peptide-carbohydrate mimicry in an antibody-combining site. Proceedings of the National Academy of Sciences 2003, 100, 15023. <http://dx.doi.org/10.1073/pnas.2431286100>
  • Zhang Ping, Appleton Judith, Ling Chang-Chun, Bundle David R: Synthesis of disaccharide congeners of the Trichinella spiralis glycan and binding site mapping of two monoclonal antibodies. Can J Chem 2002, 80, 1141. <http://dx.doi.org/10.1139/v02-117>
  • Kowal Czeslawa, Weinstein Arthur, Diamond Betty: Molecular mimicry between bacterial and self antigen in a patient with systemic lupus erythematosus. Eur J Immunol 1999, 29, 1901. <http://dx.doi.org/10.1002/(SICI)1521-4141(199906)29:06<1901::AID-IMMU1901>3.0.CO;2-L>
  • Sujino Keiko, Malet Carles, Hindsgaul Ole, Palcic Monica M.: Acceptor hydroxyl group mapping for calf thymus α-(1 → 3) - galactosyltransferase and enzymatic synthesis of analogs. Carbohydrates Research 1997, 305, 483. <http://dx.doi.org/10.1016/S0008-6215(97)00268-1>
  • Bernardi Anna, Raimondi Laura, Zanferrari Domenico, Venable Richard M., Bizik Frantisek, Henderson Terry J., Egan William, Kreis Uwe C., Varma Vikram, Pinto B.Mario: Conformational analysis of saccharides with Monte Carlo/stochastic dynamics simulations. Journal of Molecular Structure: THEOCHEM 1997, 395-396, 361. <http://dx.doi.org/10.1016/S0166-1280(96)04541-1>
  • Asam Michael R., Glish Gary L.: Tandem mass spectrometry of alkali cationized polysaccharides in a quadrupole ion trap. j am soc mass spectrom 1997, 8, 987. <http://dx.doi.org/10.1016/S1044-0305(97)00124-4>
  • Fujimoto Takako, Yanagihara Ryoji, Kobayashi Kenji, Aoyama Yasuhiro: C-H....PI. Hydrogen Bonding between Electron-Rich Benzene Rings and Polarized C-H Bonds: Selectivity in the Complexation of Highly Hydrophilic Guest Molecules with Calix(4)resorcarene Hosts in Water. Bull Chem Soc Jpn 1995, 68, 2113. <http://dx.doi.org/10.1246/bcsj.68.2113>
  • Yanagihara Ryoji, Aoyama Yasuhiro: Enhanced sugar-binding ability of deprotonated calix[4]resorcarene in water: Balance of CH-π interaction and hydrophobic effect. Tetrahetron Lett 1994, 35, 9725. <http://dx.doi.org/10.1016/0040-4039(94)88370-X>
  • Ellervik Ulf, Magnusson Göran: Calculated conformations of sialyl-Lex- and sialyl-Lea-lactones. biorg med chem 1994, 2, 1261. <http://dx.doi.org/10.1016/S0968-0896(00)82077-5>
  • Rose D. R., Przybylska M., To R. J., Kayden C. S., Vorberg E., Young N. M., Bundle D. R., Oomen R. P.: Crystal structure to 2.45 Å resolution of a monoclonal Fab specific for the Brucella A cell wall polysaccharide antigen. Protein Sci 1993, 2, 1106. <http://dx.doi.org/10.1002/pro.5560020705>
  • Auzanneau France-Isabelle, Hanna H.Rizk, Bundle David R.: The synthesis of chemically modified disaccharide derivatives of the Shigella flexneri Y polysaccharide antigen. Carbohydrates Research 1993, 240, 161. <http://dx.doi.org/10.1016/0008-6215(93)84181-5>
  • Auzanneau France-Isabelle, Bundle David R.: Synthesis of chlorodeoxy trisaccharides related to the Shigella flexneri Y polysaccharide. Carbohydrates Research 1993, 247, 195. <http://dx.doi.org/10.1016/0008-6215(93)84252-2>
  • Gudmundsson Britt-Marie E., Martin Young N., Oomen Raymond P.: Characterisation of residues in antibody binding sites by chemical modification of surface-adsorbed protein combined with enzyme immunoassay. J  Immunol Methods 1993, 158, 215. <http://dx.doi.org/10.1016/0022-1759(93)90217-U>
  • Otsuki Jun-ichi, Kobayashi Kenji, Toi Hiroo, Aoyama Yasuhiro: Oligosaccharide-Peptide Interaction. Binding of Maltodextrin to Trp-Trp via Sugar-Bisindole Intercalation. Tetrahetron Lett 1993, 34, 1945. <http://dx.doi.org/10.1016/S0040-4039(00)91970-1>
  • Spijker Nynke M., Slief Jan-Willem, Van Boeckel Constant A. A.: Synthesis of Modified Di- and Trisaccharide Fragments of N-Glycoproteins. J Carbohydr Chem 1993, 12, 1017. <http://dx.doi.org/10.1080/07328309308020115>
  • Nagai Yoshiro, Kobayashi Kenji, Toi Hiroo, Aoyama Yasuhiro: Stabilization of Sugar-Boronic Esters of Indolylboronic Acid in Water via Sugar-Indole Interaction: A Notable Selectivity in Oligosaccharides. Bull Chem Soc Jpn 1993, 66, 2965. <http://dx.doi.org/10.1246/bcsj.66.2965>
  • Kihlberg Jan, Bundle David R.: The synthesis of antibody binding-site probes: a hexasaccharide and two pentasaccharides related to the Brucella A antigen and prepared by in situ activation of thioglycosides with bromine. Carbohydrates Research 1992, 216, 67. <http://dx.doi.org/10.1016/0008-6215(92)84151-H>
  • Motomura Tadahiro, Aoyama Yasuhiro: Multiple Electrostatic Interaction of Polycationic Chitosan Oilgomers with Nucleic Acids: Polyamine Promoted Stabilization of the A-Form of RNA and DNA in Aqueous Solutions. Bull Chem Soc Jpn 1992, 65, 1755. <http://dx.doi.org/10.1246/bcsj.65.1755>
  • Kihlberg Jan, Eichler Eva, Bundle David R.: The design and synthesis of antibody binding site probes: three pentasaccharide analogues of the Brucella A antigen prepared by activation in situ of thioglycosides with bromine. Carbohydrates Research 1991, 211, 59. <http://dx.doi.org/10.1016/0008-6215(91)84146-6>
  • RIVERA-SAGREDO Alfonso, SOLIS Dolores, DIAZ-MAURINO Teresa, JIMENEZ-BARBERO Jesus, MARTIN-LOMAS Manuel: Studies on the molecular recognition of synthetic methyl beta-lactoside analogs by ricin, a cytotoxic plant lectin. Eur J Biochem 1991, 197, 217. <http://dx.doi.org/10.1111/j.1432-1033.1991.tb15902.x>
  • SIGURSKJOLD Bent W., ALTMAN Eleonora, BUNDLE David R.: Sensitive titration microcalorimetric study of the binding of Salmonella O-antigenic oligosaccharides by a monoclonal antibody. Eur J Biochem 1991, 197, 239. <http://dx.doi.org/10.1111/j.1432-1033.1991.tb15904.x>
  • Meikle Peter J, Bundle David R: Preparation of polysaccharide-enzyme conjugates for competitive binding assays. Glycoconjugate J 1990, 7, 207. <http://dx.doi.org/10.1007/BF01050604>
  • Vorberg Ewald, Bundle David R.: Carbohydrate-enzyme conjugates for competitive EIA. J  Immunol Methods 1990, 132, 81. <http://dx.doi.org/10.1016/0022-1759(90)90401-G>