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Pure Appl. Chem., 1991, Vol. 63, No. 4, pp. 473-482

http://dx.doi.org/10.1351/pac199163040473

Carbohydrate-carbohydrate interaction as an initial step in cell recognition

Sen-itiroh Hakomori

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  • Hsieh Hsiao-Wu, Davis Ryan A., Hoch Jessica A., Gervay-Hague Jacquelyn: Two-Step Functionalization of Oligosaccharides Using Glycosyl Iodide and Trimethylene Oxide and Its Applications to Multivalent Glycoconjugates. Chem. Eur. J. 2014, n/a. <http://dx.doi.org/10.1002/chem.201400024>
  • Hsieh Hsiao-Wu, Schombs Matthew W., Gervay-Hague Jacquelyn: Integrating ReSET with Glycosyl Iodide Glycosylation in Step-Economy Syntheses of Tumor-Associated Carbohydrate Antigens and Immunogenic Glycolipids. J. Org. Chem. 2014, 79, 1736. <http://dx.doi.org/10.1021/jo402736g>
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  • Kaptan Engin, Sengezer Inceli Meliha, Sancar Bas Serap: Lectin binding properties of liver, small intestine and tail of metamorphosing marsh frog (Pelophylax ridibundus Pallas 1771). Acta Histochemica 2013, 115, 595. <http://dx.doi.org/10.1016/j.acthis.2013.01.002>
  • Kopitzki Sebastian, Dilmaghani Karim Akbari, Thiem Joachim: Synthesis of benzaldehyde-functionalized LewisX trisaccharide analogs for glyco-SAM formation. Tetrahedron 2013, 69, 10621. <http://dx.doi.org/10.1016/j.tet.2013.10.027>
  • Marradi Marco, Chiodo Fabrizio, García Isabel, Penadés Soledad: Glyconanoparticles as multifunctional and multimodal carbohydrate systems. Chem. Soc. Rev. 2013, 42, 4728. <http://dx.doi.org/10.1039/c2cs35420a>
  • Stefaniu Cristina, Vilotijevic Ivan, Santer Mark, Varón Silva Daniel, Brezesinski Gerald, Seeberger Peter H.: Subgelphasenstruktur in Monoschichten von Glycosylphosphatidylinositol-Glycolipiden. Angew. Chem. 2012, 124, 13046. <http://dx.doi.org/10.1002/ange.201205825>
  • Stefaniu Cristina, Vilotijevic Ivan, Santer Mark, Varón Silva Daniel, Brezesinski Gerald, Seeberger Peter H.: Subgel Phase Structure in Monolayers of Glycosylphosphatidylinositol Glycolipids. Angew. Chem. Int. Ed. 2012, 51, 12874. <http://dx.doi.org/10.1002/anie.201205825>
  • Zhao Jingsha, Liu Yuanfang, Park Hyun-Joo, Boggs Joan M., Basu Amit: Carbohydrate-Coated Fluorescent Silica Nanoparticles as Probes for the Galactose/3-Sulfogalactose Carbohydrate–Carbohydrate Interaction Using Model Systems and Cellular Binding Studies. Bioconjugate Chem. 2012, 23, 1166. <http://dx.doi.org/10.1021/bc2006169>
  • Zhang Yanyan, Dong Dengxiang, Qu Huanhuan, Sollogoub Matthieu, Zhang Yongmin: Regio- and Stereocontrolled Synthesis of 2d-Deoxy Lewisx Pentasaccharide. Eur J Org 2011, 2011, 7133. <http://dx.doi.org/10.1002/ejoc.201101062>
  • Zucca Rinaldo, Boero Mauro, Massobrio Carlo, Molteni Carla, Cleri Fabrizio: Interacting Lewis-X Carbohydrates in Condensed Phase: A First-Principles Molecular Dynamics Study. Chem B 2011, 115, 12599. <http://dx.doi.org/10.1021/jp2055816>
  • Kutkowska J., Turska-Szewczuk A., Janczarek M., Paduch R., Kaminska T., Urbanik-Sypniewska T.: Biological activity of (Lipo)polysaccharides of the exopolysaccharide-deficient mutant Rt120 derived from Rhizobium leguminosarum bv. trifolii strain TA1. Biochemistry Biokhimii?a 2011, 76, 840. <http://dx.doi.org/10.1134/S0006297911070157>
  • Kopitzki Sebastian, Jensen Knud J., Thiem Joachim: Synthesis of Benzaldehyde-Functionalized Glycans: A Novel Approach Towards Glyco-SAMs as a Tool for Surface Plasmon Resonance Studies. Chem Eur J 2010, 16, 7017. <http://dx.doi.org/10.1002/chem.200902693>
  • HAKOMORI S.: ChemInform Abstract: Carbohydrate-Carbohydrate Interaction as an Initial Step in Cell Recognition. ChemInform 2010, 22, no. <http://dx.doi.org/10.1002/chin.199139326>
  • Dong DengXiang, Gourmala Chafika, Zhang YanYan, Zhang YongMin: Synthesis of 3″- and 4″-deoxy-Lewisx trisaccharides: A useful tool for study of carbohydrate-carbohydrate interaction. Sci China Chem 2010, 53, 1963. <http://dx.doi.org/10.1007/s11426-010-4060-6>
  • Boggs Joan M., Gao Wen, Zhao Jingsha, Park Hyun-Joo, Liu Yuanfang, Basu Amit: Participation of galactosylceramide and sulfatide in glycosynapses between oligodendrocyte or myelin membranes. FEBS Letters 2010, 584, 1771. <http://dx.doi.org/10.1016/j.febslet.2009.11.074>
  • Zhang Yanyan, Dong Dengxiang, Zhou Tao, Zhang Yongmin: Study of carbohydrate–carbohydrate interactions: total synthesis of 6d-deoxy Lewisx pentaosyl glycosphingolipid. Tetrahedron 2010, 66, 7373. <http://dx.doi.org/10.1016/j.tet.2010.07.025>
  • García Isabel, Marradi Marco, Penadés Soledad: Glyconanoparticles: multifunctional nanomaterials for biomedical applications. Nanomedicine 2010, 5, 777. <http://dx.doi.org/10.2217/nnm.10.48>
  • Abe Koji, Minamikawa Hiroyuki: Mixed monolayer of dipalmitoylphosphatidylcholine and stage-specific embryonic antigen-1 (SSEA-1). Colloid Surf A Phys Eng Aspects 2009, 332, 139. <http://dx.doi.org/10.1016/j.colsurfa.2008.09.006>
  • Fernandez-Busquets X., Kornig A., Bucior I., Burger M. M., Anselmetti D.: Self-Recognition and Ca2+-Dependent Carbohydrate-Carbohydrate Cell Adhesion Provide Clues to the Cambrian Explosion. Mol Biol E 2009, 26, 2551. <http://dx.doi.org/10.1093/molbev/msp170>
  • Chen Chien-Tien, Munot Yogesh S., Salunke Santosh B., Wang Yi-Ching, Lin Ruo-Kai, Lin Chun-Cheng, Chen Chia-Chun, Liu Y-Hasin: A Triantennary Dendritic Galactoside-Capped Nanohybrid with a ZnS/CdSe Nanoparticle Core as a Hydrophilic, Fluorescent, Multivalent Probe for Metastatic Lung Cancer Cells. Adv Funct Mater 2008, 18, 527. <http://dx.doi.org/10.1002/adfm.200700449>
  • ZHU Zhen-Yuan, ZHANG Yong-Min, SUN Chao, YAO Yan-Ping: Synthesis of Protected N-Acetylchitooligosaccharide and Its Analogues: A Versatile Approach for the Synthesis of Complex Oligosaccharides of 2-Amino-2-deoxy Sugar. Chin J Chem 2008, 26, 1519. <http://dx.doi.org/10.1002/cjoc.200890275>
  • Boggs Joan M., Gao Wen, Hirahara Yukie: Signal transduction pathways involved in interaction of galactosylceramide/sulfatide-containing liposomes with cultured oligodendrocytes and requirement for myelin basic protein and glycosphingolipids. J Neurosci Res 2008, 86, 1448. <http://dx.doi.org/10.1002/jnr.21603>
  • Luo Yun, Gourmala Chafika, Dong Dengxiang, Barbault Florent, Fan Botao, Hu Yongzhou, Zhang Yongmin: First synthesis of two deoxy Lewisx pentaosyl glycosphingolipids. Glycoconjugate J 2008, 25, 335. <http://dx.doi.org/10.1007/s10719-007-9077-5>
  • Boggs Joan M., Gao Wen, Hirahara Yukie: Myelin glycosphingolipids, galactosylceramide and sulfatide, participate in carbohydrate–carbohydrate interactions between apposed membranes and may form glycosynapses between oligodendrocyte and/or myelin membranes. General Subjects 2008, 1780, 445. <http://dx.doi.org/10.1016/j.bbagen.2007.10.015>
  • Zhang Y.: Étude des interactions entre oligosaccharides impliqués dans l’adhésion cellulaire. Exemple du trisaccharide Lewisx. Annales Pharmaceutiques Françaises 2008, 66, 319. <http://dx.doi.org/10.1016/j.pharma.2008.10.001>
  • Todeschini A. R., Dos Santos J. N., Handa K., Hakomori S.-i.: Ganglioside GM2/GM3 complex affixed on silica nanospheres strongly inhibits cell motility through CD82/cMet-mediated pathway. Proceedings of the National Academy of Sciences 2008, 105, 1925. <http://dx.doi.org/10.1073/pnas.0709619104>
  • Dasgupta Somsankar, Bhat Narayan R., Spicer Samuel S., Hogan Edward L., Furuya Shigeki, Hirabayashi Yoshio: Cell-specific expression of neutral glycosphingolipids in vertebrate brain: Immunochemical localization of 3-O-acetyl-sphingosine-series glycolipid(s) in myelin and oligodendrocytes. J Neurosci Res 2007, 85, 2856. <http://dx.doi.org/10.1002/jnr.21419>
  • Gourmala Chafika, Luo Yun, Barbault Florent, Zhang Yongmin, Ghalem Sa��d, Maurel Fran��ois, Fan BoTao: Elucidation of the LewisX���LewisX carbohydrate interaction with molecular dynamics simulations: A glycosynapse model. Journal of Molecular Structure: THEOCHEM 2007, 821, 22. <http://dx.doi.org/10.1016/j.theochem.2007.06.027>
  • Lee Dong Hoon, Kim Hae-Jo, Hong Jong-In: Carbohydrate Recognition by C 3-Symmetric Polypyridine Hosts. Supramol Chem 2007, 19, 251. <http://dx.doi.org/10.1080/10610270701268799>
  • Khashimova Z. S.: Effect of deglycosylated extensin-like protein on cell culture. Chem Nat Compd 2006, 42, 364. <http://dx.doi.org/10.1007/s10600-006-0125-3>
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  • Yurkova Irina, Kisel Mikhail, Arnhold Juergen, Shadyro Oleg: Free-radical fragmentation of galactocerebrosides: a MALDI-TOF mass spectrometry study. J Chem Phys Lipids 2005, 134, 41. <http://dx.doi.org/10.1016/j.chemphyslip.2004.11.002>
  • de la Fuente Jesús M., Penadés Soledad: Glyco-quantum dots: a new luminescent system with multivalent carbohydrate display. Tet Asymm 2005, 16, 387. <http://dx.doi.org/10.1016/j.tetasy.2004.12.002>
  • Gourmala Chafika, Zhu Zhenyuan, Luo Yun, Fan Bo Tao, Ghalem Saı¨d, Hu Yongzhou, Zhang Yongmin: First synthesis of 3′-deoxy Lewisx pentasaccharide. Tet Asymm 2005, 16, 3024. <http://dx.doi.org/10.1016/j.tetasy.2005.08.007>
  • Rojo Javier, Díaz Vicente, de la Fuente Jesús M., Segura Inmaculada, Barrientos Africa G., Riese Hans H., Bernad Antonio, Penadés Soledad: Gold Glyconanoparticles as New Tools in Antiadhesive Therapy. Chem Eur J of Chem Bio 2004, 5, 291. <http://dx.doi.org/10.1002/cbic.200300726>
  • Boggs Joan M., Wang Huimin: Co-clustering of galactosylceramide and membrane proteins in oligodendrocyte membranes on interaction with polyvalent carbohydrate and prevention by an intact cytoskeleton. J Neurosci Res 2004, 76, 342. <http://dx.doi.org/10.1002/jnr.20080>
  • Hakomori Senitiroh: Carbohydrate-to-carbohydrate interaction in basic cell biology: a brief overview. Archives of Biochemistry and Biophysics 2004, 426, 173. <http://dx.doi.org/10.1016/j.abb.2004.02.032>
  • Sando Shinsuke, Narita Atsushi, Aoyama Yasuhiro: A facile route to dynamic glycopeptide libraries based on disulfide-linked sugar–peptide coupling. Biorg Med Chem Lett 2004, 14, 2835. <http://dx.doi.org/10.1016/j.bmcl.2004.03.050>
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  • YOKOYAMA Shoko, OHTA Yumiko, TAKEDA Tadahiro, IMURA Tomohiro, SAKAI Hideki, ABE Masahiko: Effect of Matrix on Surface Pressure-Responsive Morphological Change of Ganglioside GM1 (GM1), Related to the Individual Role of GM1 in Each Organ?. J Oleo Sci 2004, 53, 97. <http://dx.doi.org/10.5650/jos.53.97>
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  • Sando Shinsuke, Matsui Kazuki, Niinomi Yusuke, Sato Nobuhiko, Aoyama Yasuhiro: Facile preparation of DNA-tagged carbohydrates. Biorg Med Chem Lett 2003, 13, 2633. <http://dx.doi.org/10.1016/S0960-894X(03)00559-6>
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  • Hakomori Senitiroh: Structure, organization, and function of glycosphingolipids in membrane : . Curr Opin Hematol 2003, 10, 16. <http://dx.doi.org/10.1097/00062752-200301000-00004>
  • Hernáiz María J., de la Fuente Jesús M., Barrientos África G., Penadés Soledad: A Model System Mimicking Glycosphingolipid Clusters to Quantify Carbohydrate Self-Interactions by Surface Plasmon Resonance. Angew. Chem. 2002, 114, 1624. <http://dx.doi.org/10.1002/1521-3757(20020503)114:9<1624::AID-ANGE1624>3.0.CO;2-O>
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  • Hakomori Senitiroh, Handa Kazuko: Glycosphingolipid-dependent cross-talk between glycosynapses interfacing tumor cells with their host cells: essential basis to define tumor malignancy. FEBS Letters 2002, 531, 88. <http://dx.doi.org/10.1016/S0014-5793(02)03479-8>
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