Synthetic Cellular Chemistry Laboratory

Glycoconjugates such as glycoproteins and glycolipids contain glycan chains. The latter are intimately connected with in various biological events, such as cell-cell recognition, differentiation and malignant transformation. It is becoming clear that they also play critical roles in glycoprotein activity control, stabilization, folding and degradation. Synthesis of complex and structurally diverse glycan chains is a challenging subject in synthetic organic chemistry. It is attracting a broad attention as an important area at the interface with biology. Based on these backgrounds, various attempts to synthesize glycoconjugates, particularly glycoproteins and related compounds are under current investigation, which aims at the clarification of biological roles of glycan chains. The development of new methodologies in glycan chain synthesis is another major on going subject of investigation. This program aims at establishment of fully selective and rapid assembly of glycoconjugate related glycan chains. Computational approach on glycan chains is also performed in order to clarify the conformation of biologically active oligosaccharides.

Research Subjects

• Development of syntheic methodologies for creation of glycoconjugate-related molecules
• Synthetic sutdies on biologically important glycoconjugates
• Studies on intracellular functions of glycoproteins
• Development of polysaccharide derived materials

Publications

1. Ishiwata, A., Sakurai, A., Nishimiya, Y., Tsuda, S., and Ito, Y.:
   "Synthetic study and structural analysis of the antifreeze agent xylomannan from Upis ceramboides"
   J. Am. Chem. Soc., 133, 19524-19535 (2011)
   
2. Nakagawa, Y., Doi, T., Masuda, Y., Tagegoshi, K., Igarashi, Y., and Ito, Y.:
   "Mapping of the primary mannose binding site of Pradimicin A"
   J. Am. Chem. Soc., 133, 17485-17493 (2011)
   
3. Ishiwata, A. and Ito, Y.:
   "Synthesis of docosasaccharide arabina motif of mycobacterial cell wall"
   J. Am. Chem. Soc. 133, 2275-2291 (2011)
4. Nakagawa, Y., Masuda, Y., Yamada, K., Doi, T., Takegoshi, K., Igarashi, Y., and Ito, Y.:
   "Solid-state NMR spectroscopic analysis of the Ca2+-dependent mannose binding of pradimicin A"
   Angew. Chem. Int. Ed. 50, 6084-6088 (2011)
5. Totani, K., Ihara, Y., Tsujimoto, T., Matsuo, I., and Ito, Y.:
   "The recognition motif of the folding-sensor enzyme UDP-Glc:glycoprotein glucosyltransferase"
   Biochemistry 48, 2933-2940 (2009)
6. Manabe, S., Ishii, K., Hashizume, D., Koshino, H., and Ito, Y.:
   "Evidence for endocyclic cleavage of conformationally restricted glycopyranosides"
   Chem. Eur. J., 6894-6901 (2009)
7. Lee, Y.J., Ishiwata, A., and Ito, Y.:
   "Stereoselective Synthesis of β-L-Rhamnopyranosides"
   J. Am. Chem. Soc., 130, 6330-6331 (2008)
   
8. Totani, K., Ihara, Y., Matsuo, I., and Ito, Y.:
   "Effects of macromolecular crowding on glycoprotein processing enzymes"
   J. Am. Chem. Soc., 130, 2101-2107 (2008)
   
9. Manabe, S., Ishii, K., and Ito, Y.:
   "N-Benzyl-2,3-oxazolidinone as a glycosyl donor for selective a-glycosylation and one-pot oligosaccharide synthesis involving 1,2-cis-glycosylation"
   J. Am. Chem. Soc., 130, 10666-10667 (2006)
   
10. Totani, K., Matsuo, I., Ihara, Y., and Ito, Y.:
    "Substrate specificity analysis of endoplasmic reticulum glucosidase II using synthetic high-mannose-type glycans"
    J. Biol. Chem., 281, 31502-31508 (2006)