Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A Conformational Study of Linkage Positions in Oligosaccharides Investigated by 2-D NMR Spectroscopy and Molecular Modeling

  • Published : 2003.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

The conformation of synthetic oligosaccharide can be elucidated by employing molecular modeling and highfield proton NMR (nuclear magnetic resonance) spectroscopy. Information with respect to the composition and configuration of saccharide residues and the sequence and linkage positions of the oligosaccharide can be obtained by employing a variety of one- and two-dimensional NMR techniques and molecular modeling. These techniques are also useful in establishing the solution conformation of the oligosaccharide moiety. This study is focused on the elucidation of linkage positions of synthetic trisaccharides, Gal(β1-4)Glc(β1-3)Glc, Gal(β1-4)Glc(β1-4)Glc and Gal(β1-4)Glc(β1-6)Glc.

Keywords

References

  1. Rao, V. S. R.; Qasba, P. K.; Balaji, P. V.; Chandrasekaran, R. Conformation of Carbohydrates; Harwood Academic Publishers: Amsterdam, Netherlands, 1998; pp 29-42, pp 131-182.
  2. Kobata, A. Acc. Chem. Res. 1993, 26, 319. https://doi.org/10.1021/ar00030a004
  3. French, A. D.; Mouhous-Riou, N.; Perez, S. Carbohyd. Res. 1993, 247, 51. https://doi.org/10.1016/0008-6215(93)84240-7
  4. Krishna, N. R.; Choe, B.; Prabhakaran, M.; Ekborg, G. C.; Roden, L.; Harvey, S. C. J. Biol. Chem. 1990, 265, 18256.
  5. Lee, K.; Kim, Y. Bull. Korean Chem. Soc. 1996, 17, 118. https://doi.org/10.1007/BF02789264
  6. Shim, G.; Lee, S.; Kim, Y. Bull. Korean Chem. Soc. 1997, 18, 415.
  7. Yoon, E. Y.; Laine, R. A. Glycobiology 1992, 2, 161. https://doi.org/10.1093/glycob/2.2.161
  8. Bax, A.; Eagan, W.; Kovac, P. J. Carbohyd. Chem. 1984, 3, 593. https://doi.org/10.1080/07328308408057920
  9. Kumar, A.; Ernst, R. R.; Wuthrich, K. Biochim. Biophys. Acta 1980, 95, 1.
  10. IUPAC Tentative Rules for the Nomenclature of Organic Chemistry, Eur. J. Biochem. 1971, 18, 151. https://doi.org/10.1111/j.1432-1033.1971.tb01226.x
  11. Gamlan, A.; Ramanowska, E.; Dabrowski, U.; Dabrowski, J. Biochemistry 1991, 30, 5032. https://doi.org/10.1021/bi00234a027
  12. Egge, H.; Dabrowski, J.; Hanfland, P. Pure Appl. Chem. 1984, 56, 807. https://doi.org/10.1351/pac198456070807
  13. Kannagi, R.; Fukushi, Y.; Tachikawa, T.; Noda, A.; Shin, S.; Shigeta, K.; Hiraiwa, K.; Fukuda, N.; Inamoto, T.; Hakomori, S.; Imura, H. Cancer Res. 1986, 46, 2619.
  14. Lowe, J. B.; Stoolman, L. M.; Nair, R. P.; Larsen, R. D.; Berhend, T. L.; Marks, R. M. Cell 1990, 63, 475. https://doi.org/10.1016/0092-8674(90)90444-J
  15. Li, J. H.; Allinger, N. L. MM2 Program (QCPE 543); University of Georgia: 1987.
  16. Duben, A. J.; Hricovini, M.; Tvaroska, I. Carbohyd. Res. 1993, 247, 71. https://doi.org/10.1016/0008-6215(93)84242-X

Cited by

  1. Conformational Search on the Lewis X Structure by Molecular Dynamic: Study of Tri- and Pentasaccharide vol.2012, pp.1687-935X, 2012, https://doi.org/10.1155/2012/725271
  2. Development of Fast Synthetic Method and Analytical Technology for Linkage-Isomeric Oligosaccharides vol.277-279, pp.1662-9795, 2005, https://doi.org/10.4028/www.scientific.net/KEM.277-279.33
  3. Applications of Tandem Mass Spectrometry in the Structure Determination of Permethylated Sialic Acid-containing Oligosaccharides vol.26, pp.9, 2003, https://doi.org/10.5012/bkcs.2005.26.9.1347
  4. Molecular Simulations and Conformational Studies of Fucoseα1-3)Gal(β1-X)GlcNAc where X=3, 4, or 6 Oligosaccharides vol.29, pp.9, 2003, https://doi.org/10.5012/bkcs.2008.29.9.1755
  5. A Systematic NMR Determination of α-D-Glucooligosaccharides, Effect of Linkage Type, Anomeric Configuration and Combination of Different Linkages Type on 13C Chemical Shifts for the D vol.30, pp.11, 2003, https://doi.org/10.5012/bkcs.2009.30.11.2535