Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Molecular Simulations and Conformational Studies of Fucoseα1-3)Gal(β1-X)GlcNAc where X=3, 4, or 6 Oligosaccharides

  • Yoo, Eun-Sun (Dept. of Oriental Medicine Industry, Honam University) ;
  • Yoon, In-Mo (Dept. of Game Animation, Honam University)
  • Published : 2008.09.30
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Abstract

Energy minimization and conformational studies of molecular ions generated by ESI (electrospray ionization) tandem mass spectrometry (MS/MS) can be used for the discrimination of stereoisomeric permethylated and sodium cationized trisaccharides. Sets of fucose-containing trisaccharides having different internal and terminal linkages have been synthesized to analyze the reducing terminal linkage positions using BT and IT fusion approaches. A detailed investigation has been undertaken on the conformational behaviors of four trisaccharide fragments from human milk and blood group determinants of Type 1 and Type 2, namely Fuc($\alpha$1- 3)Gal($\beta$1-3)GalNAc and Fuc($\alpha$1-3)Gal($\beta$1-X)GlcNAc where X = 3, 4 and 6 using molecular modeling methods. Three dimensional rigid and adiabatic phi-psi-energy maps (Surfer program) describing the energy as a function of rotation around corresponding glycosidic linkages were calculated by SYBYL molecular modeling and MM4 force field programs conjunction with cleavage energies of ESI MS/MS for the side group orientations. This approach predicted conformational behaviors exhibited by isomer saccharides for future applications on biologically active glycoconjugates and to exploit a faster method of synthesizing a series of structural isomeric oligosaccharides.

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References

  1. Schachter, H. PNAS 2005, 102, 15721 https://doi.org/10.1073/pnas.0507659102
  2. Werz, D. B.; Castagner, B.; Seeberger, P. H. JACS 2007, 129, 2770 https://doi.org/10.1021/ja069218x
  3. Seeberger, P. H.; Werz, D. B. Nature 2007, 446, 1046 https://doi.org/10.1038/nature05819
  4. Scanlan, C. N.; Offer, J.; Zitzmann, N.; Dwek, R. A. Nature 2007, 446, 1038 https://doi.org/10.1038/nature05818
  5. Bosques, C. J.; Tschampel, S. M.; Woods, R. J.; Imperiali, B. JACS 2004, 126, 8421 https://doi.org/10.1021/ja0496266
  6. Chol, H.; Choe, E.; Yang, E.; Jang, S.; Park, C. Bull. Korean Chem. Soc. 2007, 28, 2354 https://doi.org/10.5012/bkcs.2007.28.12.2354
  7. Yu, S.; Wu, S.; Khoo, K. Glycoconj. J. 2006, 23, 355 https://doi.org/10.1007/s10719-006-8492-3
  8. Kang, D.; Jung, K.; Kim, S.; Lee, S.; Jhon, G.; Kim, Y. Bull. Korean Chem. Soc. 2007, 28, 2209 https://doi.org/10.5012/bkcs.2007.28.12.2209
  9. Kelienberger, E.; Rodrigo, J.; Muller, P.; Rognan, D. Proteins 2004, 57, 225 https://doi.org/10.1002/prot.20149
  10. French, A. D.; Johnson, G. P. Cellulose 2004, 11, 5 https://doi.org/10.1023/B:CELL.0000014765.94239.fe
  11. Rao, V. S. R.; Qasba, P. K.; Balaji, P. V.; Chandrasekaran, R. Conformation of Carbohydrates; Harwood Academic Publishers: 1998; pp 49-190
  12. Boons, G.; Demchenko, A. V. Chem. Rev. 2000, 100, 4539 https://doi.org/10.1021/cr990313g
  13. Yoo, E.; Yoon, I. Key Engineering Materials 2005, 277, 33 https://doi.org/10.4028/www.scientific.net/KEM.277-279.33
  14. Yoo, E.; Laine, R. A. Biol. Mass Spectrom. 1992, 21, 479 https://doi.org/10.1002/bms.1200211003
  15. Yoo, E. Bull. Korean Chem. Soc. 2003, 24, 339 https://doi.org/10.5012/bkcs.2003.24.3.339
  16. Yoo, E. Bull. Korean Chem. Soc. 2001, 22, 293
  17. Yoo, E. Bull. Korean Chem. Soc. 2005, 26, 339
  18. Duus, J.; Gotfredsen, C. H.; Bock, K. Chem. Rev. 2000, 100, 4589 https://doi.org/10.1021/cr990302n
  19. Lee, K.; Kim, Y. Bull. Korean Chem. Soc. 1996, 17, 18
  20. Ciucanu, I.; Kerek, F. Carbohydr. Res. 1984, 131, 209 https://doi.org/10.1016/0008-6215(84)85242-8
  21. Gunnarsson, A. Glycoconjugate J. 1987, 4, 239 https://doi.org/10.1007/BF01048429
  22. IUPAC Tenetative Rules for the Nomenclature of Organic Chemistry Eur. J. Biochem. 1971, 18, 151 https://doi.org/10.1111/j.1432-1033.1971.tb01226.x
  23. Domon, B.; Costello, C. E. Glycoconjugate J. 1988, 5, 397 https://doi.org/10.1007/BF01049915
  24. Egge, H.; Peter-Katalinic, J. Mass Spectrometry Review 1987, 6, 331 https://doi.org/10.1002/mas.1280060302
  25. French, A. D.; Tran, V. H.; Perez, S. Computer Modeling Carbohydrate Molecules; American Chemical Society: Washington D. C., 1989; pp 191-212
  26. French, A. D. Carbohydr. Res. 1989, 188, 206 https://doi.org/10.1016/0008-6215(89)84072-8

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