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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 9
BKCSDE 29(9)
September 20, 2008 

Molecular Simulations and Conformational Studies of
Fucose(α1-3)Gal(β1-X)GlcNAc where X=3, 4, or 6 Oligosaccharides
Eunsun Yoo*, Inmo Yoon
Molecular modeling, Fucose, ESI tandem mass spectrometry
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(α1- 3)Gal(β1-3)GalNAc and Fuc(α1-3)Gal(β1-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.
1755 - 1760
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