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• W2161586598 abstract "This paper presents the first ab initio conformational study of the Gal-β-1,4-[Fuc-α-1,3]-GlcNAc-β-OCH3 and Gal-β-1,4-[Fuc-α-1,3]-GlcNAc-β-OH trisaccharides (Lewis x) in the gas phase. Their lowest-energy conformers were selected first by the MM2*-SUMM conformational search technique. MM2* relative energies do not follow the same order for the two similar compounds. The molecular geometries and energies of the lowest-energy rotamers (7 of the acetal and 11 of the hemiacetal) were further analyzed at the HF/6-31G(d) level of theory. The ab initio method yields the same energetic order for the rotamers of the two molecules with considerably larger energetic differences for the first 7 rotamers: the MM2* method provides 0.3−0.5 kcal/mol, whereas the HF/6-31G(d) method provides 4.5 kcal/mol. In the most stable MM2* structures the hydrogen-bonded chains of galactose (in counterclockwise direction) and fucose (in clockwise direction) are not connected. The Gal(O6H) is a hydrogen bond donor (in clockwise direction) to the O3 glycosidic oxygen of GlcNAc. The Fuc(O2H)→(OC)GlcNAc interaction connects the fucose and GlcNAc. In contrast, the most stable HF/6-31G(d) structure has a long chain of seven ordered hydrogen bonds including a Gal(O6H)→(O3)Fuc interaction (with clockwise hydrogen-bonded chain in galactose and fucose). The torsion angles for Fuc-α-1,3-GlcNAc and Gal-β-1,4-GlcNAc glycosidic bonds agree well in the solid, liquid, and gas phases. For example there is a rather good overlap between the GlcNAc moiety of one of the X-ray structures and the most similar HF/6-31G(d) structure. The stacking of the fucose and galactose moieties is similar. The orientations of the hydroxyl groups are usually different, as they are influenced by intramolecular hydrogen bonding in the gas-phase Hartree−Fock structure versus intermolecular hydrogen bonding in the solid-phase X-ray structure." @default.
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• W2161586598 date "2000-03-22" @default.
• W2161586598 modified "2023-09-24" @default.
• W2161586598 title "Ab Initio Study of Lowest-Energy Conformers of Lewis X (Le^x) Trisaccharide" @default.
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• W2161586598 doi "https://doi.org/10.1021/jp9935034" @default.
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