Quantum molecular modeling of hyaluronan

Molecular modeling of the secondary structure of hyaluronan is presented on the basis of the following molecular models: GlcA, GlcNAc, GlcA 1 → 3 GlcNAc, GlcNAc 1 → 4 GlcA, GlcNAc 1 → 4 GlcA 1 → 3 GlcNAc and GlcA 1 → 3 GlcNAc 1 → 4 GlcA. The optimized geometries of the monosaccharides obtained using...

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Bibliographic Details
Published in:Journal of molecular structure. Theochem 1997-05, Vol.395, p.477-508
Main Authors: Moulabbi, M., Broch, H., Robert, L., Vasilescu, D.
Format: Article
Language:English
Subjects:
Conformational analysis
Electrostatic properties
Hyaluronan
Quantum molecular modeling
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Summary:Molecular modeling of the secondary structure of hyaluronan is presented on the basis of the following molecular models: GlcA, GlcNAc, GlcA 1 → 3 GlcNAc, GlcNAc 1 → 4 GlcA, GlcNAc 1 → 4 GlcA 1 → 3 GlcNAc and GlcA 1 → 3 GlcNAc 1 → 4 GlcA. The optimized geometries of the monosaccharides obtained using AM1 and ab initio STO-3G methods are in good agreement with the crystallographic data. The flexibility of the β1 → 3 and β1 → 4 linkages was studied using AM1 and ab initio HF/3-21G methods. Our study shows that in all cases the β1 → 3 linkage is more flexible than the β1 → 4 linkage. The minimal energy conformations of the di- and trisaccharides studied correspond to a compact conformation for the β1 → 3 linkage and to standard conformations in agreement with the left-handed helices of sodium hyaluronate or calcium hyaluronate. The electrostatic properties and the frontier orbital characteristics obtained at the HF/3-21G level are discussed.
ISSN:0166-1280
1872-7999
DOI:10.1016/S0166-1280(97)00021-3