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Theoretical studies on the conformation of saccharides. XIV. Structure and conformational properties of the glycosylamines

✍ Scribed by Tibor Kožár; Igor Tvaroška

Publisher
Wiley (John Wiley & Sons)
Year
1990
Tongue
English
Weight
586 KB
Volume
29
Category
Article
ISSN
0006-3525

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✦ Synopsis

The 2-methylaminotetrahydropyran was used as a model to study conformational properties of the N-glycosidic linkage in glycosylamines. Relaxed two-dimensional conformational (%, 9 ) maps in 20 solvents were calculated by a method in which the total energy is divided into the energy of the isolated molecule and the solvation energy. Molecular geometry optimization has been carried out for each conformer using the quantum chemical method PCILO. The calculated variations of the geometry are consistent with the results obtained by the statistical analysis of available experimental data retrieved from the Cambridge Structural Database. The calculated abundances of conformers show that the polarity of the solvent has little effect on the anomeric ratio, and the form having the methylamino group equatorial is favored in all considered solvents.

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