The shape of d-glucosamine

Literature Information

Publication Date 2014-09-16
DOI 10.1039/C4CP03593C
Impact Factor 3.676
Authors

Isabel Peña, Lucie Kolesniková, Carlos Cabezas, Celina Bermúdez, Matías Berdakin, Alcides Simão, José L. Alonso


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Abstract

The bioactive amino monosaccharide D-glucosamine has been generated in the gas phase via laser ablation of D-glucosamine hydrochloride. Three cyclic α-4C1 pyranose forms have been identified using Fourier transform microwave techniques. Stereoelectronic hyperconjugative forces – essentially linked with the anomeric or gauche effect – and cooperative OH⋯O, OH⋯N and NH⋯O chains, extended along the entire molecule, are found to be the main factors driving the conformational behavior. The orientation of the NH2 group within each conformer has been determined by the values of the nuclear quadrupole coupling constants. The results have been compared with those recently obtained for the archetypical D-glucose.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
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