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Issue 42, 2014

The shape of d-glucosamine

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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.

Graphical abstract: The shape of d-glucosamine

Supplementary files

Article information


Submitted
12 Aug 2014
Accepted
16 Sep 2014
First published
16 Sep 2014

Phys. Chem. Chem. Phys., 2014,16, 23244-23250
Article type
Paper

The shape of D-glucosamine

I. Peña, L. Kolesniková, C. Cabezas, C. Bermúdez, M. Berdakin, A. Simão and J. L. Alonso, Phys. Chem. Chem. Phys., 2014, 16, 23244 DOI: 10.1039/C4CP03593C

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