Jump to main content
Jump to site search

Issue 42, 2014
Previous Article Next Article

The shape of d-glucosamine

Author affiliations


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

Back to tab navigation

Supplementary files

Article information

12 Aug 2014
16 Sep 2014
First published
16 Sep 2014

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

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

Social activity

Search articles by author