RT info:eu-repo/semantics/article T1 The shape of D-glucosamine A1 Peña Calvo, María Isabel A1 Kolesnikova, Lucie A1 Cabezas, Carlos A1 Bermúdez Arias, María Celina A1 Berdakin, Matías A1 Simão, Alcides A1 Alonso Hernández, José Luis AB The bioactive amino monosaccharide D-glucosamine has been generated in gas phase via laser ablation ofD-glucosamine hydrochloride. Three cyclic α-4C1 pyranose forms have been identified using Fouriertransform microwave techniques. Stereoelectronic hyperconjugative forces – essentially linked with theanomeric or gauche effect – and cooperative OH…O, OH…N and NH…O chains, extended along the entiremolecule, are found to be the main factors driving the conformational behavior. The orientation of theNH2 group within each conformer has been determined by the values of the nuclear quadrupole constants.The results have been compared with those recently obtained for the archetypical D-glucose. YR 2014 FD 2014 LK http://uvadoc.uva.es/handle/10324/22655 UL http://uvadoc.uva.es/handle/10324/22655 LA eng NO Physical Chemistry Chemical Physics, 2014,16, 23244-23250 DS UVaDOC RD 25-nov-2024