THE CONFORMATIONAL BEHAVIOUR OF GLUCOSAMINE

I. PEÑA; L. KOLESNIKOVA; C. CABEZAS; C. BERMUDEZ; M. BERDAKIN; A. SIMAO; J. L. ALONSO

Congreso; 69th International Symposium on Molecular Spectroscopy; 2014

A laser ablation method has been successfully used to vaporize the bioactive amino monosaccharide D-glucosamine. Three cyclic -4C1 pyranose forms have been identified using a combination of CP-FTMW and LA-MB-FTMW spec- troscopy. Stereoelectronic hyperconjugative factors, like those associated with anomeric or gauche effects, as well as the cooperative OH O, OH N and NH O chains, extended along the entire molecule, are the main factors driving the conformational behavior. All observed conformers exhibit a counter-clockwise arrangement (cc) of the network of intramolecular hydrogen bonds. The results are compared with those recently obtained for D-glucose.a