Peña Isabel, Kolesniková Lucie, Cabezas Carlos, Bermúdez Celina, Berdakin Matías, Simão Alcides, Alonso José L
Grupo de Espectroscopía Molecular (GEM), Unidad Asociada CSIC, Edificio Quifima, Laboratorios de Espectroscopia y Bioespectroscopia, Parque Científico UVa, Universidad de Valladolid, 47011 Valladolid, Spain.
Phys Chem Chem Phys. 2014 Nov 14;16(42):23244-50. doi: 10.1039/c4cp03593c.
The bioactive amino monosaccharide D-glucosamine has been generated in the gas phase via laser ablation of D-glucosamine hydrochloride. Three cyclic α-(4)C1 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.
生物活性氨基单糖D-葡萄糖胺已通过激光烧蚀盐酸D-葡萄糖胺在气相中生成。利用傅里叶变换微波技术鉴定出了三种环状α-(4)C1吡喃糖形式。发现立体电子超共轭力——本质上与异头效应或邻位交叉效应相关——以及沿整个分子延伸的协同OH···O、OH···N和NH···O链是驱动构象行为的主要因素。每个构象异构体中NH2基团的取向已由核四极耦合常数的值确定。已将结果与最近针对典型D-葡萄糖获得的结果进行了比较。
