Traverssi Miqueas G, Manzano Verónica E, Varela Oscar, Colomer Juan P
Departamento de Química Orgánica, Universidad Nacional de Córdoba, Facultad de Ciencias Químicas, Ciudad Universitaria Edificio de Ciencias II Córdoba Argentina
Instituto de Investigaciones en Fisico-Química de Córdoba (INFIQC), Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET) UNC Argentina.
RSC Adv. 2024 Jan 16;14(4):2659-2672. doi: 10.1039/d3ra07763b. eCollection 2024 Jan 10.
The synthesis of -glycosyl amides typically involves the use of glycosyl amines as direct precursors, resulting in low yields due to hydrolysis and the loss of stereocontrol through anomerization processes. In this study, a sequential synthesis of -glycosyl amides is proposed, employing glycosyl amines as intermediates obtained from glycosyl azides. Derivatives with , , or configurations were synthesized. Hexose derivatives were obtained under stereocontrol to give only the β anomer, while the derivatives provided a mixture of α and β anomers. Conformational analysis revealed that all β anomers adopted the C conformation, while α anomers were found in the C chair as the major conformer. After de--acetylation, the derivatives containing a galactose unit were evaluated as inhibitors of β-galactosidase from and were found to be moderate inhibitors.
-糖基酰胺的合成通常涉及使用糖基胺作为直接前体，由于水解以及通过异头化过程导致立体控制的丧失，产率较低。在本研究中，提出了一种-糖基酰胺的顺序合成方法，使用从糖基叠氮化物获得的糖基胺作为中间体。合成了具有、或构型的衍生物。在立体控制下获得己糖衍生物，仅得到β异头物，而衍生物提供了α和β异头物的混合物。构象分析表明，所有β异头物均采用C构象，而α异头物以C椅式作为主要构象体被发现。在脱-乙酰化后，对含有半乳糖单元的衍生物作为来自的β-半乳糖苷酶抑制剂进行了评估，发现它们是中等强度的抑制剂。
