Cho Chia-Ching, Liu Jia-Nan, Chien Chung-Hsun, Shie Jiun-Jie, Chen Ying-Chu, Fang Jim-Min
Department of Chemistry, National Taiwan University, Taipei 106, Taiwan.
J Org Chem. 2009 Feb 20;74(4):1549-56. doi: 10.1021/jo802338k.
With use of iodine as an appropriate oxidant, unprotected and unmodified aldoses undergo oxidative amidation with a variety of functionalized amines, alpha-amino esters, and peptides, whereas KDO, sialic acid, and other alpha-keto acids proceed with oxidative decarboxylation followed by in situ amidation. Glycoside bond and many other functional groups are inert under such mild reaction conditions. This reaction protocol for direct ligation of carbohydrate molecules looks promising in the development of a general and efficient synthesis of glycoconjugates.
使用碘作为合适的氧化剂时，未保护和未修饰的醛糖会与多种官能化胺、α-氨基酯和肽发生氧化酰胺化反应，而KDO、唾液酸和其他α-酮酸则先进行氧化脱羧，然后进行原位酰胺化。糖苷键和许多其他官能团在这种温和的反应条件下是惰性的。这种用于碳水化合物分子直接连接的反应方案在开发通用且高效的糖缀合物合成方法方面看起来很有前景。
