Direct Amidation of Aldoses and Decarboxylative Amidation of α-Keto Acids: An Efficient Conjugation Method for Unprotected Carbohydrate Molecules
作者:Chia-Ching Cho、Jia-Nan Liu、Chung-Hsun Chien、Jiun-Jie Shie、Ying-Chu Chen、Jim-Min Fang
DOI:10.1021/jo802338k
日期:2009.2.20
With use of iodine as an appropriate oxidant, unprotected and unmodified aldoses undergo oxidative amidation with a variety of functionalized amines, α-amino esters, and peptides, whereas KDO, sialic acid, and other α-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
通过使用碘作为适当的氧化剂,未保护和未修饰的醛糖会与各种功能化的胺,α-氨基酯和肽进行氧化酰胺化,而KDO,唾液酸和其他α-酮酸会继续进行氧化脱羧反应原位酰胺化。在这种温和的反应条件下,糖苷键和许多其他官能团是惰性的。用于糖分子的直接连接的该反应方案在糖缀合物的一般和有效合成的发展中看起来是有希望的。