Direct Amidation of Aldoses and Decarboxylative Amidation of α-Keto Acids: An Efficient Conjugation Method for Unprotected Carbohydrate Molecules

• DOI: 10.1021/jo802338k
• Publication Date: 2009-01-21T15:34:15Z
• Authors: Chia-Ching Cho; Jia-Nan Liu; Chung-Hsun Chien; Jiun-Jie Shie; Ying-Chu Chen; Jim-Min Fang
• Keywords: Oxidative decarboxylation; Decarboxylation; Glycoconjugate; Carbohydrate chemistry

With use of iodine as an appropriate oxidant, unprotected and unmodified aldoses undergo oxidative amidation with a variety functionalized amines, α-amino esters, peptides, whereas KDO, sialic acid, other α-keto acids proceed decarboxylation followed by in situ amidation. Glycoside bond many functional groups are inert under such mild reaction conditions. This protocol for direct ligation carbohydrate molecules looks promising the development general efficient synthesis glycoconjugates.