Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages
Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages
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DOI：
10.1038/nprot.2008.153
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发表时间：
2008-01-01
期刊：
影响因子：
14.8
通讯作者：
Danishefsky, Samuel J.
中科院分区：
文献类型：
--
作者：
Li, Xuechen;Danishefsky, Samuel J.
本方案描述了在羧酸和异硝基之间反应的基础上制备n -甲基天冬酰胺连接的糖基氨基酸。在微波/热裂解条件下，羧酸可以与异腈偶联，无需外部催化剂即可生成n -甲酰基酰胺，并可进一步发展为相应的酰胺：n -甲基酰胺和n -甲基酰酰胺。-半乳糖酰基异腈(7)与受保护的天冬氨酸在微波条件下30分钟立体选择性反应得到-半乳糖酰基- n -甲酰基-天冬酰胺(9)。进一步的化学转化很容易将9转化为β -半乳糖酰基- n -甲基-天冬酰胺（11）。
This protocol describes the preparation of an N-methyl-asparagine-linked glycosyl amino acid, on the basis of a reaction between carboxylic acids and isonitriles. Under microwave/thermolysis, carboxylic acids can couple with isonitriles without an external catalyst to form N-formyl-amides, which may be further advanced to the corresponding amides, N-methyl amide and N-methyloyl amide. The example reaction of beta-galactopyranosyl isonitrile (7) with a protected aspartic acid under microwave condition in 30 min stereoselectively leads to a beta-galactopyranosyl-N-formyl-asparagine (9). Further chemical transformations readily convert 9 into beta-galactopyranosyl-N-methyl-asparagine (11).