CHEMICAL LIGATION APPROACH TO FORM A PEPTIDE-BOND BETWEEN UNPROTECTED PEPTIDE SEGMENTS - CONCEPT AND MODEL STUDY
CHEMICAL LIGATION APPROACH TO FORM A PEPTIDE-BOND BETWEEN UNPROTECTED PEPTIDE SEGMENTS - CONCEPT AND MODEL STUDY
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DOI：
10.1021/ja00089a001
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发表时间：
1994-05-18
影响因子：
15
通讯作者：
TAM, JP
中科院分区：
文献类型：
--
作者：
LIU, CF;TAM, JP
我们描述了一种化学连接肽片段的新方法，无需保护基团且无需激活 C-α-羧基。该方法的关键反应是基于分子内O,N-酰基转移反应来实现高有效摩尔浓度，从而使两个紧密相邻的官能团能够高效、选择性地彼此反应。该方法的特异性归因于带有酯乙醇醛的羧基组分和带有1,2-氨基硫醇基团（例如N-末端半胱氨酸残基）的氨基组分之间容易形成环。通过小化合物的模型研究和十五肽的合成验证了该方案的可行性。
We describe a novel approach to the chemical ligation of peptide segments with no protecting groups and no activation of the C-alpha-carboxyl group. The key reaction of this approach is based on the intramolecular O,N-acyl transfer reaction to achieve high effective molarity so that two closely neighbored functional groups can react efficiently and selectively with each other. The specificity of this approach is contributed by the facile ring formation between the carboxyl component bearing an ester glycolaldehyde and the amino component bearing a 1,2-amino thiol group such as a N-terminal cysteine residue. The feasibility of this scheme was verified by model studies on small compounds and the synthesis of a pentadecapeptide.