Peptide synthesis using unprotected peptides through orthogonal coupling methods
Peptide synthesis using unprotected peptides through orthogonal coupling methods
复制标题
DOI：
10.1073/pnas.92.26.12485
复制
发表时间：
1995-12-19
影响因子：
11.1
通讯作者：
Shao, J
中科院分区：
文献类型：
--
作者：
Tam, JP;Lu, YA;Shao, J
我们描述了一种方法，通过正交偶联方法从不含保护基团的片段合成肽，以捕获酰基片段作为硫酯，然后进行分子内酰基转移到胺组分，形成肽键。通过三烷基膦和烷基硫醇介导的硫醇-硫酯交换或通过C-α-硫代羧酸与β-溴代氨基酸反应的硫酯化反应，实现了两种正交偶联方法以得到共价酯中间体。利用这种方法，在水溶液中偶联范围从4至37个残基的未保护的片段，以高效地得到长达54个残基的游离肽。
We describe an approach to the synthesis of peptides from segments bearing no protecting groups through an orthogonal coupling method to capture the acyl segment as a thioester that then undergoes an intramolecular acyl transfer to the amine component with formation of a peptide bond. Two orthogonal coupling methods to give the covalent ester intermediate were achieved by either a thiol-thioester exchange mediated by a trialkylphosphine and an alkylthiol or a thioesterification by C-alpha-thiocarboxylic acid reacting with a beta-bromo amino acid. With this approach, unprotected segments ranging from 4 to 37 residues were coupled in aqueous solution to give free peptides up to 54 residues long with high efficiency.