Highly efficient and fast pre-activation cyclization of the long peptide: Succinimidyl ester-amine reaction revisited

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• 作者：Se-Hwan Choi ; Woo-jin Jeong ; Sung-ju Choi ; Yong-beom Lim ; ^{yblim@yonsei.ac.kr" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Macrocyclic peptides ; Cyclization ; Pre-activation ; Succinimidyl ester ; End-capping
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2015
• 出版时间：15 November 2015
• 年：2015
• 卷：25
• 期：22
• 页码：5335-5338
• 全文大小：660 K

文摘

A new method for the pre-activation cyclization of a long peptide is described. The approach involves the formation of a pre-activated succinimidyl ester species in advance of amidation, which completely eliminates the potentially troublesome amine end-capping side reaction. The cyclization reactions proceed with high efficiency and fast reaction kinetics for the long peptide with 25 residues. The exploration and large-scale preparation of synthetic cyclic peptides should become more accessible and feasible with this approach. This method has a potential to be further applied for the synthesis of much longer and more complex cyclic peptides.