Boc-SPPS: Compatible Linker for the Synthesis of Peptide o-Aminoanilides

详细信息    查看全文

• 作者：Joachim Weidmann ; Elena Dimitrijevi? ; J?rg D. Hoheisel ; Philip E. Dawson
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：January 15, 2016
• 年：2016
• 卷：18
• 期：2
• 页码：164-167
• 全文大小：331K
• ISSN：1523-7052

文摘

A protection strategy is described for the efficient synthesis of peptide o-aminoanilides using in situ neutralization protocols for Boc-SPPS. On-resin protection of Boc-protected aminoacyl o-aminoanilides is achieved with 2-chlorobenzyl chloroformate. Activation through a peptidyl-benzotriazole intermediate allows for facile conversion to peptide-thioesters for use in native chemical ligation. In addition to providing a robust alternative to established thioester resins, as a latent thioester, the peptide o-aminoanilide has broad utility in convergent ligation strategies.