Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis,ACS Catalysis

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Zn-Catalyzed Nicotinate-Directed Transamidations in Peptide Synthesis
ACS Catalysis ( IF 11.3 ) Pub Date : 2020-03-20 , DOI: 10.1021/acscatal.9b05074
Karlijn Hollanders _{1,

2} , Evelien Renders ₂ , Charlène Gadais _{1,

2} , Dario Masullo ₂ , Laurent Van Raemdonck ₂ , Clarence C. D. Wybon ₂ , Charlotte Martin ₁ , Wouter A. Herrebout ₃ , Bert U. W. Maes ₂ , Steven Ballet ₁

Affiliation

A chemoselective and catalytic transamidation for peptide synthesis is described. Transamidation under Zn catalysis is chemoselectively achieved by amino acid amide/peptidic amide derivatization with a tert-butyl nicotinate (tBu-nic) directing group. The directing group could be easily introduced on protected amino acid amides via Pd-catalyzed amidation with tert-butyl 2-chloronicotinate (tBu-nicCl). Under standard peptide coupling/deprotection conditions, the tBu-nic-equipped amino acid amides proved to be fully inert, allowing them to be easily built-in in complex molecules. The disclosed method was evaluated in the synthesis of diverse dipeptides, in dipeptide segment coupling, in side-chain modification of a solid-supported tetra-/pentapeptide, and in the macrocyclization of a heptapeptide.

中文翻译：

锌催化的烟酸酯定向转氨作用的肽合成

描述了用于肽合成的化学选择和催化转氨基。锌催化下的氨基转移是通过烟酰胺叔丁酸酯（t Bu-nic）导向基团的氨基酸酰胺/肽酰胺衍生化而实现的。通过用2-氯烟酸叔丁酯（t Bu-nicCl）进行Pd催化的酰胺化，可以容易地将导向基团引入到受保护的氨基酸酰胺上。在标准肽偶联/去保护条件下，t带有Bunic的氨基酸酰胺被证明是完全惰性的，使它们易于内置在复杂分子中。在各种二肽的合成，二肽链段偶联，固相支持的四肽/五肽的侧链修饰以及七肽的大环化中评估了所公开的方法。

更新日期：2020-03-21

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