Department of Chemistry, Massachusetts Institute of Technology , 18-563, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.
Org Lett. 2016 Mar 18;18(6):1226-9. doi: 10.1021/acs.orglett.5b03626. Epub 2016 Mar 7.
A chemistry for the facile two-component macrocyclization of unprotected peptide isocyanates is described. Starting from peptides containing two glutamic acid γ-hydrazide residues, isocyanates can be readily accessed and cyclized with hydrazides of dicarboxylic acids. The choice of a nucleophilic linker allows for the facile modulation of biochemical properties of a macrocyclic peptide. Four cyclic NYAD-1 analogues were synthesized using the described method and displayed a range of biological activities.
本文描述了一种用于非保护肽异氰酸酯的简便两组分大环化反应的化学方法。从含有两个谷氨酸γ-酰肼残基的肽开始，可以很容易地获得异氰酸酯，并与二羧酸的酰肼环化。亲核连接基团的选择允许轻松调节大环肽的生化性质。使用所描述的方法合成了四个环状 NYAD-1 类似物，并显示出一系列的生物活性。
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