School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.
School of Biological Sciences, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.
J Am Chem Soc. 2024 Nov 6;146(44):30009-30013. doi: 10.1021/jacs.4c12210. Epub 2024 Oct 23.
We describe the enzymatic bromination of ribosomally synthesized peptides and develop protocols for Sonogashira coupling of peptidic aryl bromides with a panel of alkynes. Using this workflow, entirely new chemical handles are introduced onto ribosomal peptides, including but not limited to terminal alkynes, which enable further diversification via alkyne-azide click chemistry. Regiospecific enzymatic installation of the aryl bromide circumvents genetic code expansion and passivation of other reactive handles on the peptide chain, representing the applicability of biocatalysts in peptide modification chemistry.
我们描述了核糖体合成肽的酶促溴化作用，并开发了 Sonogashira 偶联反应的方案，用于将肽基芳基溴化物与一系列炔烃偶联。使用此工作流程，可将全新的化学基团引入核糖体肽中，包括但不限于末端炔烃，这可通过炔烃-叠氮点击化学进一步多样化。芳基溴的区域特异性酶促安装避免了遗传密码扩展和肽链上其他反应性基团的失活，这代表了生物催化剂在肽修饰化学中的适用性。
