Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Xiaodong Shi; Yinghuan Liu; Rongtong Zhao; Zigang Li

doi:10.3791/57356

利用光致硫醇-烯/yne Hydrothiolation 构造硫醚类/乙烯基硫化物栓系螺旋肽

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JoVE Journal Chemistry

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

利用光致硫醇-烯/yne Hydrothiolation 构造硫醚类/乙烯基硫化物栓系螺旋肽

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11:09 min

August 1, 2018

DOI: 10.3791/57356-v

Xiaodong Shi*¹, Yinghuan Liu*¹, Rongtong Zhao¹, Zigang Li¹

¹Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology,Peking University Shenzhen Graduate School

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本文提出了一种利用光致硫醇烯/硫醇-yne hydrothiolation 构建硫醚类/乙烯基硫化物栓系螺旋肽的协议。

由于使用了硫代-烯或硫代-炔酮点击化学，这些方法简化了硫醚-栓系环肽的生成，具有优异的官能团耐受性和良好的产量。该技术的主要优点是硫醚系绳提供了一个无痕修饰位点，在肽合成修饰后显着扩展了稳定肽的化学空间。要开始该程序，通过三通旋塞阀将装有 50 毫克 Rink Amide MBHA 填料的色谱柱连接到台式真空歧管和氮气或氩气管路上。

在树脂床中加入 1 至 2 毫升二氯甲烷，然后用惰性气泡流轻轻搅拌混合物 10 分钟，使树脂膨胀。完成后，用橡胶移液器灯泡排干树脂。然后，向树脂中加入 1 至 2 mL N 端 Fmoc 脱保护溶液。

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