Aucagne Vincent, Leigh David A
School of Chemistry, University of Edinburgh, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, UK.
Org Lett. 2006 Sep 28;8(20):4505-7. doi: 10.1021/ol061657d.
A methodology for the successive regiospecific "clicking" together of three components in one pot via two triazole linkages is reported. The protocol utilizes copper(I)-mediated alkyne-azide cycloaddition reactions combined with a silver(I)-catalyzed TMS-alkyne deprotection under mild hydroalcoholic conditions. We exemplify the approach with peptide-based components to illustrate its compatibility with polyfunctionalized biomolecules. The method constitutes a promising tool for peptide ligation. We also provide a procedure for directly using TMS-alkynes as the cycloaddition partner in classical "click" chemistry.
报道了一种通过两个三唑键在一锅法中连续区域特异性地将三个组分“点击”在一起的方法。该方案利用铜（I）介导的炔烃-叠氮环加成反应，并结合在温和的水醇条件下银（I）催化的TMS-炔烃脱保护反应。我们以基于肽的组分为例来说明该方法与多官能化生物分子的兼容性。该方法是肽连接的一种有前景的工具。我们还提供了一种在经典“点击”化学中直接使用TMS-炔烃作为环加成伙伴的程序。
