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Umpolung reactivity in amide and peptide synthesis

机译：酰胺和肽合成中的反应活性

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摘要

The amide bond is one of nature's most common functional and structural elements, as the backbones of all natural peptides and proteins are composed of amide bonds. Amides are also present in many therapeutic small molecules. The construction of amide bonds using available methods relies principally on dehydrative approaches, although oxidative and radical-based methods are representative alternatives. In nearly every example, carbon and nitrogen bear electrophilic and nucleophilic character, respectively, during the carbon-nitrogen bond-forming step. Here we show that activation of amines and nitroalkanes with an electrophilic iodine source can lead directly to amide products. Preliminary observations support a mechanism in which the polarities of the two reactants are reversed (German, umpolung) during carbon-nitrogen bond formation relative to traditional approaches. The use of nitroalkanes as acyl anion equivalents provides a conceptually innovative approach to amide and peptide synthesis, and one that might ultimately provide for efficient peptide synthesis that is fully reliant on enantioselective methods.
机译：酰胺键是自然界中最常见的功能和结构元件之一，因为所有天然肽和蛋白质的骨架均由酰胺键组成。酰胺还存在于许多治疗性小分子中。尽管氧化和基于自由基的方法是代表性的选择，但是使用可用方法构造酰胺键主要依赖于脱水方法。在几乎每个示例中，碳和氮在形成碳氮键的步骤中分别具有亲电和亲核特性。在这里，我们表明用亲电子碘源活化胺和硝基烷烃可直接导致酰胺产物。初步观察结果表明，相对于传统方法而言，在形成碳氮键的过程中，两种反应物的极性都发生了逆转（德国人，物质保护）。使用硝基烷烃作为酰基阴离子当量为酰胺和肽的合成提供了一种概念上创新的方法，并且最终可能提供完全依赖于对映选择性方法的有效肽合成方法。

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  • 来源
    《Nature》 |2010年第7301期|P.1027-1032|共6页
  • 作者

    Bo Shen; Dawn M. Makley; Jeffrey N. Johnston;

  • 作者单位

    Department of Chemistry, Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA;

    Department of Chemistry, Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA;

    Department of Chemistry, Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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