Yan Tao, Feringa Ben L, Barta Katalin
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, Netherlands.
Sci Adv. 2017 Dec 8;3(12):eaao6494. doi: 10.1126/sciadv.aao6494. eCollection 2017 Dec.
-alkyl amino acids find widespread application as highly valuable, renewable building blocks. However, traditional synthesis methodologies to obtain these suffer from serious limitations, providing a major challenge to develop sustainable alternatives. We report the first powerful catalytic strategy for the direct N-alkylation of unprotected α-amino acids with alcohols. This method is highly selective, produces water as the only side product leading to a simple purification procedure, and a variety of α-amino acids are mono- or di-N-alkylated, in most cases with excellent retention of optical purity. The hydrophobicity of the products is tunable, and even simple peptides are selectively alkylated. An iron-catalyzed route to mono--alkyl amino acids using renewable fatty alcohols is also described that represents an ideal green transformation for obtaining fully bio-based surfactants.
烷基氨基酸作为极有价值的可再生结构单元有着广泛的应用。然而，传统的合成这些物质的方法存在严重局限性，这对开发可持续的替代方法构成了重大挑战。我们报道了首个用于未保护的α-氨基酸与醇直接N-烷基化的高效催化策略。该方法具有高度选择性，仅产生水作为唯一的副产物，从而使得纯化过程简单，并且多种α-氨基酸能够进行单-N-烷基化或双-N-烷基化，在大多数情况下能出色地保持光学纯度。产物的疏水性是可调节的，甚至简单的肽也能被选择性烷基化。还描述了一种使用可再生脂肪醇通过铁催化制备单烷基氨基酸的路线，这是获得完全基于生物的表面活性剂的理想绿色转化方法。
