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Enzymatic Ugi Reaction with Amines and Cyclic Imines

机译:与胺和环状亚胺的酶促尿嘧啶反应

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The application of the Ugi reaction to the construction of new peptide scaffolds is an important goal of organic chemistry. To date, there are no examples of the Ugi reaction being performed with a cyclic imine and amine simultaneously. The application of 2-substituted cyclic imines in an enzymatic three-component Ugi-type reaction provides an elegant and attractive synthesis of substituted pyrrolidine and piperidine derivatives in up to 60% yield. Results on studies of the selection of an enzyme, amount of water, and solvent used in a novel three-component Ugi reaction and the limitations thereof are reported herein. The presented methodology exploiting enzyme promiscuity in the multicomponent reaction fulfills the requirements associated with green chemistry. Several methods, such as isotope labeling and enzyme inhibition, were used to probe the possible mechanism of this complex synthesis. This research is the first example of an enzyme-catalyzed Ugi-type reaction with an imine, amine, and isocyanide.
机译:Ugi反应在新型肽支架构建中的应用是有机化学的重要目标。迄今为止,还没有使用环状亚胺和胺同时进行Ugi反应的例子。将2-取代的环状亚胺用于酶促三组分Ugi型反应中,可以以高达60%的收率优雅,诱人地合成取代的吡咯烷和哌啶衍生物。本文报道了在新型三组分Ugi反应中使用的酶的选择,水和溶剂的选择及其限制的研究结果。提出的在多组分反应中利用酶混杂的方法学满足了与绿色化学相关的要求。几种方法,例如同位素标记和酶抑制,被用来探测这种复杂合成的可能机制。这项研究是与亚胺,胺和异氰酸酯进行酶催化的Ugi型反应的第一个实例。

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