Digal Lori D, Kirkeby Emily K, Austin Maxwell J, Roberts Andrew G
Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States.
ACS Omega. 2023 Feb 27;8(10):9319-9325. doi: 10.1021/acsomega.2c07586. eCollection 2023 Mar 14.
Progress toward the design and synthesis of ambiphilic aryl thiol-iminium-based small molecules for organocatalyzed thioacyl aminolysis is reported. Here we describe the synthesis of a novel tetrahydroisoquinoline-derived scaffold, bearing both thiol and iminium functionalities, capable of promoting the transthioesterification and subsequent amine capture reactions necessary to achieve organocatalyzed thioacyl aminolysis. Model studies demonstrate the ability of this designed organocatalyst to deliver critical intermediates capable of undergoing these individual reactions necessary for the proposed process. Future design improvements and directions toward cysteine-independent organocatalyzed native chemical ligation are discussed.
报道了用于有机催化硫酰氨解的双亲性芳基硫醇-亚胺鎓基小分子的设计与合成进展。在此，我们描述了一种新型四氢异喹啉衍生支架的合成，该支架同时具有硫醇和亚胺鎓功能，能够促进实现有机催化硫酰氨解所需的转硫酯反应及后续胺捕获反应。模型研究证明了这种设计的有机催化剂能够提供关键中间体，这些中间体能够进行所提出过程所需的这些单独反应。还讨论了未来设计改进以及朝着不依赖半胱氨酸的有机催化天然化学连接的方向。
