Organic and Biomimetic Chemistry Research Group, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 (S4), 9000, Ghent, Belgium.
Chemistry. 2020 Apr 9;26(21):4701-4705. doi: 10.1002/chem.202000434. Epub 2020 Mar 18.
Handling of the individual fragments remains a bottleneck in the convergent assembly of peptides. Overlooked since the emergence of ligation chemistries during the past two decades, so-called resin-to-resin transfer reactions (RRTR) are here described as a strategic shortcut in this context. Condensation of the involved moieties at an acceptor resin is facilitated by shuttling peptide segments directly from a donor resin in a one-pot fashion. The straightforward synthesis of a sterically constrained 13-mer peptidosteroid model illustrates the utility of this approach, presenting the first successful application of the RRTR methodology in the field of multivalent design and bioconjugation. Relying on established procedures to generate, monitor and isolate intermediates and products, the solid-phase nature of the entire strategy allows for the fast construction of polypeptide adducts and libraries thereof. As such, a rejuvenated use and new opportunities for RRTR are reported.
在肽的汇聚组装中，各个片段的处理仍然是一个瓶颈。在过去二十年的连接化学出现以来，这种所谓的树脂到树脂转移反应（RRTR）一直被忽视，在这里被描述为这种情况下的一种战略捷径。通过将肽段直接从供体树脂一锅法转移到受体树脂上，促进了相关部分在受体树脂上的缩合。通过这种方法，刚性约束的 13 肽甾体模型的简单合成说明了这种方法的实用性，这是 RRTR 方法在多价设计和生物缀合领域的首次成功应用。通过建立生成、监测和分离中间体和产物的既定程序，整个策略的固相性质允许快速构建多肽加合物及其文库。因此，报告了 RRTR 的复兴使用和新机会。
