Pilon Simone, Jørgensen Steen Ingemann, van Maarseveen Jan H
Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098XH Amsterdam, The Netherlands.
ACS Org Inorg Au. 2021 Dec 1;1(2):37-42. doi: 10.1021/acsorginorgau.1c00017. Epub 2021 Aug 11.
Despite the advances in the synthesis of mechanically interlocked molecules, a generally applicable approach to interlocked natural products, such as lasso peptides, is yet to be formulated. While amino acid sequences have been introduced into several rotaxanes, the key structural components have always been dictated by the method used for supramolecular preorganization. In this work, we report the use of an ester-functionalized, aromatic δ-amino acid as the central covalent templating unit in the synthesis of both a [2]catenane and a [2]rotaxane from the same multimacrocyclic intermediate. This represents a key step toward future synthetic peptide-based interlocked products.
尽管在机械互锁分子的合成方面取得了进展，但尚未制定出一种普遍适用的方法来合成互锁的天然产物，如套索肽。虽然氨基酸序列已被引入到几种轮烷中，但关键结构成分一直由用于超分子预组织的方法决定。在这项工作中，我们报告了使用酯官能化的芳香族δ-氨基酸作为中心共价模板单元，从同一多环大环中间体合成[2]连环烷和[2]轮烷。这代表了未来基于合成肽的互锁产物的关键一步。
