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Researchers Simone Pilon, Steen Ingemann Jørgsenen and Jan van Maarseveen of the research group Synthetic Organic Chemistry have developed a novel approach to the synthesis of mechanically interlocked peptidic products. In a paper just accepted by ACS Organic&Inorganic, they present an ester-functionalized, aromatic δ-amino acid as a versatile central covalent templating unit, and show how this is capable of producing both a catenane and a rotaxane from the same multimacrocyclic intermediate.

Graphical abstract
Image: HIMS.

Abstract

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.

Paper

Simone Pilon, Steen Ingemann Jørgensen, and Jan H. van Maarseveen: Covalent [2]Catenane and [2]Rotaxane Synthesis via a δ-Amino Acid Template. ACS Org. Inorg. Au Publication Date: August 11, 2021, DOI: 10.1021/acsorginorgau.1c00017