An amide hydrogen bond templated [1]rotaxane displaying a peptide motif – demonstrating an expedient route to synthetic mimics of lasso peptides

Abstract

The rapid synthesis and characterization of an amide hydrogen bond templated [1]rotaxane – demonstrating a potential pathway to synthetic analogues of lasso peptides.

The Mobility of Homomeric Lasso‐ and Daisy Chain‐Like Rotaxanes in Solution and in the Gas Phase as a Means to Study Structure and Switching Behaviour

“…Evans and coworkers also employed the DOSY technique to differentiate between two species which are only distinguishable from each other by the existence or absence of a mechanical bond, [1]rotaxane 12 and macrocycle 13 [23] . The D values measured in DMSO‐ d 6 were 1.28×10 −10 m 2 s −1 for 12 (Figure 6a) and 1.10×10 −10 m 2 s −1 for 13 (Figure 6b), which are in fully good agreement with the DFT simulated structures of the monomeric intertwined and non‐intertwined forms.…”

Post‐Synthetic Macrocyclization of Rotaxane Building Blocks

“…Evans reported in 2020 the synthesis of the peptide [1] rotaxane 51 bearing amide bonds at both macrocycle and thread using more classical peptide chemical coupling methods (Scheme 13b). [62] Pre-assembled [2]rotaxane 50 was subjected to simultaneous deprotections of (1) the N-terminal side of the glycylglycylglycine sequence that substitutes the macrocycle and ( 2) the tert-butyl ester belonging to the glycine residue at the extremity of the encircled axle. Noteworthy, preservation of the interlocked architecture in 50 was ensured by the 1,3,5 substitution of the two trifluoromethylbenzamide moieties.…”

Pillar[5]arene-based [1]rotaxanes with salicylaldimine as the stopper: synthesis, characterization and application in the fluorescence turn-on sensing of Zn2+ in water

“…[1][2][3][4] [1]Rotaxanes refer to a classical type of MIM that consists of a ring-shaped macrocyclic wheel sheathed on its own linear axle, with the wheel and axle parts being linked by covalent bonds. 5,6 So far, numerous reports have been made on the design and preparation of macrocycle-based [1]rotaxanes. [7][8][9][10] For instance, Yan et al reported a novel method to prepare B21C7-based [1]rotaxanes.…”