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

Org Biomol Chem. 2020 Jul 15;18(27):5203-5209. doi: 10.1039/d0ob01190h.

Abstract

The rapid synthesis of an amide hydrogen bond templated [1]rotaxane is reported - demonstrating a potential pathway to synthetic analogues of lasso peptides. The structures of the [1]rotaxane and its unthreaded isomer have been characterized by NMR spectroscopy and modelled using DFT calculations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Density Functional Theory
  • Hydrogen Bonding
  • Molecular Mimicry
  • Nerve Tissue Proteins / chemistry*
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides / chemistry*
  • Rats
  • Rotaxanes / chemistry*

Substances

  • Nerve Tissue Proteins
  • Peptides
  • Rotaxanes