Pseudo-Ring Methodology to Control the Conformations of Macrocyclic Peptides.

Chemistry

Davenport Research Laboratories, University of Toronto, 80 St. George St, Toronto, Ontario, M5S 3H6, Canada.

Published: April 2025


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Article Abstract

A pseudo-ring is a medium-sized cyclic structure, held together by a strong hydrogen bond, that can act as a mimetic of a covalently linked heterocycle. Molecules that contain pseudo-rings can switch between "open" and "closed" forms. This paper examines the utility of pseudo-ring constructs to control conformations and properties of macrocycles. The spectroscopic evidence suggests that the "open" and "closed" pseudo-ring-containing macrocycles differ in their three-dimensional characteristics, which results in markedly different lipophilicities. The dynamic nature of pseudo-rings has led to the emergence of tunable fluorescence that should be useful in environment-sensitive applications.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC12043042PMC
http://dx.doi.org/10.1002/chem.202500581DOI Listing

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