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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
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Conformational isomerism in cyclic peptoids and its specification.
A D'Amato1, R Schettini, G Della Sala
1Department of Chemistry and Biology "A. Zambelli", University of Salerno, Via Giovanni Paolo II, 132, Fisciano, SA 84084, Italy. dericca@unisa.it.
Organic & Biomolecular Chemistry
|November 23, 2017
Summary
This study introduces planar chirality to define cyclic peptoid geometry, revealing conformational isomerism and chirality. Understanding these synthetic macrocycles is key for future applications in chiral technologies.
Area of Science:
- Synthetic Chemistry
- Structural Chemistry
- Chirality Studies
Background:
- Traditional peptoid structural analysis uses Ramachandran plots, offering limited insight into stereochemistry.
- Internal coordinates provide less intuitive understanding for peptoids with complex stereochemistry.
Purpose of the Study:
- To compile conformationally stable cyclic peptoids reported up to 2017.
- To propose a method for defining cyclic peptoid geometry using planar chirality.
- To investigate conformational isomerism and chirality in cyclic peptoids.
Main Methods:
- Compilation of cyclic peptoid structures.
- Application of planar chirality for geometric definition.
- NMR spectroscopy with chiral solvating agents.
- Analysis of X-ray crystallographic data.
Main Results:
- A comprehensive list of stable cyclic peptoids up to 2017.
- A novel method for describing geometric arrangement via planar chirality.
- Demonstration of conformational isomerism and chirality using spectroscopic and crystallographic evidence.
Conclusions:
- Planar chirality offers a more intuitive understanding of cyclic peptoid geometry.
- Conformational isomerism and chirality are significant features of these synthetic macrocycles.
- This framework is crucial for advancing peptoid applications in asymmetric synthesis and supramolecular chemistry.
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