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A spirocyclic backbone accesses new conformational space in an extended, dipole-stabilized foldamer
William Edward Roe1, Toyah Mary Catherine Warnock1, Peter Clarke Knipe2
1School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Belfast, BT9 5AG, UK.
Communications Chemistry
|April 17, 2023
Summary
Researchers developed a novel foldamer with spiro bis-lactams for controlled backbone rotation. This innovation allows precise shape control, enabling complex structures and enhanced functions in hybrid foldamer designs.
Area of Science:
- Supramolecular Chemistry
- Organic Chemistry
- Materials Science
Background:
- Aromatic foldamers typically exhibit limited conformational flexibility, restricting their structural complexity and functional potential.
- Existing foldamer designs often lack precise control over secondary and tertiary structure formation.
Purpose of the Study:
- To introduce a novel method for controlling foldamer conformation using spiro bis-lactams.
- To enable precise manipulation of foldamer shape along orthogonal axes for advanced structural designs.
- To explore the formation of complex hetero-oligomers with enhanced functionalities.
Main Methods:
- Iterative synthesis of foldamers incorporating spiro bis-lactam units.
- Utilized X-ray diffraction (XRD), Nuclear Magnetic Resonance (NMR) spectroscopy, and computational modeling.
- Investigated the conformational properties of synthesized homo- and hetero-oligomers.
Main Results:
- Spiro bis-lactams facilitate controlled backbone rotation, enabling precise shape control akin to yaw and roll axes.
- Homo-oligomers adopt an extended right-handed helix with a pitch comparable to B-DNA (>30 Å).
- Demonstrated compatibility with existing foldamers for creating structurally complex hetero-oligomers.
Conclusions:
- The incorporation of spiro bis-lactams significantly enhances foldamer conformational control and structural diversity.
- This approach opens new avenues for designing sophisticated hybrid foldamers with tailored functions.
- The developed foldamers offer a versatile platform for advanced applications in molecular design and nanotechnology.
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