Peptidines: glycine-amidine-based oligomers for solution- and solid-phase synthesis.
Julian Vastl1, Rendy Kartika2, Kichul Park3
1Department of Chemistry , Yale University , 225 Prospect Street , New Haven , CT 06511 , USA .
Chemical Science
|July 13, 2018
Summary
Researchers developed novel peptide-like oligomers called peptidines, which offer increased functionalization sites and reduced flexibility. These peptidines are synthesized using straightforward methods and show potential for drug discovery and peptide mimicry.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Medicinal Chemistry
Background:
- Biological oligomers like peptides and nucleic acids are crucial in nature and have inspired synthetic analogs.
- Existing peptidomimetics, such as peptoids, offer valuable platforms but have limitations in functionalization and flexibility.
Purpose of the Study:
- To introduce a new class of peptide-like oligomers, termed 'peptidines', with enhanced structural and functional properties.
- To explore the synthetic accessibility and conformational preferences of these novel peptidines.
Main Methods:
- Development of iterative solution- and solid-phase synthesis protocols for peptidines.
- Incorporation of diverse backbone and amidine substituents derived from primary and secondary amines.
- Crystallographic and computational studies to determine amidine geometry preferences.
Main Results:
- Peptidines were synthesized efficiently, featuring a functionalized N-atom replacing the carbonyl O-atom of poly-N-alkyl glycine oligomers.
- The amidine N-substituent doubles diversification sites per monomer and can decrease conformational flexibility compared to peptides and peptoids.
- Crystallographic and computational data revealed a strong preference for the trans (E) amidine geometry.
Conclusions:
- Peptidines represent a novel class of oligomers with high functional group density and straightforward synthetic preparation.
- Their unique properties make them promising candidates for generating molecular libraries, mimicking peptides, and identifying bioactive small molecules.
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