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Preparation of cyclic peptide libraries using intramolecular oxime formation
Kade D Roberts1, John N Lambert, Nicholas J Ede
1School of Chemistry, The University of Melbourne, Grattan Street, Parkville, Victoria 3010, Australia. kade.roberts@ludwig.edu.au
Summary
A novel cyclization method creates cyclic peptide libraries using C-terminal ketones and N-terminal hydroxylamines. This approach efficiently synthesizes macrocyclic oximes, yielding mixtures of syn and anti isomers.
Area of Science:
- Medicinal Chemistry
- Organic Synthesis
- Peptide Chemistry
Background:
- Cyclic peptides are crucial in drug discovery due to their enhanced stability and bioavailability.
- Developing efficient synthetic routes for diverse cyclic peptide libraries remains a challenge.
Purpose of the Study:
- To introduce a new synthetic methodology for constructing cyclic head-to-side chain peptide libraries.
- To utilize a novel key cyclization step involving oxime formation.
Main Methods:
- The synthesis involves a key cyclization step reacting a C-terminal ketone with an N-terminal hydroxylamine.
- This reaction forms a macrocyclic oxime linkage, enabling library synthesis.
Main Results:
- The developed methodology efficiently produces cyclic peptide products.
- The resulting cyclic peptides are obtained as mixtures of syn and anti oxime isomers.
Conclusions:
- This novel method provides an efficient route to cyclic head-to-side chain peptide libraries.
- The oxime-based cyclization is a versatile strategy for generating diverse cyclic peptide scaffolds.