Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 36, Pages 9450-9455Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402789
Keywords
cyclic peptides; cyclization; peptide NMR spectroscopy; peptide synthesis; peptides
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Funding
- European Research Council/ERC [203413]
- Minerva Center for Bio-Hybrid complex systems
- PBC fellowship, Council of Higher Education, Israel
- European Research Council (ERC) [203413] Funding Source: European Research Council (ERC)
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We present a new approach for peptide cyclization during solid phase synthesis under highly acidic conditions. Our approach involves simultaneous in situ deprotection, cyclization and trifluoroacetic acid (TFA) cleavage of the peptide, which is achieved by forming an amide bond between a lysine side chain and a succinic acid linker at the peptide N-terminus. The reaction proceeds via a highly active succinimide intermediate, which was isolated and characterized. The structure of a model cyclic peptide was solved by NMR spectroscopy. Theoretical calculations support the proposed mechanism of cyclization. Our new methodology is applicable for the formation of macrocycles in solid-phase synthesis of peptides and organic molecules.
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