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J Org Chem. 2011 May 6;76(9):3166-73. doi: 10.1021/jo102598n. Epub 2011 Apr 15.

Giant macrolactams based on β-sheet peptides.

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  • 1Department of Chemistry, University of California, Irvine, Irvine, California 92697-2025, USA.

Abstract

This paper reports the use of natural amino acids, the tripeptide β-strand mimic Hao, and the β-turn mimic δ-linked ornithine to generate water-soluble 54-, 78-, and 102-membered-ring macrolactams. These giant macrocycles were efficiently prepared by synthesis of the corresponding protected linear peptides, followed by solution-phase cyclization and deprotection. The protected linear peptide precursors were synthesized on 2-chlorotrityl chloride resin by conventional Fmoc-based solid-phase peptide synthesis. Macrocyclization was typically performed using HCTU and N,N-diisopropylethylamine in DMF at ca. 0.5 mM concentration. The macrocycles were isolated in 13-45% overall yield after HPLC purification and lyophilization. 1D, 2D TOCSY, and 2D ROESY (1)H NMR studies of the 54- and 78-membered-ring macrolactams establish that these compounds fold to form β-sheet structures in aqueous solutions.

© 2011 American Chemical Society

PMID:
21452877
[PubMed - indexed for MEDLINE]
PMCID:
PMC3088102
Free PMC Article
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