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Issue 40, 2012
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A convenient synthesis of difficult medium-sized cyclic peptides by Staudinger mediated ring-closure

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Abstract

Novel, efficient and mild preparation of 7- and 8-membered cyclic di- and 10-membered cyclic tripeptides containing α-, β- or γ-amino acid residues is effected by a Staudinger-mediated ring closure. Medium-sized cyclic di- and tripeptides – recognized as difficult targets – were obtained in moderate to good yields according to a straightforward sequence. Empirical force-field calculations were undertaken to determine their conformational behaviors and showed high levels of similarity with X-ray results. A computational study at the B3LYP/6-31+G** level of theory afforded information regarding the impact of the sequence, ring-size and substitution on the activation barriers for the cyclization of azido peptide thioesters.

Graphical abstract: A convenient synthesis of difficult medium-sized cyclic peptides by Staudinger mediated ring-closure

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Publication details

The article was received on 22 May 2012, accepted on 22 Aug 2012 and first published on 23 Aug 2012


Article type: Communication
DOI: 10.1039/C2OB25996F
Citation: Org. Biomol. Chem., 2012,10, 8055-8058

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    A convenient synthesis of difficult medium-sized cyclic peptides by Staudinger mediated ring-closure

    K. Ha, J. M. Monbaliu, B. C. Williams, G. G. Pillai, C. E. Ocampo, M. Zeller, C. V. Stevens and A. R. Katritzky, Org. Biomol. Chem., 2012, 10, 8055
    DOI: 10.1039/C2OB25996F

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