L.H. thanks the following institutions for funding: The University of Sydney (Postdoctoral Research Fellowship), UNSW Australia (Faculty of Science Research Grant), and the Australian Research Council (Discovery Early Career Researcher Award).
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Communication
Stereoselective Fluorination Alters the Geometry of a Cyclic Peptide: Exploration of Backbone-Fluorinated Analogues of Unguisin A†
Version of Record online: 21 MAY 2014
DOI: 10.1002/anie.201403071
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Hu, X.-G., Thomas, D. S., Griffith, R. and Hunter, L. (2014), Stereoselective Fluorination Alters the Geometry of a Cyclic Peptide: Exploration of Backbone-Fluorinated Analogues of Unguisin A. Angew. Chem. Int. Ed., 53: 6176–6179. doi: 10.1002/anie.201403071
- †
Publication History
- Issue online: 5 JUN 2014
- Version of Record online: 21 MAY 2014
- Manuscript Revised: 4 APR 2014
- Manuscript Received: 9 MAR 2014
Funded by
- Australian Research Council
Keywords:
- conformation analysis;
- cyclic peptides;
- gauche effect;
- NMR spectroscopy;
- stereoselective fluorination
Abstract
New methods for enhancing the efficiency of peptide cyclization, and for fine-tuning the conformations of cyclic peptides, are valuable from a drug development perspective. Herein stereoselective fluorination is investigated as a new strategy for achieving these goals. Four vicinal difluorinated analogues of the natural cyclic heptapeptide unguisin A have been efficiently synthesized. The analogues are found to adopt dramatically different secondary structures, controlled by the fluorine stereochemistry.
