We thank the MICINN (CTQ2008-00763/BQU and BFU2008-02795), IRB Barcelona, the Generalitat de Catalunya (2009SGR 00901), and BCN Peptides S.A. for financial support. R.R. and P.M.-G. thank the MICINN for a doctoral fellowship. E.A. and M.J.M. thank the Consolider RNAREG (CSD2009-00080) for financial support.
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Communication
Fine-tuning the π–π Aromatic Interactions in Peptides: Somatostatin Analogues Containing Mesityl Alanine†
Article first published online: 9 DEC 2011
DOI: 10.1002/anie.201106406
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Martín-Gago, P., Gomez-Caminals, M., Ramón, R., Verdaguer, X., Martin-Malpartida, P., Aragón, E., Fernández-Carneado, J., Ponsati, B., López-Ruiz, P., Cortes, M. A., Colás, B., Macias, M. J. and Riera, A. (2012), Fine-tuning the π–π Aromatic Interactions in Peptides: Somatostatin Analogues Containing Mesityl Alanine. Angew. Chem. Int. Ed., 51: 1820–1825. doi: 10.1002/anie.201106406
- †
Publication History
- Issue published online: 14 FEB 2012
- Article first published online: 9 DEC 2011
- Manuscript Received: 9 SEP 2011
Funded by
- MICINN. Grant Numbers: CTQ2008-00763/BQU, BFU2008-02795
- IRB Barcelona
- Generalitat de Catalunya. Grant Number: 2009SGR 00901
- BCN Peptides S.A.
- Consolider RNAREG. Grant Number: CSD2009-00080
Keywords:
- conformation analysis;
- NMR spectroscopy;
- noncovalent interactions;
- peptides;
- drug design
Going through the motions: Somatostatin analogues having greater conformational rigidity than somatostatin have been prepared by substituting Phe residues in the native sequence with mesityl alanine (Msa; see structure). The analogues show high affinity for SSTR receptors, thus showing that fine-tuning of noncovalent interactions between amino acid side chains can modulate peptide affinity and selectivity.