Stereoselective Formation of Chiral Metallopeptides

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Abstract

Playing into our hands: The achiral bipyridine amino acid fluorenylmethyloxycarbonyl 5‐amino‐3‐oxapentanoic acid (Fmoc‐O1PenBpy‐OH) has been used for the solid‐phase synthesis of metallopeptides. Circular dichroism, molecular modeling, and NMR spectroscopic studies show that the chirality of the resulting metal complexes in aqueous solution is determined, and can thus be controlled, by the stereochemistry of one proline residue in the loop between the two coordinating O1PenBpy residues

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This is the peer reviewed version of the following article: Rama, G., Ardá, A., Maréchal, J., Gamba, I., Ishida, H., Jiménez‐Barbero, J., Vázquez, M. E. and Vázquez López, M. (2012), Stereoselective Formation of Chiral Metallopeptides. Chem. Eur. J., 18: 7030-7035, which has been published in final form at https://doi.org/10.1002/chem.201201036. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions

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Rama, G., Ardá, A. , Maréchal, J., Gamba, I., Ishida, H., Jiménez‐Barbero, J., Vázquez, M. E. and Vázquez López, M. (2012), Stereoselective Formation of Chiral Metallopeptides. Chem. Eur. J., 18: 7030-7035. doi:10.1002/chem.201201036

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Consolider Ingenio. Grant Number: CSD2007‐00006 Xunta de Galicia. Grant Numbers: INCITE09 209 084PR, GRC2010/12, PGIDIT08CSA‐047209PR PRESTO Program of JST Grant‐in‐Aid for Scientific Research (C) from the Ministry of Education, Culture, Sports, Science, and Technology. Grant Number: 21550163 International Iberian Nanotechnology Laboratory (INL)

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© 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving