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Issue 32, 2019
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A study of the cistrans isomerization preference of N-alkylated peptides containing phosphorus in the side chain and backbone

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Abstract

The current work provides a study on the cistrans isomerization behaviour of N-alkylated peptides decorated with phosphonate ester groups. A Ugi four-component reaction was chosen for the synthesis of N-alkylated peptides, where almost only the cis isomer was detected when the phosphonate ester group was incorporated as an amine component in the side chain. However, the phosphonate ester group inserted in the backbone, as an isocyanide component, leads preferably to the trans isomer of this kind of peptides. The diverse behaviour of cistrans isomerization has been explained via spectroscopic nuclear magnetic resonance analysis and computational calculations.

Graphical abstract: A study of the cis–trans isomerization preference of N-alkylated peptides containing phosphorus in the side chain and backbone

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Supplementary files

Article information


Submitted
30 Apr 2019
Accepted
20 Jul 2019
First published
23 Jul 2019

New J. Chem., 2019,43, 12804-12813
Article type
Paper

A study of the cistrans isomerization preference of N-alkylated peptides containing phosphorus in the side chain and backbone

A. F. de la Torre, A. Ali, O. Concepcion, A. L. Montero-Alejo, F. M. Muñiz, C. A. Jiménez, J. Belmar, J. L. Velázquez-Libera, E. W. Hernández-Rodríguez and J. Caballero, New J. Chem., 2019, 43, 12804
DOI: 10.1039/C9NJ02234A

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