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Rapid and convenient semi-automated microwave-assisted solid-phase synthesis of arylopeptoids |
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| Authors: | Jakob Ewald Rasmussen Marcello Massimo Boccia John Nielsen Claude Taillefumier Sophie Faure Thomas Hjelmgaard |
| Institution: | 1. Department of Chemistry, Section for Chemical Biology and Nanobioscience, Faculty of Science, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark;2. Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen, Denmark;3. CNRS, UMR 6296, ICCF, BP 80026, 63171 Aubière, France;4. Clermont Université, Université Blaise Pascal, Institut de Chimie de Clermont-Ferrand, BP 10448, 63000 Clermont-Ferrand, France |
| Abstract: | A facile and expedient route to the synthesis of arylopeptoid oligomers (N-alkylated aminomethyl benz-amides) using semi-automated microwave-assisted solid-phase synthesis is presented. The synthesis was optimized for the incorporation of side chains derived from sterically hindered or unreactive amines and both ortho- and para-substituted arylo-backbones. By utilizing this optimized protocol a complex nonameric arylopeptoid was synthesized in less than 11 h, featuring a novel alternating ortho-, meta-, and para-substituted backbone pattern and a variety of chemically diverse and challenging side chains. |
| Keywords: | Aromatic oligoamides Solid-phase synthesis Automated synthesis Microwave-assisted synthesis Submonomer synthesis |
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