Highly Convenient Gram-Scale Solution-Phase Peptoid Synthesis and Orthogonal Side-Chain Post-Modification

Abstract

This paper describes the development of a highly convenient solution-phase methodology using volatile amines for the synthesis of β-, α,β- and α-tetrapeptoids, as an alternative to solid-phase technologies. Column chromatographic purifications are reduced to a minimum and the majority of the intermediates are purified by filtration and/or evaporation. The method is amenable to gram-scale synthesis of peptoids, and post-modification of a model peptoid by successive and selective ligations, using click thiol-ene coupling, and copper-catalysed azide-alkyne cycloaddition is demonstrated.

peptoids - oligomers - gram-scale synthesis - thiol-ene coupling - cycloaddition - post-modifications

References

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Present address: Faculty of Life Sciences, IGM, Section for Bioorganic Chemistry, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark. Email: [e-mail].

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