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Synthesis 2011(2): 257-264  
DOI: 10.1055/s-0030-1258351
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Cécile Caumesa, Thomas Hjelmgaard*a,b,1, Roland Remusona,b, Sophie Faure*a,b, Claude Taillefumiera,b
a Clermont Université, Université Blaise Pascal, Laboratoire SEESIB, BP 10448, 63000 Clermont-Ferrand, France
b CNRS, UMR 6504, Laboratoire SEESIB, 63177 Aubière Cedex, France
Fax: +33(4)73407717; e-Mail: claude.taillefumier@univ-bpclermont.fr; e-Mail: sophie.faure@univ-bpclermont.fr;
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Publication History

Received 1 September 2010
Publication Date:
03 December 2010 (online)

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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.

Key words

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

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1

Present address: Faculty of Life Sciences, IGM, Section for Bioorganic Chemistry, University of Copenhagen, Thorvaldsensvej 40, 1871 Frederiksberg C, Denmark. Email: thhj@life.ku.dk.