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N-Substituted arylsulfonamide building blocks as alternative submonomers for peptoid synthesis
- Vézina-Dawod, Simon, Derson, Antoine, Biron, Eric
- Tetrahedron letters 2015 v.56 no.2 pp. 382-385
- N-substituted glycines, amino alcohols, chemical structure, hydroxylation, medicinal properties
- Peptoids (oligo N-substituted glycines) are peptidomimetic oligomers showing attractive structural and pharmacological properties. The efficiency of their synthesis has prompted the use of peptoids in combinatorial libraries. To increase the chemical diversity accessible in peptoid design and libraries, we demonstrate here that N-substituted o-nitrobenzenesulfonamide derivatives can be used as alternative building blocks in the synthesis of peptoids by the submonomer approach. The preparation of N,O-protected amino alcohol submonomers and the conditions for their incorporation into peptoid oligomers are reported. The described method is compatible with the submonomer approach and was applied to prepare peptoid oligomers bearing different hydroxylated side chains.