N-Substituted arylsulfonamide building blocks as alternative submonomers for peptoid synthesis

Authors: Vézina-Dawod, Simon; Derson, Antoine; Biron, Éric
Abstract: 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.
Keywords : Peptoids; Peptidomimetics; Solid-phase synthesis; Nitrobenzenesulfonamides
Document Type: Article de recherche
Issue Date: 8 January 2015
Open Access Date: 8 January 2017
Document version: AM
Permalink: http://hdl.handle.net/20.500.11794/880
This document was published in: Tetrahedron letters, Vol. 56 (2), 382–385 (2015)
http://dx.doi.org/10.1016/j.tetlet.2014.11.104
Elsevier
Alternative version: 10.1016/j.tetlet.2014.11.104
Collection:Articles publiés dans des revues avec comité de lecture

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