Extensive efforts are currently devoted to mimic the structure and functions of peptides and proteins with abiotic oligomers. Peptoids are a promising class of biomimetic oligomers composed of N-substituted glycines with enhanced proteolytic stability and permeability relative to peptides. Further modifications have involved the insertion of an additional methylene or an aryl group in the backbone. We have thus prepared two novel families of peptoids: the a,�-peptoids with alternating a- and �-residues and the arylopeptoids composed of aminomethylbenzoic acid monomers. The first part of the presentation will focus on the synthesis and conformational investigation of these novel families. The second part of the presentation will discuss on how to reduce the inherent flexibility of peptoids. The a,�-peptoids [1] and arylopeptoids[2] have been cyclized which allowed us to obtain several X-ray crystal structures. We have also developed novel peptoid side chains that are capable of inducing only cis peptoid amides.[3] These novel tools have also facilitated the crystallisation of several peptoid structures.[1]Caumes, C.; Fernandes, C.; Roy, O.; Hjelmgaard, T.; Wenger, E.; Didierjean, C.; Taillefumier, C.; Faure, S. Org.Lett. 2013  , 15, 3626.[2]Hjelmgaard, T.; Roy, O.; Nauton, L.; El-Ghozzi, M.; Avignant, D.; Didierjean, C.; Taillefumier, C.; Faure, S. Chem.Commun. 2014 , 50, 3564[3]Caumes, C.; Roy, O.; Faure, S.; Taillefumier, C. J.Am.Chem.Soc. 2012  , 134, 9553. Roy, O.; Caumes, C.; Esvan, Y.; Didierjean, C.; Faure, S.; Taillefumier, C. Org.Lett. 2013  , 15, 2246.

Linear and cyclic a,�-peptoids and arylopeptoids: Synthesis and conformational preference

248th National Meeting (2014)

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