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Accueil du site > Équipes de recherche > Chimie Organique et Médicinale > Peptoid > Thèmes de recherche > Macrocyclic peptoids

Macrocyclic peptoids

Cyclic β-peptoids

The first synthesis of functionalized β-peptoid macrocycles was performed. X-ray crystallographic structure of a tetramer reveals a C2-symmetrical derivative with unexpected all-cis-amide bonds and spatial disposition of the appendages toward the two opposite faces of the ring. These macrocycles constitute novel promising templates for multimeric ligation of biologically active ligands. The concept was exemplified by chemical decoration of the cyclic tetramer via multivalent CuAAC reactions.

Cyclic β-peptoids.
Roy O., Faure S., Thery V., Didierjean C., Taillefumier C. Org. Lett. 2008, 10, 921-924.

Cyclic α,β-peptoids

The comparison of the crystal structures of a cyclic α,β-tetramer and a cyclic α,β-octamer reveals striking similarities. Indeed, both structures have the presence of two αtrans-βcis segments in a turn-like conformation in common. The fact that this specific conformation is also present in an unconstrained cyclic octamer, having a different side chain sequence, suggests that the observed turn may represent a privileged conformation of the α,β-peptoid family.

Cyclic α,β-peptoid octamers with differing side chain patterns : synthesis and conformational investigation.
De Santis E., Hjelmgaard T., Faure S., Roy O., Didierjean C,. Alexander B.D., Siligardi G., Hussain R., Javorfi T., Edwards A.A., Taillefumier C. Amino Acids 2011, 41, 663-672.
Cyclic α,β-Tetrapeptoids : Sequence-Dependent Cyclization And Conformational Preference
Caumes C., Fernandes C., Roy O., Hjelmgaard T., Wenger E., Didierjean C., Taillefumier C., Faure S. Org. Lett. 2013, 15, 3626-3629.

Cyclic arylopeptoids

The head-to-tail conversion of linear arylopeptoids (oligomeric N-substituted aminomethyl benzamides) into the derived novel macrocycles has enabled the first X-ray structures of arylopeptoid constructs and the identification of well-defined architectures in solution.

Macrocyclic Arylopeptoids – A Novel Type Of Cyclic N-Alkylated Aromatic Oligoamides Forming Nanotubular Assemblies
Hjelmgaard T., Roy O., Nauton L., El-Ghozzi M., Avignant D., Didierjean C., Taillefumier C., Faure S. Chem. Commun. 2014, 50, 3564-3567.