Chiral induction was utilized for the synthesis of diastereopure cyclic peptoids containing an N-benzyl alanine residue. Molecular modeling, NMR spectroscopy, single-crystal X-ray diffraction studies, and HPLC with chiral stationary phase demonstrated easy formation of free and sodium/benzylammonium complexed cyclic oligomers through strategic incorporation of a single stereogenic center in the oligomeric backbone. The synthesis of cyclic peptoids with defined conformational chirality and appropriate side chain topology is now possible.

Cyclic Peptoids as Topological Templates: Synthesis via Central to Conformational Chirality Induction

D'Amato, Assunta
Membro del Collaboration Group
;
Pierri, Giovanni
Membro del Collaboration Group
;
Costabile, Chiara
Membro del Collaboration Group
;
Della Sala, Giorgio
Membro del Collaboration Group
;
Tedesco, Consiglia
Membro del Collaboration Group
;
Izzo, Irene
Membro del Collaboration Group
;
De Riccardis, Francesco
2018

Abstract

Chiral induction was utilized for the synthesis of diastereopure cyclic peptoids containing an N-benzyl alanine residue. Molecular modeling, NMR spectroscopy, single-crystal X-ray diffraction studies, and HPLC with chiral stationary phase demonstrated easy formation of free and sodium/benzylammonium complexed cyclic oligomers through strategic incorporation of a single stereogenic center in the oligomeric backbone. The synthesis of cyclic peptoids with defined conformational chirality and appropriate side chain topology is now possible.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4704223
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