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, AssuntaMembro del Collaboration Group
;Pierri, GiovanniMembro del Collaboration Group
;Costabile, ChiaraMembro del Collaboration Group
;Della Sala, GiorgioMembro del Collaboration Group
;Tedesco, ConsigliaMembro del Collaboration Group
;Izzo, IreneMembro 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.File in questo prodotto:
File | Dimensione | Formato | |
---|---|---|---|
PREPRINT OL 2018 DE RICCARDIS_ct.pdf
accesso aperto
Descrizione: Articolo principale
Tipologia:
Documento in Pre-print (manoscritto inviato all'editore, precedente alla peer review)
Licenza:
Creative commons
Dimensione
950.58 kB
Formato
Adobe PDF
|
950.58 kB | Adobe PDF | Visualizza/Apri |
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.