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Flow-chemistry enabled efficient synthesis of β-peptides: backbone topology vs. helix formation

Author:
NekkaaThese authors contributed equally; IN: amino acid and peptide synthesis, DB: NMR and ECD part., Imane, Bogdán, Dóra, Gáti, Tamás, Béni, Szabolcs, Juhász, Tünde, Palkó, Márta, Paragi, Gábor, Tóth, Gábor K., Fülöp, Ferenc, Mándity, István M.
Source:
Chemical communications 2019 v.55 no.21 pp. 3061-3064
ISSN:
1364-548X
Subject:
chemical bonding, chemical compounds, chemical reactions, topology
Abstract:
Enantiodiscriminative helix formation was observed for β-peptide H14 helices. This observation is caused by the synperiplanar orientation of H–O atoms which is more unfavorable than those for H–H interaction. The 1,2 H–O interaction leads to the destruction of the helical structure. The introduction of a double C–C bond in the backbone rules out helix formation.
Agid:
6316306