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Imidazolidinone‐Tethered α‐Hydrazidopeptides – Synthesis and Conformational Investigation
Author(s) -
Amabili Paolo,
Calvaresi Matteo,
Martelli Gianluca,
Orena Mario,
Rinaldi Samuele,
Sgolastra Federica
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801427
Subject(s) - chemistry , intramolecular force , monomer , hydrogen bond , nuclear magnetic resonance spectroscopy , stereochemistry , crystallography , molecule , organic chemistry , polymer
N α ‐acylated β 2,3 ‐3‐azapeptides, or α‐hydrazidopeptides, of different lengths were synthesized starting from a conformationally restricted imidazolidinone‐tethered monomer. The preferential conformations of the oligomers were investigated by NMR and CD spectroscopy, supported by computational analysis. The experimental data clearly confirmed the tendency of these α‐hydrazidopeptides to fold into a zig‐zag (Z8) 8‐helix conformation, whose stability is length‐dependent, stabilized by the C=O(i) ··· H–N(i + 2) and N(i) ··· H–N(i + 1) intramolecular H‐bonding pattern, as well as by non‐standard C=O ··· H‐C hydrogen bonds.