1313876-83-3Relevant articles and documents
Cyclic α,α-Disubstituted α-Amino Acids with Menthone in Their Side-Chains Linked through an Acetal Moiety and Helical Structures of Their Peptides
Furukawa, Kaori,Oba, Makoto,Opiyo, George Ouma,Doi, Mitsunobu,Tanaka, Masakazu
, p. 2988 - 2998 (2016/07/11)
The chiral cyclic α,α-disubstituted α-amino acids, Hms[(–)-Men] and Hms[(+)-Men] with (–)- and (+)-menthones in their side-chains, respectively, were designed and synthesized. Hms[(–)-Men] homopeptides and Hms[(–)/(+)-Men]-containing l-Leu-based peptides were prepared in order to investigate the conformational properties of Hms[(–)/(+)-Men]. The preferred conformations of the Hms[(–)/(+)-Men]-containing peptides were determined by FTIR,1H NMR, and CD spectroscopy in solution, and by X-ray crystallographic analysis in the crystal state. Conformational analysis in solution revealed similar right-handed (P) 310-helical structures for the Hms[(–)/(+)-Men]-containing octapeptides. In the solid state of the hexapeptides, the peptide main-chain structures were mostly similar; however, some differences were observed in the side-chains. The Hms[(–)/(+)-Men] may function as helical inducers, but their side-chain chiralities had only a negligible effect on their helical-screw control of l-Leu-based peptides.
