title: Synthesis of chiral five-membered carbocyclic ring amino acids with an acetal moiety and helical conformations of its homo-chiral homopeptides.
abstract: Chiral five-membered carbocyclic ring amino acids bearing various diol acetal moieties were synthesized starting from l-malic acid, and homo-chiral homopeptides composed of cyclic amino acid (S)-Ac5 c(3EG) bearing an ethylene glycol acetal, up to an octapeptide, were prepared. A conformational analysis revealed that (S)-Ac5 c(3EG) homopeptides formed helical structures. (S)-Ac5 c(3EG) homopeptides, up to hexapeptides, formed helical structures without controlling the helical screw direction, while (S)-Ac5 c(3EG) hepta- and octapeptides formed helical structures with a preference for the left-handed (M) helical-screw direction. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 106: 555-562, 2016.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki, 852-8521, Japan.
authors.forename: Yurie
authors.initials: Y
authors.lastname: Koba
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki, 852-8521, Japan.
authors.forename: Yoko
authors.initials: Y
authors.lastname: Hirata
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki, 852-8521, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Ueda
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki, 852-8521, Japan.
authors.forename: Makoto
authors.initials: M
authors.lastname: Oba
authors.affiliation: Osaka University of Pharmaceutical Sciences, Osaka, 569-1094, Japan.
authors.forename: Mitsunobu
authors.initials: M
authors.lastname: Doi
authors.affiliation: Division of Organic Chemistry, National Institute of Health Sciences, Tokyo, 158-8501, Japan.
authors.forename: Yosuke
authors.initials: Y
authors.lastname: Demizu
authors.affiliation: Division of Organic Chemistry, National Institute of Health Sciences, Tokyo, 158-8501, Japan.
authors.forename: Masaaki
authors.initials: M
authors.lastname: Kurihara
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki, 852-8521, Japan.
authors.forename: Masakazu
authors.initials: M
authors.lastname: Tanaka
mesh_terms: D000598:Amino Acids, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D019855:Ethylene Glycol / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D017433:Protein Structure, Secondary
chemical_list: D000598:Amino Acids, Cyclic; D010455:Peptides; D019855:Ethylene Glycol
keywords: conformation; cyclic amino acid; helix; homopeptide; α,α-disubstituted amino acid