title: Preparation and conformational analysis of C-glycosyl beta(2)- and beta/beta(2)-peptides.
abstract: Ten C-glycosyl beta(2)- and beta/beta(2)-peptides with three to eight amino acid residues have been prepared. Solution and solid-phase peptide syntheses were employed to assemble beta(2)-amino acids in which C-glycosylic substituents are attached to the C-2 position of beta-amino acids. Conformational analysis of the C-glycosyl beta(2)-peptides using NMR and CD spectra indicates that the tripeptide can form a helical secondary structure. Besides, helix directions of the C-glycosyl beta/beta(2)-peptides are governed by the configuration at the alpha-carbon of the peptide backbone that originates from the stereocenter of the C-glycosyl beta(2)-amino acids.
authors.affiliation: Department of Interdisciplinary Materials Science, Nara Women's University, Nara 630-8506, Japan.
authors.forename: Yoko
authors.initials: Y
authors.lastname: Inaba
authors.forename: Toru
authors.initials: T
authors.lastname: Kawakami
authors.forename: Saburo
authors.initials: S
authors.lastname: Aimoto
authors.forename: Takahisa
authors.initials: T
authors.lastname: Ikegami
authors.forename: Takae
authors.initials: T
authors.lastname: Takeuchi
authors.forename: Takashi
authors.initials: T
authors.lastname: Nakazawa
authors.forename: Shigenobu
authors.initials: S
authors.lastname: Yano
authors.forename: Yuji
authors.initials: Y
authors.lastname: Mikata
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D006020:Glycopeptides; D010455:Peptides