title: New preorganized γ-amino acids as foldamer building blocks.
abstract: An asymmetric synthesis of two new diastereomeric γ-amino acids is described. Both molecules contain a cyclohexyl ring to limit conformational flexibility about the Cα-Cβ bond; they differ in having cis vs trans stereochemistry on the ring. Residues derived from the cis γ isomer are shown to support helical secondary structures in α/γ-peptide oligomers.
authors.affiliation: Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53706, United States.
authors.forename: Li
authors.initials: L
authors.lastname: Guo
authors.forename: Weicheng
authors.initials: W
authors.lastname: Zhang
authors.forename: Ilia A
authors.initials: IA
authors.lastname: Guzei
authors.forename: Lara C
authors.initials: LC
authors.lastname: Spencer
authors.forename: Samuel H
authors.initials: SH
authors.lastname: Gellman
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D053138:Cyclohexenes / Q000737:chemistry*; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry; D017433:Protein Structure, Secondary; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D053138:Cyclohexenes; D010455:Peptides; C052568:cyclohexene