title: Synthesis and characterization of chiral N-O turns induced by alpha-aminoxy acids.
abstract: Chiral alpha-aminoxy acids of various side chains were synthesized with high optical purity starting from chiral alpha-amino acids. The conformations of diamides 13a-e, 15, and 16 were probed by using NMR, FT-IR, and CD spectroscopic methods as well as X-ray crystallography. The right-handed turns with eight-membered-ring intramolecular hydrogen bonds between adjacent residues (called the N-O turns) were found to be preferred for D-aminoxy acid residues, and they were independent of the side chains. The rigid chiral N-O turns should have great potential in molecular design.
authors.affiliation: Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong. yangdan@hku.hk
authors.forename: D
authors.initials: D
authors.lastname: Yang
authors.forename: B
authors.initials: B
authors.lastname: Li
authors.forename: F F
authors.initials: FF
authors.lastname: Ng
authors.forename: Y L
authors.initials: YL
authors.lastname: Yan
authors.forename: J
authors.initials: J
authors.lastname: Qu
authors.forename: Y D
authors.initials: YD
authors.lastname: Wu
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D017433:Protein Structure, Secondary; D013057:Spectrum Analysis; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids