title: Stereoselective recognition of tripeptides guided by encoded library screening: construction of chiral macrocyclic tetraamide ruthenium receptor for peptide sensing.
abstract: [structure: see text] Molecule sensor 1 is devised by incorporating the reporting unit of ruthenium(II) complex and two recognition motifs of chiral cyclotetraamides on the sidearms. The target binding tripeptides for sensor 1 were readily identified by using an encoded library screening method. This solid-phase screening indicated a preferable binding of molecule 1 with d-alanine over the l-isomer. The optical and NMR studies for the binding events of 1 with tripeptides Ac-Ala-Gly-Ala-NHC(12)H(25) in the solution phase showed a consistent trend for the stereoselective recognition of the dd-isomer over the ld-, dl-, and ll-isomers.
authors.affiliation: Department of Chemistry, National Taiwan University, Taipei 106, Taiwan.
authors.forename: Kuei-Hua
authors.initials: KH
authors.lastname: Chang
authors.forename: Jen-Hai
authors.initials: JH
authors.lastname: Liao
authors.forename: Chao-Tsen
authors.initials: CT
authors.lastname: Chen
authors.forename: Barun K
authors.initials: BK
authors.lastname: Mehta
authors.forename: Pi-Tai
authors.initials: PT
authors.lastname: Chou
authors.forename: Jim-Min
authors.initials: JM
authors.lastname: Fang
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D046911:Macromolecular Substances; D008968:Molecular Conformation; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis*; D019151:Peptide Library; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D046911:Macromolecular Substances; D009842:Oligopeptides; D009942:Organometallic Compounds; D019151:Peptide Library; D012428:Ruthenium