Stereoselective recognition of tripeptides guided by encoded library screening: construction of chiral macrocyclic tetraamide ruthenium receptor for peptide sensing.
[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.
Chang
Kuei-Hua
KH
Department of Chemistry, National Taiwan University, Taipei 106, Taiwan.
Liao
Jen-Hai
JH
Chen
Chao-Tsen
CT
Mehta
Barun K
BK
Chou
Pi-Tai
PT
Fang
Jim-Min
JM
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
D000577:Amides; D046911:Macromolecular Substances; D009842:Oligopeptides; D009942:Organometallic Compounds; D019151:Peptide Library; D012428:Ruthenium