Stereoselective Recognition of Tripeptides Guided by Encoded Library Screening: Construction of Chiral Macrocyclic Tetraamide Ruthenium Receptor for Peptide Sensing
- 10 February 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (6) , 2026-2032
- https://doi.org/10.1021/jo048368s
Abstract
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-NHC12H25 in the solution phase showed a consistent trend for the stereoselective recognition of the dd-isomer over the ld-, dl-, and ll-isomers.Keywords
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