Stereoselective Recognition of Tripeptides Guided by Encoded Library Screening: Construction of Chiral Macrocyclic Tetraamide Ruthenium Receptor for Peptide Sensing | Zendy

Kuei-Hua Chang | Zendy; JenHai Liao | Zendy; ChaoTsen Chen | Zendy; Barun K. Mehta | Zendy; PiTai Chou | Zendy; JimMin Fang | Zendy

Open Access

Stereoselective Recognition of Tripeptides Guided by Encoded Library Screening: Construction of Chiral Macrocyclic Tetraamide Ruthenium Receptor for Peptide Sensing

Author(s) -

Kuei-Hua Chang,

JenHai Liao,

ChaoTsen Chen,

Barun K. Mehta,

PiTai Chou,

JimMin Fang

Publication year - 2005

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo048368s

Subject(s) - tripeptide , ruthenium , chemistry , stereochemistry , molecule , stereoselectivity , peptide , molecular recognition , combinatorial chemistry , alanine , stereoisomerism , biochemistry , amino acid , organic chemistry , catalysis

[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.

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