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Discovery of selective metal-binding peptoids using 19F encoded combinatorial libraries
1Department of Chemistry, Levine Science Research Center, Duke University, Durham, NC 27708-0317, USA. pirrung@chem.duke.edu
Bioorganic & Medicinal Chemistry Letters
|September 22, 2000
Summary
Researchers developed a novel method using fluorinated aromatic compounds (F-codes) for encoding chemical libraries synthesized on solid phase. This technique enables efficient decoding using 19F NMR, identifying specific metal binders.
Area of Science:
- Synthetic Chemistry
- Analytical Chemistry
- Chemical Biology
Background:
- Solid-phase synthesis is crucial for combinatorial library generation.
- Efficient encoding and decoding methods are needed for complex libraries.
- Fluorinated compounds offer unique spectroscopic properties for detection.
Purpose of the Study:
- To develop a novel encoding strategy for solid-phase combinatorial libraries.
- To utilize synthetic fluoroarenes ('F-codes') for library encoding and 19F NMR for decoding.
- To identify specific metal binders using this new methodology.
Main Methods:
- Preparation of nine fluoroarenes with photocleavable linkers for solid-phase support attachment.
- Synthesis of a 90-compound library of N-alkylglycines via split-and-mix solid-phase synthesis.
- Encoding amines with fluorinated tags and coupling with 10 anhydrides.
- Metal binding studies followed by 19F NMR decoding.
Main Results:
- Successful preparation of fluoroarene building blocks and the combinatorial library.
- Demonstrated sub-micromolar detectability of F-codes using 19F NMR.
- Identification of unique, specific binders for copper(II) and iron(III) with microM K(D)s.
Conclusions:
- The F-code method provides a robust and sensitive approach for encoding solid-phase libraries.
- 19F NMR is an effective tool for decoding these libraries.
- This method facilitates the discovery of specific metal-binding compounds.