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One-bead-one-catalyst approach to aspartic acid-based oxidation catalyst discovery
Phillip A Lichtor1, Scott J Miller
1Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, United States.
ACS Combinatorial Science
|March 23, 2011
Summary
We developed a high-throughput screening method for asymmetric oxidation catalysts using a one-bead-one-compound library. This peptide-based approach efficiently identifies novel catalysts for enantioselective oxidation reactions.
Area of Science:
- Organic Chemistry
- Catalysis
- Chemical Biology
Background:
- Asymmetric oxidation reactions are crucial in synthesizing chiral molecules.
- Developing efficient and high-throughput methods for catalyst discovery is essential.
Purpose of the Study:
- To establish a high-throughput screening (HTS) approach for asymmetric oxidation catalysts.
- To utilize a one-bead-one-compound (OBOC) library strategy based on peptide scaffolds.
Main Methods:
- Employed a recently developed catalytic cycle featuring an acid-peracid shuttle.
- Developed a compatible linker for the OBOC library.
- Utilized partial Edman degradation and MALDI mass spectrometry for catalyst sequencing.
Main Results:
- Demonstrated the library format's suitability for screening and sequencing peptide-based catalysts.
- Successfully applied the system to discover and rediscover catalysts for enantioselective oxidation of a cyclohexene derivative.
Conclusions:
- The developed HTS approach is effective for identifying asymmetric oxidation catalysts.
- The system is adaptable for discovering catalysts for new substrate classes and asymmetric oxidation reactions.
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