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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Published on: September 28, 2022

Site-Selective Reactions with Peptide-Based Catalysts.

Michael W Giuliano¹, Scott J Miller²

¹Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT, 06520-8107, USA.

Topics in Current Chemistry

|August 27, 2015

Summary

Developing peptide catalysts to control site-selectivity in chemical reactions addresses challenges posed by substrates with unequal reactivity. This research explores overcoming intrinsic substrate preferences for targeted chemical transformations.

Keywords:

Asymmetric synthesis Catalysis Natural products Peptides Site-selective reactions

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Area of Science:

Organic Chemistry
Catalysis
Supramolecular Chemistry

Background:

Achieving site-selectivity in chemical reactions is challenging, particularly when substrates possess reactive sites of differing inherent reactivity.
Overcoming these intrinsic reactivity preferences often requires catalysts capable of surmounting significant energetic barriers, exceeding those in enantioselective catalysis.

Purpose of the Study:

To present the development and application of peptide-based catalysts for achieving site-selective chemical transformations.
To investigate the relationship between substrate reactivity and catalyst design in overcoming inherent substrate preferences.

Main Methods:

Design and synthesis of peptide catalysts tailored for specific substrate recognition and activation.
Evaluation of catalyst performance in controlling site-selectivity through kinetic and mechanistic studies.
Analysis of substrate electronic and steric properties to understand inherent reactivity biases.

Main Results:

Demonstrated successful site-selective reactions using engineered peptide catalysts.
Identified key catalyst features that effectively override intrinsic substrate reactivity preferences.
Established a correlation between understanding substrate reactivity and successful catalyst development.

Conclusions:

Peptide catalysts offer a promising strategy for addressing complex site-selectivity challenges in organic synthesis.
A deep understanding of substrate reactivity is crucial for designing effective catalysts that can control reaction pathways.
This work provides a framework for developing bespoke catalysts to achieve precise chemical control over challenging substrates.