Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms

Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller

doi:10.1021/acs.chemrev.0c00523

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Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms

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Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms

Anthony J Metrano, Alex J Chinn, Christopher R Shugrue, Elizabeth A Stone, Byoungmoo Kim and Scott J Miller

Chemical reviews, Vol.120(20), pp.11479-11615

10/28/2020

DOI: 10.1021/acs.chemrev.0c00523

PMCID: PMC8006536

PMID: 32969640

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https://www.ncbi.nlm.nih.gov/pmc/articles/8006536View

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Abstract

Low molecular weight synthetic peptides have been demonstrated to be effective catalysts for an increasingly wide array of asymmetric transformations. In many cases, these peptide-based catalysts have enabled novel multifunctional substrate activation modes and unprecedented selectivity manifolds. These features, along with their ease of preparation, modular and tunable structures, and often biomimetic attributes make peptides well-suited as chiral catalysts and of broad interest. Many examples of peptide-catalyzed asymmetric reactions have appeared in the literature since the last survey of this broad field in Chemical Reviews (Chem. Rev. 2007, 107, 5759–5812). The overarching goal of this new Review is to provide a comprehensive account of the numerous advances in the field. As a corollary to this goal, we survey the many different types of catalytic reactions, ranging from acylation to C–C bond formation, in which peptides have been successfully employed. In so doing, we devote significant discussion to the structural and mechanistic aspects of these reactions that are perhaps specific to peptide-based catalysts and their interactions with substrates and/or reagents.

Details

Title: Subtitle: Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms
Creators: Anthony J Metrano - AstraZeneca Oncology R&D
Alex J Chinn - Princeton University
Christopher R Shugrue - Department of Chemistry
Elizabeth A Stone - Department of Chemistry
Byoungmoo Kim - Department of Chemistry
Scott J Miller - Department of Chemistry
Resource Type: Journal article
Publication Details: Chemical reviews, Vol.120(20), pp.11479-11615
DOI: 10.1021/acs.chemrev.0c00523
PMID: 32969640
PMCID: PMC8006536
NLM abbreviation: Chem Rev
ISSN: 0009-2665
eISSN: 1520-6890
Publisher: American Chemical Society
Grant note: DOI: 10.13039/100000057, name: National Institute of General Medical Sciences, award: F32-GM128245, F32-GM13307301, R35 GM132092; DOI: 10.13039/100000001, name: National Science Foundation
Language: English
Date published: 10/28/2020
Academic Unit: Chemistry; Chemical and Biochemical Engineering
Record Identifier: 9984217433002771

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