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Enzymatic functionalization of carbon-hydrogen bonds

Lewis, Jared C. and Coelho, Pedro S. and Arnold, Frances H. (2011) Enzymatic functionalization of carbon-hydrogen bonds. Chemical Society Reviews, 40 (4). pp. 2003-2021. ISSN 0306-0012. PMCID PMC3064445. https://resolver.caltech.edu/CaltechAUTHORS:20110414-084904112

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Abstract

The development of new catalytic methods to functionalize carbon–hydrogen (C–H) bonds continues to progress at a rapid pace due to the significant economic and environmental benefits of these transformations over traditional synthetic methods. In nature, enzymes catalyze regio- and stereoselective C–H bond functionalization using transformations ranging from hydroxylation to hydroalkylation under ambient reaction conditions. The efficiency of these enzymes relative to analogous chemical processes has led to their increased use as biocatalysts in preparative and industrial applications. Furthermore, unlike small molecule catalysts, enzymes can be systematically optimized via directed evolution for a particular application and can be expressed in vivo to augment the biosynthetic capability of living organisms. While a variety of technical challenges must still be overcome for practical application of many enzymes for C–H bond functionalization, continued research on natural enzymes and on novel artificial metalloenzymes will lead to improved synthetic processes for efficient synthesis of complex molecules. In this critical review, we discuss the most prevalent mechanistic strategies used by enzymes to functionalize non-acidic C–H bonds, the application and evolution of these enzymes for chemical synthesis, and a number of potential biosynthetic capabilities uniquely enabled by these powerful catalysts (110 references).


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1039/c0cs00067a DOIArticle
http://pubs.rsc.org/en/Content/ArticleLanding/2011/CS/c0cs00067aPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3064445/PubMed CentralArticle
ORCID:
AuthorORCID
Arnold, Frances H.0000-0002-4027-364X
Additional Information:© 2011 The Royal Society of Chemistry. Received 6th August 2010. Part of a themed issue on C–H functionalization in organic synthesis dedicated to the memory of Keith Fagnou. Prof. Keith Fagnou’s work in the field of C–H bond functionalization and on direct arylation in particular provided many exciting insights into mechanistic aspects of C–H activation chemistry and led to the development of a number of conceptually novel transformations. His constant advances inspired me to work faster and think harder. He will be missed—JCL. JCL is supported by a U.S. National Institutes of Health Pathways to Independence Award (1K99GM087551-01A1). This work was supported by the U.S. National Institutes of Health (2R01GM068664-05A1) and by the U.S. Department of Energy, Office of Basic Science, grant DE-FG02-06ER15762.
Funders:
Funding AgencyGrant Number
NIH1K99GM087551-01A1
NIH2R01GM068664-05A1
Department of Energy (DOE)DE-FG02-06ER15762
Issue or Number:4
PubMed Central ID:PMC3064445
Record Number:CaltechAUTHORS:20110414-084904112
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20110414-084904112
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:23314
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:23 Jun 2011 22:07
Last Modified:03 Oct 2019 02:45

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