期刊
CHEMICAL REVIEWS
卷 121, 期 12, 页码 6850-6914出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.chemrev.0c01013
关键词
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资金
- National Science Foundation [2004010]
- University of Utah Skaggs Graduate Fellowship
- American Foundation for Pharmaceutical Education PreDoctoral Fellowship
This article reviews the mechanisms and substituent effects of some of the principal metal-free bioorthogonal reactions, based on inverse-electron demand Diels-Alder reactions, 1,3-dipolar cycloadditions, and the Staudinger reaction. Modified versions that link these reactions to a dissociative step are further discussed, with the aim to aid the advancement of bioorthogonal chemistry.
Reactions that occur under physiological conditions find diverse uses in the chemical and biological sciences. However, the limitations that biological systems place on chemical reactions restrict the number of such bioorthogonal reactions. A profound understanding of the mechanistic principles and structure-reactivity trends of these transformations is therefore critical to access new and improved versions of bioorthogonal chemistry. The present article reviews the mechanisms and substituent effects of some of the principal metal-free bioorthogonal reactions based on inverse-electron demand Diels-Alder reactions, 1,3-dipolar cycloadditions, and the Staudinger reaction. Mechanisms of modified versions that link these reactions to a dissociative step are further discussed. The presented summary is anticipated to aid the advancement of bioorthogonal chemistry.
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