Abstract
Bioorthogonal chemistry is a set of methods using the chemistry of non-native functional groups to explore and understand biology in living organisms. In this review, we summarize the most common reactions used in bioorthogonal methods, their relative advantages and disadvantages, and their frequency of occurrence in the published literature. We also briefly discuss some of the less common but potentially useful methods. We then analyze the bioorthogonal-related publications in the CAS Content Collection to determine how often different types of biomolecules such as proteins, carbohydrates, glycans, and lipids have been studied using bioorthogonal chemistry. The most prevalent biological and chemical methods for attaching bioorthogonal functional groups to these biomolecules are elaborated. We also analyze the publication volume related to different types of bioorthogonal applications in the CAS Content Collection. The use of bioorthogonal chemistry for imaging, identifying, and characterizing biomolecules and for delivering drugs to treat disease is discussed at length. Bioorthogonal chemistry for the surface attachment of proteins and in the use of modified carbohydrates is briefly noted. Finally, we summarize the state of the art in bioorthogonal chemistry and its current limitations and promise for its future productive use in chemistry and biology.
Highlights
Bioorthogonal chemistry is a set of methods using the chemistry of non-native functional groups to explore and understand biology in living organisms
Bioorthogonal chemistry is a set of reactions that can take place in biological environments without affecting biomolecules or interfering with biochemical processes.[1−6] The term was coined by the research group of Carolyn Bertozzi[7] and likely derives from the mathematical concept of “orthogonality” used to describe two entities which vary independently of one another
Bioorthogonal chemistry allows organic synthesis ordinarily performed in a laboratory to be performed in living organisms and cells
Summary
Bioorthogonal chemistry is a set of reactions that can take place in biological environments without affecting biomolecules or interfering with biochemical processes.[1−6] The term was coined by the research group of Carolyn Bertozzi[7] and likely derives from the mathematical concept of “orthogonality” used to describe two entities which vary independently of one another. Unlike many reactions in the laboratory, bioorthogonal reactions are not intended to prepare large amounts of material. Instead, they are intended to covalently modify biomolecules with non-native functional groups under biological conditions to allow their study and manipulation. A bioorthogonal handle (such as an azide group) is incorporated into biomolecules using methods such as metabolic labeling. This review starts by providing a brief overview and comparison of established and emerging bioorthogonal reactions, followed by more detailed discussion of their actual uses, including methods for introducing bioorthogonal handles into biological systems, as well as successful applications of bioorthogonal chemistry in imaging, labeling, and drug delivery. We summarize our perceptions of the current status, limitations, and future outlook of bioorthogonal chemistry
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