Advances in the Synthesis of Bioorthogonal Reagents: s-Tetrazines, 1,2,4-Triazines, Cyclooctynes, Heterocycloheptynes, and trans-Cyclooctenes.


Journal

Topics in current chemistry (Cham)
ISSN: 2364-8961
Titre abrégé: Top Curr Chem (Cham)
Pays: Switzerland
ID NLM: 101691301

Informations de publication

Date de publication:
04 May 2024
Historique:
received: 30 09 2023
accepted: 01 02 2024
medline: 5 5 2024
pubmed: 5 5 2024
entrez: 4 5 2024
Statut: epublish

Résumé

Aligned with the increasing importance of bioorthogonal chemistry has been an increasing demand for more potent, affordable, multifunctional, and programmable bioorthogonal reagents. More advanced synthetic chemistry techniques, including transition-metal-catalyzed cross-coupling reactions, C-H activation, photoinduced chemistry, and continuous flow chemistry, have been employed in synthesizing novel bioorthogonal reagents for universal purposes. We discuss herein recent developments regarding the synthesis of popular bioorthogonal reagents, with a focus on s-tetrazines, 1,2,4-triazines, trans-cyclooctenes, cyclooctynes, hetero-cycloheptynes, and -trans-cycloheptenes. This review aims to summarize and discuss the most representative synthetic approaches of these reagents and their derivatives that are useful in bioorthogonal chemistry. The preparation of these molecules and their derivatives utilizes both classical approaches as well as the latest organic chemistry methodologies.

Identifiants

pubmed: 38703255
doi: 10.1007/s41061-024-00455-y
pii: 10.1007/s41061-024-00455-y
doi:

Substances chimiques

Triazines 0
Cyclooctanes 0
1,2,4-triazine 290-38-0
Alkynes 0
Indicators and Reagents 0

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

IM

Pagination

15

Subventions

Organisme : Foundation for the National Institutes of Health
ID : R01GM132460
Organisme : National Science Foundation
ID : DMR-2011824

Informations de copyright

© 2024. The Author(s), under exclusive licence to Springer Nature Switzerland AG.

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Auteurs

Yinzhi Fang (Y)

Department of Chemistry and Biochemistry, University of Delaware, 590 Avenue 1743, Newark, DE, 19713, USA. yinzhif@udel.edu.

Ashlyn S Hillman (AS)

Department of Chemistry and Biochemistry, University of Delaware, 590 Avenue 1743, Newark, DE, 19713, USA.

Joseph M Fox (JM)

Department of Chemistry and Biochemistry, University of Delaware, 590 Avenue 1743, Newark, DE, 19713, USA. jmfox@udel.edu.

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