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生物正交试剂合成的进展:s-四嗪、1,2,4-三嗪、环辛炔、杂环庚炔和反式环辛烯。

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

机构信息

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

出版信息

Top Curr Chem (Cham). 2024 May 4;382(2):15. doi: 10.1007/s41061-024-00455-y.

DOI:10.1007/s41061-024-00455-y
PMID:38703255
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11559631/
Abstract

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.

摘要

与生物正交化学的重要性不断提高相一致的是,人们对更有效、更经济、多功能和可编程的生物正交试剂的需求不断增加。更先进的合成化学技术,包括过渡金属催化交叉偶联反应、C-H 活化、光诱导化学和连续流动化学,已被用于合成用于通用目的的新型生物正交试剂。本文讨论了关于流行的生物正交试剂的合成的最新进展,重点是 s-四嗪、1,2,4-三嗪、反式环辛烯、环辛炔、杂环庚炔和 -反式环庚烯。本综述旨在总结和讨论这些试剂及其在生物正交化学中有用的衍生物的最具代表性的合成方法。这些分子及其衍生物的制备既利用了经典方法,也利用了最新的有机化学方法。

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本文引用的文献

1
Catching up with tetrazines: coordination of Re(I) to 1,2,4-triazine facilitates an inverse electron demand Diels-Alder reaction with strained alkynes to a greater extent than in corresponding 1,2,4,5-tetrazines.追赶上四嗪:铼(I)与1,2,4-三嗪的配位比在相应的1,2,4,5-四嗪中更能促进与张力炔烃的逆电子需求狄尔斯-阿尔德反应。
Dalton Trans. 2023 Aug 8;52(31):10927-10932. doi: 10.1039/d3dt01451g.
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Triazinium Ligation: Bioorthogonal Reaction of N1-Alkyl 1,2,4-Triazinium Salts.三嗪鎓连接:N1-烷基-1,2,4-三嗪鎓盐的生物正交反应
Angew Chem Int Ed Engl. 2023 Sep 4;62(36):e202306828. doi: 10.1002/anie.202306828. Epub 2023 Jul 24.
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A Concise Synthetic Approach to Highly Reactive Click-to-Release Trans-Cyclooctene Linkers.一种简洁的高反应性点击释放反式环辛烯连接子的合成方法。
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Ligand-Directed Photocatalysts and Far-Red Light Enable Catalytic Bioorthogonal Uncaging inside Live Cells.配体导向的光催化剂和远红光使活细胞内的催化生物正交解笼成为可能。
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Synthesis of Functionalized Dibenzoazacyclooctynes by a Decomplexation Method for Dibenzo-Fused Cyclooctyne-Cobalt Complexes.通过二苯并稠合环辛炔-钴配合物的解络合方法合成功能化二苯并氮杂环辛炔
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Alkali halides as nucleophilic reagent sources for N-directed palladium-catalysed -C-H halogenation of -tetrazines and other heteroaromatics.碱金属卤化物作为亲核试剂源用于氮导向钯催化的四嗪及其他杂芳烃的碳氢键卤化反应。
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Oxidative Desymmetrization Enables the Concise Synthesis of a trans-Cyclooctene Linker for Bioorthogonal Bond Cleavage.氧化去对称化实现了用于生物正交键裂解的反式环辛烯连接子的简洁合成。
Chemistry. 2023 Jan 12;29(3):e202203069. doi: 10.1002/chem.202203069. Epub 2022 Nov 24.
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Catalytic Activation of Bioorthogonal Chemistry with Light (CABL) Enables Rapid, Spatiotemporally Controlled Labeling and No-Wash, Subcellular 3D-Patterning in Live Cells Using Long Wavelength Light.用光催化生物正交化学(CABL)实现了快速、时空可控的标记,并且无需洗涤,使用长波长光对活细胞进行亚细胞 3D 图案化。
J Am Chem Soc. 2022 Feb 2;144(4):1647-1662. doi: 10.1021/jacs.1c10390. Epub 2022 Jan 24.
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Triazines: Syntheses and Inverse Electron-demand Diels-Alder Reactions.三嗪:合成与逆电子需求的狄尔斯-阿尔德反应
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Cross-Coupling Reactions of Monosubstituted Tetrazines.单取代四嗪的交叉偶联反应
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