☆ 4.7 Article

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

DALTON TRANSACTIONS (2023)

Related references

Note: Only part of the references are listed.

Article Chemistry, Multidisciplinary

Triazinium Ligation: Bioorthogonal Reaction of N1-Alkyl 1,2,4-Triazinium Salts

Veronika Slachtova et al.

Summary: The development of reagents selective in complex biological media is a significant challenge. We demonstrate that N1-alkylation of 1,2,4-triazines produces more reactive triazinium salts when reacting with strained alkynes compared to the parent 1,2,4-triazines. These salts facilitate efficient modification of peptides and proteins through a powerful bioorthogonal ligation. The positively charged N1-alkyl triazinium salts possess favorable cell permeability and outperform analogous 1,2,4,5-tetrazines for intracellular fluorescent labeling applications. These new ionic heterodienes exhibit high reactivity, stability, synthetic accessibility, and improved water solubility, making them valuable additions to the repertoire of modern bioorthogonal reagents.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Affinity Bioorthogonal Chemistry (ABC) Tags for Site-Selective Conjugation, On-Resin Protein-Protein Coupling, and Purification of Protein Conjugates

Samuel L. Scinto et al.

Summary: This study demonstrates a new method for site-selective functionalization of proteins using pyridyl-tetrazine tags, allowing for direct affinity purification on commonly used nickel-iminodiacetate (Ni-IDA) resins. The method is also applicable for protein purification from complex mixtures.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Add to Collection

Review Biochemical Research Methods

Bioorthogonal Chemistry and Its Applications

Robert E. Bird et al.

Summary: Bioorthogonal chemistry is a method using non-native functional groups to explore biology in living organisms. This review summarizes common reactions in bioorthogonal methods and the frequency of bioorthogonal applications on different types of biomolecules. The application of bioorthogonal chemistry in imaging, drug delivery, and protein surface attachment is discussed, highlighting its current limitations and potential for future productive use.

BIOCONJUGATE CHEMISTRY (2021)

Add to Collection

Review Chemistry, Multidisciplinary

Triazines: Syntheses and Inverse Electron-demand Diels-Alder Reactions

Fa-Guang Zhang et al.

Summary: This review highlights the importance and applications of triazines, a class of six-membered aromatic heterocycles, in the synthesis of N heterocycles, natural product preparation, and bioorthogonal chemistry. It discusses the construction of triazines through annulation and ring-expansion reactions, emphasizing their role in IEDDA cycloaddition reactions for accessing a wide scope of heterocycles. Furthermore, it explores the bioorthogonal application of triazines in fast click ligation with strained alkenes and alkynes, providing a new opportunity for studying biomolecules in chemical biology.

CHEMICAL REVIEWS (2021)

Add to Collection

Article Chemistry, Inorganic & Nuclear

[(η6-p-Cymene)[3-(pyrid-2-yl)-1,2,4,5-tetrazine]chlororuthenium(II)]+, Redox Noninnocence and Dienophile Addition to Coordinated Tetrazine

Marc Schnierle et al.

Summary: The bidentate ligand TzPy showed noninnocent behavior and could be modified by dienophiles. The kinetic analysis of the reaction between [1](+) and ViFc yielded Delta G double dagger(298 K) = 67 kJ mol(-1), while that of [1](+) and EthFc was Delta G double dagger(298 K) = 83 kJ mol(-1). The electrochemical reduction mechanism of [1Fc](+) was studied using cyclic voltammetry and UV-vis SEC experiments, supported by DFT calculations.

INORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Origin of Increased Reactivity in Rhenium-Mediated Cycloadditions of Tetrazines

Aneta Turlik et al.

Summary: Pyridyl tetrazines coordinated to metals such as rhenium exhibit higher reactivity in [4 + 2] cycloadditions compared to their uncomplexed counterparts, as a result of stronger orbital interactions. The increased regioselectivity can be attributed to a greater degree of charge stabilization in the transition state, leading to the formation of the major product.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Multidisciplinary

Tetrazine metallation boosts rate and regioselectivity of inverse electron demand Diels-Alder (iEDDA) addition of dienophiles

Marc Schnierle et al.

CHEMICAL COMMUNICATIONS (2020)

Add to Collection

Article Chemistry, Multidisciplinary

Iridium(iii) complexes of 1,2,4-triazines as potential bioorthogonal reagents: metal coordination facilitates luminogenic reaction with strained cyclooctynes

Valery N. Kozhevnikov et al.

CHEMICAL COMMUNICATIONS (2019)

Add to Collection

Article Chemistry, Multidisciplinary

Metal-Free Synthetic Approach to 3-Monosubstituted Unsymmetrical 1,2,4,5-Tetrazines Useful for Bioorthogonal Reactions

Yangyang Qu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

Add to Collection

Review Chemistry, Multidisciplinary

Inverse electron demand Diels-Alder reactions in chemical biology

B. L. Oliveira et al.

CHEMICAL SOCIETY REVIEWS (2017)

Add to Collection

Article Chemistry, Multidisciplinary

Monochromophoric iridium(III) pyridyl-tetrazine complexes as a unique design strategy for bioorthogonal probes with luminogenic behavior

Tommy Siu-Ming Tang et al.

CHEMICAL COMMUNICATIONS (2017)

Add to Collection

Article Chemistry, Multidisciplinary

1,2,4-Triazines Are Versatile Bioorthogonal Reagents

David N. Kamber et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Click to Release: Instantaneous Doxorubicin Elimination upon Tetrazine Ligation

Ron M. Versteegen et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Add to Collection

Article Biochemical Research Methods

Synthesis and Evaluation of a Series of 1,2,4,5-Tetrazines for Bioorthogonal Conjugation

Mark R. Karver et al.

BIOCONJUGATE CHEMISTRY (2011)

Add to Collection

Article Multidisciplinary Sciences

Cell surface engineering by a modified Staudinger reaction

E Saxon et al.

SCIENCE (2000)

Add to Collection

© Peeref 2019-2024. All rights reserved.