A Biosynthetic Route to Photoclick Chemistry on Proteins

Wang, Jiangyun; Zhang, Wei; Song, Weiguo; Wang, Yizhong; Yu, Zhipeng; Li, Jiasong; Wu, Mingzai; Wang, Lin; Zang, Jianye; Lin, Qing

doi:10.1021/ja104350y

Cited by 126 publications

(101 citation statements)

References 41 publications

(34 reference statements)

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“…Their generation requires irradiation with ultraviolet light (this is termed a 'photo-click'). The reaction has been used to modify a number of alkenyl-UAAs site specifically, such as homoallylglycine 112 and cyclopropenes 113 , while the genetic incorporation of tetrazoles has also been achieved as a reactive handle for undertaking 'photo-click' reactions 114 . While the rates of reaction are now approaching levels seen for norbornene-tetrazine conjugations, the reaction is still somewhat slower than cyclooctene-tetrazine reactions.…”

Section: Review Nature Communications | Doi: 101038/ncomms5740mentioning

confidence: 99%

Selective chemical protein modification

2014

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Section: Review Nature Communications | Doi: 101038/ncomms5740mentioning

confidence: 99%

Selective chemical protein modification

2014

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“…The mixtures were irradiated with a 260 nm UV lamp (intensity, 5 mW·cm -²) for 0. 5,1,2,3,4,5,6,7,8,10 s, respectively. UV-Vis absorption spectra were recorded after irradiation.…”

Section: Kinetic Study Of Uv-induced 13-dipolar Nucleophilic Additiomentioning

confidence: 99%

UV‐Induced Tetrazole‐Thiol Reaction for Polymer Conjugation and Surface Functionalization

Feng

Yang

et al. 2015

Angew Chem Int Ed

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A UV-induced 1,3-dipolar nucleophilic addition of tetrazoles to thiols is described. Under UV irradiation the reaction proceeds rapidly at room temperature, with high yields, without a catalyst, and in both polar protic and aprotic solvents, including water. This UV-induced tetrazole-thiol reaction was successfully applied for synthesis of small molecules, protein modification, and rapid and facile polymer-polymer conjugation.The reaction has been also demonstrated for the formation of micropatterns by site-selective surface functionalization. Superhydrophobic-hydrophilic micropatterns were successfully created by sequential modifications of a tetrazole-modified porous polymer surface with hydrophobic and hydrophilic thiols. A biotin functionalized surface could be fabricated in aqueous solutions under long-wavelength UV irradiation.Ever since the first reported photoreaction of an organic compound, santonin, in 1834 by Trommsdorf, [1] the spatially and temporally controllable photochemistry has found diverse and widespread applications, [2] including surface functionalization to create patterned or gradient immobilization of various substrates.[3] Photo-induced click reactions have been actively investigated during the last decade in attempts to combine the benefits of click reactions with the excellent spatial and temporal controllability of photochemical processes.[4] UV-induced thiolene and thiol-yne reactions are the most known radical photoclick reactions.[5] Non-radical photoreactions have also attracted a lot of attention in recent years.[6] For instance, Lin et al, [7] introduced a photo-click 1,3-dipolar tetrazole-ene reaction based on Huisgen's studies. [8] The tetrazole-ene reaction presents several advantages: simplicity of implementation, fast reaction kinetics, high yields, it is catalyst free, yields inoffensive byproducts (N2) and, therefore, bio-compatible. This and other photo reactions have been implemented in many different applications such as dendrimers synthesis, [9] bioconjugation, [6b, 6d, 6e, 10] in situ bio-labeling, [6c, 11] hydrogels formation, [12] surface functionalization [13] etc. Nevertheless, the implementation of photo reactions in bio-applications is still limited, partly because unnatural functional groups have to be first introduced to a biomolecule. In addition, only a few photo reactions could be applied for polymer-polymer coupling and site-selective conjugation of biomolecules on surfaces. [13b, 14] Thus, despite a progress in the field of photo-induced reactions, there is a clear need for novel efficient photo reactions that are selective to different types of functionalities, compatible with polymerpolymer conjugation and bioapplications. 50 years ago Huisgen et al. reported that thiophenol could be added to the intermediate nitrilimine generated from decomposition of 2,5-diphenyltetrazole in boiling thiophenol. [8a, 8b] Photolytic decomposition of tetrazoles with release of nitrogen and nitrilimines was also described.[8c] In this work, we repo...

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“…To this end, we synthesized a series of tetrazole modified unnatural amino acids (Scheme 8b), and tested their reactivity in the photo-triggered cycloaddition reaction with methyl methacrylate in PBS/MeCN (1:1) [43]. While four out of six tetrazole amino acids gave excellent reaction yields, only p-tetrazole-phenylalanine (p-Tpa) was incorporated into myoglobin sitespecifically using an evolved synthetase via the amber codon suppression [44]. A drawback of this genetically encodable tetrazole amino acid is that a 254-nm UV light is needed for triggering the reaction because of the shortened π-conjugation system.…”

Section: Site-specific Labeling Of Proteins Via the Photoinduced Tetrmentioning

confidence: 99%

Photo-Triggered Click Chemistry for Biological Applications

Herner¹,

Qi²

2015

Cycloadditions in Bioorthogonal Chemistry

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In the last decade and a half, numerous bioorthogonal reactions have been developed with a goal to study biological processes in their native environment, i.e., in living cells and animals. Among them, the photo-triggered reactions offer several unique advantages including operational simplicity with the use of light rather than toxic metal catalysts and ligands, and exceptional spatiotemporal control through the application of an appropriate light source with pre-selected wavelength, light intensity and exposure time. While the photoinduced reactions have been studied extensively in materials research, e.g., on macromolecular surface, the adaptation of these reactions for chemical biology applications is still in its infancy. In this chapter, we review the recent efforts in the discovery and optimization the photo-triggered bioorthogonal reactions, with a focus on those that have shown broad utility in biological systems. We discuss in each cases the chemical and mechanistic background, the kinetics of the reactions and the biological applicability together with the limiting factors.

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A Biosynthetic Route to Photoclick Chemistry on Proteins

Cited by 126 publications

References 41 publications

Selective chemical protein modification

Selective chemical protein modification

UV‐Induced Tetrazole‐Thiol Reaction for Polymer Conjugation and Surface Functionalization

Photo-Triggered Click Chemistry for Biological Applications

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