Optimization of the Azobenzene Scaffold for Reductive Cleavage by Dithionite; Development of an Azobenzene Cleavable Linker for Proteomic Applications

Leriche, Geoffray; Budin, Ghyslain; Brino, Laurent; Wagner, Alain

doi:10.1002/ejoc.201000546

Cited by 47 publications

(27 citation statements)

References 25 publications

(12 reference statements)

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“…Strong electron-donating group, like -OH on ortho position accelerates the Na 2 S 2 O 4 -cleavage, while the presence of weak electron-withdrawing group, like bromine on ortho position slightly impedes this cleavage efficiency. These results are consistent with recent structure-reactivity studies of diazobenzene derivatives by Wagner and coworkers (Leriche et al, 2010). Nevertheless, it is worth to mention that ortho -hydroxyl group may not impose its effect on diazobenzene-bond reactivity toward Na 2 S 2 O 4 merely through mesomeric effect.…”

Section: Discussionsupporting

confidence: 93%

“…Nevertheless, it is worth to mention that ortho -hydroxyl group may not impose its effect on diazobenzene-bond reactivity toward Na 2 S 2 O 4 merely through mesomeric effect. As indicated in our studies and Wagner and coworkers (Leriche et al, 2010), para -alkoxylated diazobenzne ( 3 and 4 in this study) did not possess better cleavage efficiencies, suggesting ortho -hydroxyl group might accelerate the diazobenzene-bond cleavage through other mechanisms such as intramolecular hydrogen bonding with nitrogen atom of diazobenzene (Kuvshinova et al, 2006). Further detailed investigation on Na 2 S 2 O 4 -mediated diazobenzene cleavage mechanism and structure-and-activity studies would help to reveal the roles of ortho -hydroxyl group in this reaction.…”

Section: Discussionsupporting

confidence: 72%

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Comparative Analysis of Cleavable Azobenzene-Based Affinity Tags for Bioorthogonal Chemical Proteomics

Yang

Grammel

Raghavan

et al. 2010

Chemistry & Biology

113

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SUMMARY The advances in bioorthogonal ligation methods have provided new opportunities for proteomic analysis of newly synthesized proteins, posttranslational modifications and specific enzyme families using azide/alkyne-functionalized chemical reporters and activity-based probes. Efficient enrichment and elution of azide/alkyne-labeled proteins with selectively cleavable affinity tags is essential for protein identification and quantification applications. Here we report the synthesis and comparative analysis of Na2S2O4-cleavable diazobenzene-based affinity tags for bioorthogonal chemical proteomics. We demonstrated that ortho-hydroxyl substituent is required for efficient diazobenzene-bond cleavage and show that these cleavable affinity tags can be used to identify newly synthesized proteins in bacteria targeted by amino acid chemical reporters as well as their sites of modification on endogenously expressed proteins. The diazobenzene-based affinity tags are compatible with in-gel, in-solution and on-bead enrichment strategies and should afford useful tools for diverse bioorthogonal proteomic applications.

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Section: Discussionsupporting

confidence: 93%

Section: Discussionsupporting

confidence: 72%

Comparative Analysis of Cleavable Azobenzene-Based Affinity Tags for Bioorthogonal Chemical Proteomics

Yang

Grammel

Raghavan

et al. 2010

Chemistry & Biology

113

View full text Add to dashboard Cite

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“…The organic phase was dried with MgSO 4 , filtered, and evaporated. The crude product was purified by 31 In a 100 mL round-bottom flask equipped with …”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Are Two Azo Groups Better than One? Investigating the Photoresponse of Polymer-Bisazobenzene Complexes

et al. 2014

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Azobenzene chromophores are an ideal choice for material applications where functionality needs to be activated in a precise remote-controlled fashion. The azobenzene stimuli-response falls into two categories, either based on efficient trans-to-cis photoisomerization and a high cis yield enabling on−off type functions, or relying on a fast trans−cis−trans cycling creating motion in the material system. Herein, we show that using bisazochromophores instead of the more common monoazobenzene derivatives makes a difference in the performance of light-responsive azopolymers, more specifically in photo-orientation and all-optical surface patterning. Our findings point out that polymer-bisazobenzene complexes are an attractive alternative as high-performance photoreponsive materials and that although their properties are highly sensitive to the extent of conjugation in the system, they can be designed into relatively transparent films with high performance for all-optical patterning.

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“…The synthesis was based on that of the whole cis ‐diol‐linked alkyne building block 1 and its direct aqueous Sonogashira cross‐coupling with dC I TP (in analogy to a procedure previously developed in our laboratory). The known N ‐hydroxysuccinimide (NHS)‐ester of hex‐5‐ynoic acid ( 3 ) was used for the acylation of 3‐pyrroline in dichloromethane to produce amide 2 , which was then cis ‐dihydroxylated with a catalytic amount of K 2 OsO 4 and N ‐methylmorpholine‐ N ‐oxide to give the cis ‐diol alkyne 1 . Then, this alkyne was linked to known 5‐iodo‐2′‐deoxycytidine 5′‐ O ‐triphosphate ( dC I TP ) through an aqueous Sonogashira cross‐coupling reaction in the presence of Pd(OAc) 2 , TPPTS, CuI, and triethylamine to obtain the desired modified nucleoside triphosphate dC PDI TP in a good yield of 59 %.…”

Section: Resultsmentioning

confidence: 99%

Vicinal Diol‐Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes

et al. 2019

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Six‐valent osmium (osmate) complexes with nitrogenous ligands have previously been used for the modification and redox labeling of biomolecules involving vicinal diol moieties (typically, saccharides or RNA). In this work, aliphatic (3,4‐dihydroxybutyl and 3,4‐dihydroxybut‐1‐ynyl) or cyclic (6‐oxo‐6‐(cis‐3,4‐dihydroxypyrrolidin‐1‐yl)hex‐2‐yn‐1‐yl, PDI) vicinal diols are attached to nucleobases to functionalize DNA for subsequent redox labeling with osmium(VI) complexes. The diol‐linked 2′‐deoxyribonucleoside triphosphates were used for the polymerase synthesis of diol‐linked DNA, which, upon treatment with K2OsO3 and bidentate nitrogen ligands, gave the desired Os‐labeled DNA, which were characterized by means of the gel‐shift assay and ESI‐MS. Through ex situ square‐wave voltammetry at a basal plane pyrolytic graphite electrode, the efficiency of modification/labeling of individual diols was evaluated. The results show that the cyclic cis‐diol (PDI) was a better target for osmylation than that of the flexible aliphatic ones (alkyl‐ or alkynyl‐linked). The osmate adduct‐specific voltammetric signal obtained for OsVI‐treated DNA decorated with PDI showed good proportionality to the number of PDI per DNA molecule. The OsVI reagents (unlike OsO4) do not attack nucleobases; thus offering specificity of modification on the introduced glycol targets.

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Optimization of the Azobenzene Scaffold for Reductive Cleavage by Dithionite; Development of an Azobenzene Cleavable Linker for Proteomic Applications

Cited by 47 publications

References 25 publications

Comparative Analysis of Cleavable Azobenzene-Based Affinity Tags for Bioorthogonal Chemical Proteomics

Comparative Analysis of Cleavable Azobenzene-Based Affinity Tags for Bioorthogonal Chemical Proteomics

Are Two Azo Groups Better than One? Investigating the Photoresponse of Polymer-Bisazobenzene Complexes

Vicinal Diol‐Tethered Nucleobases as Targets for DNA Redox Labeling with Osmate Complexes

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