Mesogenic 4-alkoxy-2-hydroxy-4’-formylazobenzenes

Kuvshinova, S. A.; Zav’yalov, A. V.; Burmistrov, V. A.; Aleksandriiskii, V. V.; Койфман, О. И.

doi:10.1134/s1070428006030092

Cited by 4 publications

(4 citation statements)

References 1 publication

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“…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: 68%

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

Yang

Grammel

Raghavan

et al. 2010

Chemistry & Biology

114

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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: 68%

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

Yang

Grammel

Raghavan

et al. 2010

Chemistry & Biology

114

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“…(34, 35) Therefore a model reaction of the diazonium reagents with N -acyl tyrosine methylamide 4 was studied first. The reaction was performed in 67% sodium phosphate buffer/DMSO at room temperature.…”

Section: Resultsmentioning

confidence: 99%

“…32,33 The reactivity profile of 4-formyl diazonium salts has not been extensively studied; only two reports were found in the literature and these concerned reactivity with phenol. 34,35 Therefore, a model reaction of the diazonium reagents with Nacyl tyrosine methylamide 4 was studied first. The reaction was performed in 67% sodium phosphate buffer/DMSO at room temperature.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Formylbenzene Diazonium Hexafluorophosphate Reagent for Tyrosine-Selective Modification of Proteins and the Introduction of a Bioorthogonal Aldehyde

et al. 2012

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4-Formylbenzene diazonium hexafluorophosphate (FBDP) is a novel bench-stable crystalline diazonium salt that reacts selectively with tyrosine to install a bioorthogonal aldehyde functionality. Model studies with N-acyl-tyrosine methylamide allowed us to identify conditions optimal for tyrosine ligation reactions with small peptides and proteins. FBDP-based conjugation was used for the facile introduction of small molecule tags, poly(ethylene) glycol chains (PEGylation), and functional small molecules onto model proteins and to label the surface of living cells.

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“…Molecular systems based on classic (nonassociated) LCs have been thoroughly studied and are widely used in various fields of science and technology. There is now great interest in studying the properties of a new type of LC, one that contains polar terminal fragments whose molecules are able to associate and form supermolecules [4,5]. The resulting mesophases are in this case formed not by the original LC molecules but by the newly formed supermolecules.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamics of the adsorption of organic compounds from the gas phase over a monolayer of liquid crystal formed on the surface of a carbon adsorbent

Kopytin

Bykov

Onuchak

et al. 2015

Russ. J. Phys. Chem.

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Inverse gas-solid chromatography is used to study the adsorption of vapors of organic compounds with different structures and polarities on a carbon adsorbent modified with a monolayer of 4-(3-hydroxypropyloxy)-4'-formylazobenzene (HPOFAB) polar LIQUID crystal. The resulting thermodynamic characteristics of adsorption on the original and modified adsorbents are compared. The effect the nature and structure of adsorbate molecules and the liquid crystal modifier have on the thermodynamic characteristics of adsorption is considered.

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Mesogenic 4-alkoxy-2-hydroxy-4’-formylazobenzenes

Cited by 4 publications

References 1 publication

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

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

Formylbenzene Diazonium Hexafluorophosphate Reagent for Tyrosine-Selective Modification of Proteins and the Introduction of a Bioorthogonal Aldehyde

Thermodynamics of the adsorption of organic compounds from the gas phase over a monolayer of liquid crystal formed on the surface of a carbon adsorbent

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