Chemical Waltz of Organic Molecules “On Water”: Saline-Assisted Sustainable Regioselective Synthesis of Fluorogenic Heterobioconjugates via Click Reaction

Jain, Yachana; Yadav, Priya; Kumari, Mitlesh

doi:10.1021/acsomega.8b03167

Cited by 15 publications

(4 citation statements)

References 73 publications

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“…This effect is in concordance with the previous results in CuAAC, which demonstrate that this click reaction is favored by the presence of NaCl in the medium [39]. no.…”

Section: Selective Covalent Immobilization Of Azido Enzymes On Geranyl Support By Azide-cycloaddition Reactionsupporting

confidence: 93%

Geranyl Functionalized Materials for Site-Specific Co-Immobilization of Proteins

et al. 2021

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Different materials containing carboxylic groups have been functionalized with geranyl-amine molecules by using an EDC/NHS strategy. Chemical modification of the support was confirmed by XRD, UV-spectrophotometer, and FT-IR. This geranyl-functionalized material was successfully applied for four different strategies of site-selective immobilization of proteins at room temperature and aqueous media. A reversible hydrophobic immobilization of proteins (lipases, phosphoglucosidases, or tyrosinase) was performed in neutral pH in yields from 40 to >99%. An increase of the activity in the case of lipases was observed from a range of 2 to 4 times with respect to the initial activity in solution. When chemically or genetically functionalized cysteine enzymes were used, the covalent immobilization, via a selective thiol-alkene reaction, was observed in the presence of geranyl support at pH 8 in lipases in the presence of detergent (to avoid the previous hydrophobic interactions). Covalent attachment was confirmed with no release of protein after immobilization by incubation with hydrophobic molecules. In the case of a selenium-containing enzyme produced by the selenomethionine pathway, the selective immobilization was successfully yielded at acidic pH (pH 5) (89%) much better than at pH 8. In addition, when an azido-enzyme was produced by the azide–homoalanine pathway, the selective immobilization was successful at pH 6 and in the presence of CuI for the click chemistry reaction.

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“…This effect is in concordance with the previous results in CuAAC, which demonstrate that this click reaction is favored by the presence of NaCl in the medium [39]. no.…”

Section: Selective Covalent Immobilization Of Azido Enzymes On Geranyl Support By Azide-cycloaddition Reactionsupporting

confidence: 93%

Geranyl Functionalized Materials for Site-Specific Co-Immobilization of Proteins

et al. 2021

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“…Polymer science has profited from CuAAC by its simplicity, ease, scope, applicability, and efficiency. In addition, click chemistry has found wide application in drug discovery bioconjugation reactions, and polymer chemistry has pharmaceutical and biomedical applications. − Furthermore, it has greatly facilitated the overall drug discovery process by providing easy access for the synthesis of building blocks for new molecular entities. CuAAC reaction is usually carried out with organic solvents, such as dimethylformamide (DMF), toluene, or tetrahydrofuran (THF). − Traditional organic solvents could potentially cause various health and environmental concerns due to their volatility and toxicity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO₂

et al. 2021

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A new sustainable green protocol for obtaining polyethylene glycol (PEG) conjugates, with a prototype molecule, which in this work was coumarin, by means of click chemistry is presented. The organic solvents commonly used for this type of reaction were replaced by supercritical carbon dioxide (scCO2). The synthesis and characterization of PEG-coumarin were successfully reported using FTIR, 1H NMR, and MALDI TOF. Subsequently, a preliminary study was carried out using the response surface methodology to examine the variables that most affect the use of scCO2 as a reaction medium. The main effects caused by these variables, individually and their binary interaction, have been estimated. The response surface methodology has been used in this work to screen variables using a factorial design 23. The p-values of temperature and pressure were 0.006 and 0.0117, being therefore the most significant variables of the response surface methodology study. Subsequently, a more intensive study has been carried out on the variables that have shown the greatest significant effect on reaction performance where an 82.32% synthesis success was achieved, which broadens the scope of the use of scCO2 as a reaction medium. The conjugated coumarin with mPEG-alkyne and coumarin were evaluated for their in vitro antioxidant activities by the DPPH radical scavenging assay and were found to exhibit substantial activities. The click product showed comparable or even better efficacy than the initial coumarin.

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“…As part of our continuing interest in the improvement of viability and eco‐friendliness for synthesis of heterocycles, here we adopted a simple, green, efficient and scale‐up protocol for the synthesis of fluorescent coumarin based biologically significant 1,2,3‐triazoles from different terminal alkynes and coumarin azide derivatives by using CuO‐graphene oxide (CuO‐GO) nanocomposite in water under ultrasonic irradiation at 45 °C. The catalyst could be easily recovered from the reaction mixture and reused at least nine times without significant drop of %yield of the product.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound Promoted Fabrication of CuO‐Graphene Oxide Nanocomposite for Facile Synthesis of Fluorescent Coumarin Based 1,4‐disubsituted 1,2,3‐triazoles in Aqueous Media

2019

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Herein, we report a highly efficient sonochemical synthesis of CuO‐graphene oxide nanocomposite and its application as a recyclable catalyst for copper catalyzed azide‐alkyne cycloaddition (CuAAC) reaction of 3‐azidocoumarin derivatives and various terminal alkynes for the robust synthesis of regioselective fluorescent 1,4‐disubsituted triazoles (3 a‐o). This protocol includes water as a clean medium, effectively low copper loading, operational simplicity, good to excellent yield (up to 97%) in lesser time (60 min) and diverse substrate scope. Easy catalyst separation from reaction media and its recycling up to nine consecutive cycles without appreciable loss in the product yield are other noteworthy features of this protocol. The optimized reaction conditions were then explored successfully to get 90% yield at gram scale level.

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Chemical Waltz of Organic Molecules “On Water”: Saline-Assisted Sustainable Regioselective Synthesis of Fluorogenic Heterobioconjugates via Click Reaction

Cited by 15 publications

References 73 publications

Geranyl Functionalized Materials for Site-Specific Co-Immobilization of Proteins

Geranyl Functionalized Materials for Site-Specific Co-Immobilization of Proteins

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO₂

Ultrasound Promoted Fabrication of CuO‐Graphene Oxide Nanocomposite for Facile Synthesis of Fluorescent Coumarin Based 1,4‐disubsituted 1,2,3‐triazoles in Aqueous Media

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Chemical Waltz of Organic Molecules “On Water”: Saline-Assisted Sustainable Regioselective Synthesis of Fluorogenic Heterobioconjugates via Click Reaction

Cited by 15 publications

References 73 publications

Geranyl Functionalized Materials for Site-Specific Co-Immobilization of Proteins

Geranyl Functionalized Materials for Site-Specific Co-Immobilization of Proteins

Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO2

Ultrasound Promoted Fabrication of CuO‐Graphene Oxide Nanocomposite for Facile Synthesis of Fluorescent Coumarin Based 1,4‐disubsituted 1,2,3‐triazoles in Aqueous Media

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Synthesis and Operating Optimization of the PEG Conjugate via CuAAC in scCO₂