scholarly journals Facile discovery of isonitrile natural products via tetrazine based click reactions

2019 ◽  
Author(s):  
Yaobing Huang ◽  
Wenlong Cai ◽  
Antonio Del Rio Flores ◽  
Frederick Twigg ◽  
Wenjun Zhang
Keyword(s):  
Natural Products ◽  
Click Reaction ◽  
In Situ Reduction ◽  
Click Reactions ◽  
Microbial Cultures ◽  
First Time

A facile method for the quick discovery and quantification of isonitrile compounds from microbial cultures was established based on the isonitrile-tetrazine click reaction. A in situ reduction further enabled bioorthogonal ligation of primary and secondary isonitriles for the first time.

scholarly journals SYNTHESIS OF AN AZIDE–THIOL LINKER FOR HETEROGENEOUS POLYMER FUNCTIONALIZATION VIA THE “CLICK” REACTION

2018 ◽  
Vol 55 (1B) ◽  
pp. 152
Author(s):  
Thuy Thu Truong
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Click Reaction ◽  
Proton Nuclear Magnetic Resonance ◽  
Reaction Yield ◽  
Reaction Conditions ◽  
Click Reactions ◽  
Heterogeneous Polymer ◽  
Ft Ir ◽  
First Time ◽  
Layer Chromatography

In this study, the synthesis of a telechelic linker bearing both azide and thiol functional groups was described. The reaction conditions were investigated to optimize the reaction yield. The product was analyzed using thin layer chromatography (TLC) and proton nuclear magnetic resonance (1H NMR). The employment of the obtained azide–thiol linker in heterogeneous polymer “click” functionalization was demonstrated for the first time, which was monitored by an online FT–IR method. The obtained telechelic azide–thiol linker is envisioned to be useful chemical tools to link macromolecular chains via orthogonal click reactions.

scholarly journals Synthesis of Triazoles by Electro-Assisted Click Reaction Using a Copper Foil Electrode

2021 ◽  
Author(s):  
Luceldi Carre-Rangel ◽  
Karla Espinoza ◽  
Mercedes Oropeza-Guzmán ◽  
Ignacio Rivero
Keyword(s):  
Copper Foil ◽  
Click Reaction ◽  
Reference Electrode ◽  
Process Efficiency ◽  
Water Medium ◽  
Click Reactions ◽  
Onset Potential ◽  
Wide Range ◽  
Biological Environment

This paper presents an innovative pathway for the synthesis of triazoles using the well-known “click chemistry” assisted by the electrochemical oxidation of metallic Cu0. The click reaction is used to couple a wide range of biological interest compounds. In this case, faster and less polluting methods for a biological environment was achived by in situ Cu0 electrooxidation, providing the suitable quantity of catalyst required by click reaction. The electrochemical cell was composed of a copper foil as the working electrode, a platinum wire serving as a counter electrode, and an Ag/AgCl wire as the reference electrode. Linear anodic sweep voltammetry in a tert-butanol-water medium (1:1), an electrolyte of tetrabutylammonium tetrafluoroborate (TBATFB), showed the onset potential of Cu0 electrooxidation. Using the same electrode configuration three different triazoles were prepared under constant electrode potential, in a short time (60 min), and splendid yields (78-90%). These results indicate that the in situ CuI formation occurs on the surface of the copper foil. A pulse potential program has also been implemented in which a yield of 92% was achieved, reducing electrode passivation and consequently increasing the process efficiency. The electroassisted click reactions are highly efficient to produce triazoles by an innovative electrochemical reaction. The products were characterized by infrared (IR), nuclear magnetic resonance (1H and 13C NMR), and mass spectrometry (MS).

scholarly journals Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches

2021 ◽  
Author(s):  
Patrick Pfaff ◽  
Felix Anderl ◽  
Moritz Fink ◽  
Moritz Balkenhohl ◽  
Erick Carreira
Keyword(s):  
Natural Products ◽  
Arachidonic Acid ◽  
Modular Approach ◽  
Complex Molecules ◽  
Design And Synthesis ◽  
Wide Range ◽  
Potential Applications ◽  
First Time ◽  
Oriented Approach

We report a modular approach towards novel arylazotriazole photoswitches and their photophysical characterization. Addition of lithiated TIPS-acetylene to aryldiazonium tetrafluoroborate salts gives a wide range of azoacetylenes, constituting an underexplored class of stable intermediates. <i>In situ </i>desilylation transiently leads to terminal arylazoacetylenes that undergo copper-catalyzed cycloadditions (CuAAC) with a diverse collection of organoazides. These include complex molecules derived from natural products or drugs, such as colchicine, taxol, tamiflu, and arachidonic acid. The arylazotriazoles display near-quantitative photoisomerization and long thermal <i>Z</i>-half-lives. Using the method, we introduce for the first time the design and synthesis of a diacetylene platform that permits implementation of a consecutive and diversity-oriented approach linking two different conjugants to independently addressable acetylenes within a common photoswitchable azotriazole. This is showcased in the synthesis of several photoswitchable conjugates, with potential applications as photoPROTACs and photoswitchable biotin conjugates

scholarly journals Azoacetylenes for the Synthesis of Arylazotriazole Photoswitches

2021 ◽  
Author(s):  
Patrick Pfaff ◽  
Felix Anderl ◽  
Moritz Fink ◽  
Moritz Balkenhohl ◽  
Erick Carreira
Keyword(s):  
Natural Products ◽  
Arachidonic Acid ◽  
Modular Approach ◽  
Complex Molecules ◽  
Design And Synthesis ◽  
Wide Range ◽  
Potential Applications ◽  
First Time ◽  
Oriented Approach

We report a modular approach towards novel arylazotriazole photoswitches and their photophysical characterization. Addition of lithiated TIPS-acetylene to aryldiazonium tetrafluoroborate salts gives a wide range of azoacetylenes, constituting an underexplored class of stable intermediates. <i>In situ </i>desilylation transiently leads to terminal arylazoacetylenes that undergo copper-catalyzed cycloadditions (CuAAC) with a diverse collection of organoazides. These include complex molecules derived from natural products or drugs, such as colchicine, taxol, tamiflu, and arachidonic acid. The arylazotriazoles display near-quantitative photoisomerization and long thermal <i>Z</i>-half-lives. Using the method, we introduce for the first time the design and synthesis of a diacetylene platform that permits implementation of a consecutive and diversity-oriented approach linking two different conjugants to independently addressable acetylenes within a common photoswitchable azotriazole. This is showcased in the synthesis of several photoswitchable conjugates, with potential applications as photoPROTACs and photoswitchable biotin conjugates

Quantitative end-group functionalization of PNIPAM from aqueous SET-LRP via in situ reduction of Cu(ii) with NaBH4

2016 ◽  
Vol 7 (29) ◽  
pp. 4802-4809 ◽  
Author(s):  
Mikhail Gavrilov ◽  
Zhongfan Jia ◽  
Virgil Percec ◽  
Michael J. Monteiro
Keyword(s):  
Click Reaction ◽  
In Situ Reduction ◽  
End Group Functionalization ◽  
Very High ◽  
End Group

Rapid in situ azidation and CuAAC ‘click’ reaction demonstrating very high chain-end functionality.

Probing the Dynamic Self-Assembly Behaviour of Photoswitchable Wormlike Micelles in Real Time

2018 ◽  
Author(s):  
Elaine A. Kelly ◽  
Judith E. Houston ◽  
Rachel Evans
Keyword(s):  
Real Time ◽  
Absorption Spectroscopy ◽  
Self Assembly ◽  
Uv Light ◽  
Wormlike Micelles ◽  
Tetraethylene Glycol ◽  
Light Illumination ◽  
First Time ◽  
Dependent Processes

Understanding the dynamic self-assembly behaviour of azobenzene photosurfactants (AzoPS) is crucial to advance their use in controlled release applications such as<i></i>drug delivery and micellar catalysis. Currently, their behaviour in the equilibrium <i>cis-</i>and <i>trans</i>-photostationary states is more widely understood than during the photoisomerisation process itself. Here, we investigate the time-dependent self-assembly of the different photoisomers of a model neutral AzoPS, <a>tetraethylene glycol mono(4′,4-octyloxy,octyl-azobenzene) </a>(C<sub>8</sub>AzoOC<sub>8</sub>E<sub>4</sub>) using small-angle neutron scattering (SANS). We show that the incorporation of <i>in-situ</i>UV-Vis absorption spectroscopy with SANS allows the scattering profile, and hence micelle shape, to be correlated with the extent of photoisomerisation in real-time. It was observed that C<sub>8</sub>AzoOC<sub>8</sub>E<sub>4</sub>could switch between wormlike micelles (<i>trans</i>native state) and fractal aggregates (under UV light), with changes in the self-assembled structure arising concurrently with changes in the absorption spectrum. Wormlike micelles could be recovered within 60 seconds of blue light illumination. To the best of our knowledge, this is the first time the degree of AzoPS photoisomerisation has been tracked <i>in</i><i>-situ</i>through combined UV-Vis absorption spectroscopy-SANS measurements. This technique could be widely used to gain mechanistic and kinetic insights into light-dependent processes that are reliant on self-assembly.

The Total Synthesis of Rhabdastrellic Acid A

2018 ◽  
Author(s):  
Yaroslav Boyko ◽  
Christopher Huck ◽  
David Sarlah
Keyword(s):  
Total Synthesis ◽  
Late Stage ◽  
Cross Coupling ◽  
Side Chains ◽  
General Strategy ◽  
Modular Approach ◽  
Linear Sequence ◽  
Generating Sequence ◽  
First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

scholarly journals Engineered Phage Endolysin Eliminates Gardnerella Biofilm without Damaging Beneficial Bacteria in Bacterial Vaginosis Ex Vivo

Pathogens ◽  
2021 ◽  
Vol 10 (1) ◽  
pp. 54
Author(s):  
Christine Landlinger ◽  
Lenka Tisakova ◽  
Vera Oberbauer ◽  
Timo Schwebs ◽  
Abbas Muhammad ◽  
...  
Keyword(s):  
Bacterial Vaginosis ◽  
Bactericidal Activity ◽  
High Selectivity ◽  
Ex Vivo ◽  
Vaginal Microbiome ◽  
Wild Type ◽  
Wild Type Enzyme ◽  
Promising Alternative ◽  
First Time

Bacterial vaginosis is characterized by an imbalance of the vaginal microbiome and a characteristic biofilm formed on the vaginal epithelium, which is initiated and dominated by Gardnerella bacteria, and is frequently refractory to antibiotic treatment. We investigated endolysins of the type 1,4-beta-N-acetylmuramidase encoded on Gardnerella prophages as an alternative treatment. When recombinantly expressed, these proteins demonstrated strong bactericidal activity against four different Gardnerella species. By domain shuffling, we generated several engineered endolysins with 10-fold higher bactericidal activity than any wild-type enzyme. When tested against a panel of 20 Gardnerella strains, the most active endolysin, called PM-477, showed minimum inhibitory concentrations of 0.13–8 µg/mL. PM-477 had no effect on beneficial lactobacilli or other species of vaginal bacteria. Furthermore, the efficacy of PM-477 was tested by fluorescence in situ hybridization on vaginal samples of fifteen patients with either first time or recurring bacterial vaginosis. In thirteen cases, PM-477 killed the Gardnerella bacteria and physically dissolved the biofilms without affecting the remaining vaginal microbiome. The high selectivity and effectiveness in eliminating Gardnerella, both in cultures of isolated strains as well as in clinically derived samples of natural polymicrobial biofilms, makes PM-477 a promising alternative to antibiotics for the treatment of bacterial vaginosis, especially in patients with frequent recurrence.

scholarly journals Chromosomal painting of the sandpiper (Actitis macularius) detects several fissions for the Scolopacidae family (Charadriiformes)

2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Melquizedec Luiz Silva Pinheiro ◽  
Cleusa Yoshiko Nagamachi ◽  
Talita Fernanda Augusto Ribas ◽  
Cristovam Guerreiro Diniz ◽  
Patricia Caroline Mary O´Brien ◽  
...  
Keyword(s):  
Chromosome Painting ◽  
Diploid Number ◽  
Chromosomal Evolution ◽  
Long Distance ◽  
Chromosomal Painting ◽  
Cytogenetic Studies ◽  
Burhinus Oedicnemus ◽  
Clear Idea ◽  
First Time

Abstract Background The Scolopacidae family (Suborder Scolopaci, Charadriiformes) is composed of sandpipers and snipes; these birds are long-distance migrants that show great diversity in their behavior and habitat use. Cytogenetic studies in the Scolopacidae family show the highest diploid numbers for order Charadriiformes. This work analyzes for the first time the karyotype of Actitis macularius by classic cytogenetics and chromosome painting. Results The species has a diploid number of 92, composed mostly of telocentric pairs. This high 2n is greater than the proposed 80 for the avian ancestral putative karyotype (a common feature among Scolopaci), suggesting that fission rearrangements have formed smaller macrochromosomes and microchromosomes. Fluorescence in situ hybridization using Burhinus oedicnemus whole chromosome probes confirmed the fissions in pairs 1, 2, 3, 4 and 6 of macrochromosomes. Conclusion Comparative analysis with other species of Charadriiformes studied by chromosome painting together with the molecular phylogenies for the order allowed us to raise hypotheses about the chromosomal evolution in suborder Scolopaci. From this, we can establish a clear idea of how chromosomal evolution occurred in this suborder.

Catalytic dehydrogenation of amines to imines and the in-situ reduction of sulfoxides into sulfides

2021 ◽  
Author(s):  
Xixi Liu ◽  
Yanxin Wang ◽  
Bo Li ◽  
Bing Liu ◽  
Wei Wang ◽  
...  
Keyword(s):  
Catalytic Dehydrogenation ◽  
In Situ Reduction
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