scholarly journals Synthesis and Characterization of a Novel Biheterocyclic -amino Acid Precursor of the Triazole-Tetrazole Type, via the Copper (I) Catalyzed Alkyne-Azide Cycloaddition Reaction (CuAAC)

2021 ◽  
Vol 2 (2) ◽  
pp. 7-15
Author(s):  
Khadim Dioukhane ◽  
Younas Aouine ◽  
Salaheddine Boukhssas ◽  
Asmae Nakkabi ◽  
Hassane Faraj ◽  
...  
Keyword(s):  
Amino Acid ◽  
Cycloaddition Reaction ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Resonance Spectroscopy ◽  
Compound A ◽  
Amino Acid Precursor ◽  
Acid Precursor

In this paper, we describe the regioselective synthesis of a novel tri-heterocyclic compound, a biheterocyclic amino acid precursor, derived from both triazole and tetrazole. The key step of our synthesis approach was the Huigsen 1,3-dipolar cycloaddition reaction, catalyzed by the copper (I) formed in situ by reduction of Cu(II) salts (CuSO4), 5H2O) by sodium ascorbate, and using as dipole the oxazoline azide derivative 4-(azidomethyl)-4-ethyl-2-phenyl-4,5-dihydrooxazole (4) and as dipolarophile 5-(4-methoxyphenyl)-2-(prop-2-yn-1-yl)-2H-tetrazole (3).  The Cu(I) catalysis allowed us to carry out the cycloaddition at room temperature during a reaction time of only 8 hours and also to selectively obtain the 1,4-regioisomer; one of the two possible isomers, with a yield of 90% after chromatography on a silica gel column (ether/hexane: 1/2), and recrystallization in an ether/acetone mixture. The desired compound, 4-ethyl-4-((4-((5-(4-methoxyphenyl)-2H-tetrazol-2-yl)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2-phenyl-4,5-dihydrooxazole (5) was analyzed by 1D magnetic resonance spectroscopy (1H, 13C), and characterized physico-chemically by mass spectrometry and elemental analysis.

scholarly journals Diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate

Molbank ◽  
10.3390/m1167 ◽  
2020 ◽  
Vol 2020 (4) ◽  
pp. M1167
Author(s):  
Serigne Abdou Khadir Fall ◽  
Saïd Achamlale ◽  
Younas Aouine ◽  
Asmae Nakkabi ◽  
Hassane Faraj ◽  
...  
Keyword(s):  
Infrared Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Solvent Mixture ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Sulfate Pentahydrate ◽  
Copper Sulfate Pentahydrate

The title compound, diethyl [(4-{(9H-carbazol-9-yl)methyl}-1H-1,2,3-triazol-1-yl)(benzamido)methyl]phosphonate, was synthesized with excellent yield and high regioselectivity through 1,3-dipolar cycloaddition reaction between the α-azido diethyl amino methylphosphonate and the heterocyclic alkyne, 9-(prop-2-yn-1-yl)-9H-carbazole. The cyclization reaction by “click chemistry” was carried out in a water/ethanol solvent mixture (50/50), in the presence of copper sulfate pentahydrate and catalytic sodium ascorbate. The characterization of the structure of the resulting 1,4-regioisomer was performed by 1D and 2D-NMR experiments, infrared spectroscopy, and elemental analysis.

scholarly journals Characterization of Garvicin ML, a Novel Circular Bacteriocin Produced byLactococcus garvieaeDCC43, Isolated from Mallard Ducks (Anas platyrhynchos)

2010 ◽  
Vol 77 (1) ◽  
pp. 369-373 ◽  
Author(s):  
Juan Borrero ◽  
Dag A. Brede ◽  
Morten Skaugen ◽  
Dzung B. Diep ◽  
Carmen Herranz ◽  
...  
Keyword(s):  
Amino Acid ◽  
Reverse Genetics ◽  
De Novo ◽  
Leader Peptide ◽  
Nucleotide Sequencing ◽  
Amino Acid Sequencing ◽  
Circular Bacteriocin ◽  
Amino Acid Precursor ◽  
Acid Precursor

ABSTRACTLactococcus garvieaeDCC43 produces a bacteriocin, garvicin ML (GarML), with a molecular mass of 6,004.2 Da. Data fromde novoamino acid sequencing by tandem mass spectrometry and nucleotide sequencing by reverse genetics suggested that the bacteriocin is synthesized as a 63-amino-acid precursor with a 3-amino-acid leader peptide that is removed by cleavage. Subsequently, a covalent linkage between the N and C termini forms the mature version of this novel 60-amino-acid circular bacteriocin.

scholarly journals Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation

2017 ◽  
Vol 67 (3) ◽  
pp. 309-324 ◽  
Author(s):  
Nadjet Rezki ◽  
Mohamed Reda Aouad
Keyword(s):  
Antimicrobial Activity ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
One Pot ◽  
Alkyl Aryl ◽  
Antimicrobial Evaluation ◽  
Ultrasound Assisted ◽  
Click Synthesis

AbstractThe present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles4a-ethrough a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involvesin situgeneration of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates6a-owere recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.

scholarly journals The Blue Copper-Containing Nitrite Reductase fromAlcaligenes xylosoxidans: Cloning of the nirAGene and Characterization of the Recombinant Enzyme

1999 ◽  
Vol 181 (8) ◽  
pp. 2323-2329 ◽  
Author(s):  
Miguel Prudêncio ◽  
Robert R. Eady ◽  
Gary Sawers
Keyword(s):  
Amino Acid ◽  
Nitrite Reductase ◽  
Recombinant Enzyme ◽  
Leader Peptide ◽  
Resonance Spectroscopy ◽  
Gene Encoding ◽  
Blue Copper

ABSTRACT The nirA gene encoding the blue dissimilatory nitrite reductase from Alcaligenes xylosoxidans has been cloned and sequenced. To our knowledge, this is the first report of the characterization of a gene encoding a blue copper-containing nitrite reductase. The deduced amino acid sequence exhibits a high degree of similarity to other copper-containing nitrite reductases from various bacterial sources. The full-length protein included a 24-amino-acid leader peptide. The nirA gene was overexpressed inEscherichia coli and was shown to be exported to the periplasm. Purification was achieved in a single step, and analysis of the recombinant Nir enzyme revealed that cleavage of the signal peptide occurred at a position identical to that for the native enzyme isolated from A. xylosoxidans. The recombinant Nir isolated directly was blue and trimeric and, on the basis of electron paramagnetic resonance spectroscopy and metal analysis, possessed only type 1 copper centers. This type 2-depleted enzyme preparation also had a low nitrite reductase enzyme activity. Incubation of the periplasmic fraction with copper sulfate prior to purification resulted in the isolation of an enzyme with a full complement of type 1 and type 2 copper centers and a high specific activity. The kinetic properties of the recombinant enzyme were indistinguishable from those of the native nitrite reductase isolated from A. xylosoxidans. This rapid isolation procedure will greatly facilitate genetic and biochemical characterization of both wild-type and mutant derivatives of this protein.

Catecholated graphene-filled polyimide with enhanced mechanical, thermal, and tribological properties

2020 ◽  
pp. 095400832094035
Author(s):  
Xing Wu ◽  
Zhengyu Jin ◽  
Yuejin Zhu ◽  
Haichao Zhao
Keyword(s):  
Friction And Wear ◽  
In Situ Polymerization ◽  
Cycloaddition Reaction ◽  
Mechanical Analysis ◽  
Dipolar Cycloaddition ◽  
Wear Properties ◽  
Comprehensive Properties ◽  
Transmission Electron ◽  
Friction And Wear Tests

In order to achieve good dispersion of graphene in polyimide (PI), catecholated graphene (G-Cat) was prepared by 1,3-dipolar cycloaddition reaction of N-methylglycine and 3,4-dihydroxybenzaldehyde with graphene sheets. G-Cat/PI composites were prepared by in situ polymerization with pyromellitic dianhydride and 4,4-oxydianiline in the presence of G-Cat. The successful modification of graphene was proved by infrared spectroscopy, Raman spectroscopy, and transmission electron microscopy. The comprehensive properties of G-Cat/PI composites were studied by tensile, dynamic mechanical analysis, thermogravimetric analysis, and friction and wear tests. By observing the morphology of wear marks, the friction and wear properties of the composites were emphatically analyzed. Therefore, graphene/PI composites were expected to have broad application prospects in lubrication and wear resistance.

scholarly journals Characterization of neutrophilb-type cytochrome in situ by electron paramagnetic resonance spectroscopy

FEBS Letters ◽  
1991 ◽  
Vol 281 (1-2) ◽  
pp. 130-132 ◽  
Author(s):  
Ikuko Ueno ◽  
Satoshi Fujii ◽  
Hiroaki Ohya-Nishiguchi ◽  
Tetsutaro Iizuka ◽  
Shiro Kanegasaki
Keyword(s):  
Electron Paramagnetic Resonance ◽  
Electron Paramagnetic Resonance Spectroscopy ◽  
Resonance Spectroscopy ◽  
Paramagnetic Resonance ◽  
Electron Paramagnetic

Uranyl triazolate formation via an in situ Huisgen 1,3-dipolar cycloaddition reaction

CrystEngComm ◽  
2011 ◽  
Vol 13 (1) ◽  
pp. 153-157 ◽  
Author(s):  
Karah E. Knope ◽  
Christopher L. Cahill
Keyword(s):  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition

Synthesis of New Hexakis-Heterocyclic Compounds and their Use in the Formation and Stabilization of Au and Ag Nanoparticles

2014 ◽  
Vol 976 ◽  
pp. 3-7
Author(s):  
María Isabel Montalvo-Sierra ◽  
Miriam A. Martins Alho ◽  
Ana María Herrera-Gonzalez ◽  
Jesús García-Serrano ◽  
Paola Belem Bocardo-Tovar
Keyword(s):  
Ir Spectroscopy ◽  
Ag Nanoparticles ◽  
Heterocyclic Compounds ◽  
Cyano Group ◽  
Cycloaddition Reaction ◽  
Aldehyde Group ◽  
Dipolar Cycloaddition ◽  
Vis Spectroscopy ◽  
Aldehyde Derivative

The stabilization of nanoparticles in solution is a challenge of major proportions, and avoiding the formation of aggregates and eventual coalescence of particles is directly linked to the conservation of its unique properties. In this work, we reported the synthesis of two hexakis-heterocyclic compounds, containing the tetrazole or 2-amino-1,3,4-thiadiazole group, respectively. The hexa-heterocyclic compounds were used in the synthesis and stabilization of Au and Ag nanoparticles. To obtain these molecules was used phosphonitrilic chloride trimer compound as core, which reacted with phenols properly substituted in theparaposition with either cyano or aldehyde group. The cyano group was successfully converted to the corresponding tetrazole using a 1,3-dipolar cycloaddition reaction with ammonium azide generatedin situ. In the case of aldehyde derivative, it was converted to the corresponding thiosemicarbazone, which was further cyclized using FeCl3. Compounds were characterized by RMN and IR spectroscopy. The UV-Vis spectroscopy was used for nanoparticles analysis.

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