scholarly journals Structural and Serological Studies of the O6-Related Antigen of Aeromonas veronii bv. sobria Strain K557 Isolated from Cyprinus carpio on a Polish Fish Farm, which Contains L-perosamine (4-amino-4,6-dideoxy-L-mannose), a Unique Sugar Characteristic for Aeromonas Serogroup O6

Marine Drugs ◽  
2019 ◽  
Vol 17 (7) ◽  
pp. 399 ◽  
Author(s):  
Dworaczek ◽  
Drzewiecka ◽  
Pękala-Safińska ◽  
Turska-Szewczuk
Keyword(s):  
Mass Spectrometry ◽  
13C Nmr Spectroscopy ◽  
Fish Farm ◽  
Chemical Analyses ◽  
1H And 13C Nmr ◽  
O Antigen ◽  
Aeromonas Veronii ◽  
Serological Studies ◽  
Specific Polysaccharide ◽  
Mild Acid

Amongst Aeromonas spp. strains that are pathogenic to fish in Polish aquacultures, serogroup O6 was one of the five most commonly identified immunotypes especially among carp isolates. Here, we report immunochemical studies of the lipopolysaccharide (LPS) including the O-specific polysaccharide (O-antigen) of A. veronii bv. sobria strain K557, serogroup O6, isolated from a common carp during an outbreak of motile aeromonad septicemia (MAS) on a Polish fish farm. The O-polysaccharide was obtained by mild acid degradation of the LPS and studied by chemical analyses, mass spectrometry, and 1H and 13C NMR spectroscopy. It was revealed that the O-antigen was composed of two O-polysaccharides, both containing a unique sugar 4-amino-4,6-dideoxy-L-mannose (N-acetyl-L-perosamine, L-Rhap4NAc). The following structures of the O-polysaccharides (O-PS 1 and O-PS 2) were established:

scholarly journals Structural Studies of the Lipopolysaccharide of Aeromonas veronii bv. sobria Strain K133 which Represents New Provisional Serogroup PGO1 Prevailing among Mesophilic Aeromonads on Polish Fish Farms

2021 ◽  
Vol 22 (8) ◽  
pp. 4272
Author(s):  
Katarzyna Dworaczek ◽  
Maria Kurzylewska ◽  
Magdalena Laban ◽  
Dominika Drzewiecka ◽  
Agnieszka Pękala-Safińska ◽  
...  
Keyword(s):  
Epidemiological Data ◽  
13C Nmr Spectroscopy ◽  
Freshwater Species ◽  
Fish Farms ◽  
1H And 13C Nmr ◽  
Aeromonas Veronii ◽  
Specific Polysaccharide ◽  
O Antigens ◽  
Unique Composition

In the present work, we performed immunochemical studies of LPS, especially the O-specific polysaccharide (O-PS) of Aeromonas veronii bv. sobria strain K133, which was isolated from the kidney of carp (Cyprinus carpio L.) during an outbreak of motile aeromonad infection/motile aeromonad septicemia (MAI/MAS) on a Polish fish farm. The structural characterization of the O-PS, which was obtained by mild acid degradation of the LPS, was performed with chemical methods, MALDI-TOF mass spectrometry, and 1H and 13C NMR spectroscopy. It was revealed that the O-PS has a unique composition of a linear tetrasaccharide repeating unit and contains a rarely occurring sugar 2,4-diamino-2,4,6-trideoxy-D-glucose (bacillosamine), which may determine the specificity of the serogroup. Western blotting and ELISA confirmed that A. veronii bv. sobria strain K133 belongs to the new serogroup PGO1, which is one of the most commonly represented immunotypes among carp and trout isolates of Aeromonas sp. in Polish aquacultures. Considering the increase in the MAI/MAS incidences and their impact on freshwater species, also with economic importance, and in the absence of an effective immunoprophylaxis, studies of the Aeromonas O-antigens are relevant in the light of epidemiological data and monitoring emergent pathogens representing unknown antigenic variants and serotypes.

scholarly journals Structure of the 4-O-[1-Carboxyethyl]-d-Mannose-Containing O-Specific Polysaccharide of a Halophilic Bacterium Salinivibrio sp. EG9S8QL

Marine Drugs ◽  
2021 ◽  
Vol 19 (9) ◽  
pp. 508
Author(s):  
Elena N. Sigida ◽  
Ibrahim M. Ibrahim ◽  
Maxim S. Kokoulin ◽  
Hussein H. Abulreesh ◽  
Khaled Elbanna ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
13C Nmr Spectroscopy ◽  
Halophilic Bacterium ◽  
Mild Acid Hydrolysis ◽  
1H And 13C Nmr ◽  
Specific Polysaccharide ◽  
Lake Qarun ◽  
Phenol Water ◽  
Hydrolysis Of ◽  
Mild Acid

The moderately halophilic strain Salinivibrio sp. EG9S8QL was isolated among 11 halophilic strains from saline mud (Emisal Salt Company, Lake Qarun, Fayoum, Egypt). The lipopolysaccharide was extracted from dried cells of Salinivibrio sp. EG9S8QL by the phenol–water procedure. The OPS was obtained by mild acid hydrolysis of the lipopolysaccharide and was studied by sugar analysis along with 1H and 13C NMR spectroscopy, including 1H,1H COSY, TOCSY, ROESY, 1H,13C HSQC, and HMBC experiments. The OPS was found to be composed of linear tetrasaccharide repeating units of the following structure: →2)-β-Manp4Lac-(1→3)-α-ManpNAc-(1→3)-β-Rhap-(1→4)-α-GlcpNAc-(1→, where Manp4Lac is 4-O-[1-carboxyethyl]mannose.

scholarly journals A Unique Sugar l-Perosamine (4-Amino-4,6-dideoxy-l-mannose) Is a Compound Building Two O-Chain Polysaccharides in the Lipopolysaccharide of Aeromonas hydrophila Strain JCM 3968, Serogroup O6

Marine Drugs ◽  
2019 ◽  
Vol 17 (5) ◽  
pp. 254 ◽  
Author(s):  
Katarzyna Dworaczek ◽  
Maria Kurzylewska ◽  
Magdalena A. Karaś ◽  
Monika Janczarek ◽  
Agnieszka Pękala-Safińska ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Aeromonas Hydrophila ◽  
Lipid A ◽  
Gel Permeation Chromatography ◽  
13C Nmr Spectroscopy ◽  
Bacterial Strains ◽  
Core Oligosaccharide ◽  
O Antigen ◽  
Specific Polysaccharide ◽  
Exposed Part

Lipopolysaccharide (LPS) is the major glycolipid and virulence factor of Gram-negative bacteria, including Aeromonas spp. The O-specific polysaccharide (O-PS, O-chain, O-antigen), i.e., the surface-exposed part of LPS, which is a hetero- or homopolysaccharide, determines the serospecificity of bacterial strains. Here, chemical analyses, mass spectrometry, and 1H and 13C NMR spectroscopy techniques were employed to study the O-PS of Aeromonas hydrophila strain JCM 3968, serogroup O6. MALDI-TOF mass spectrometry revealed that the LPS of A. hydrophila JCM 3968 has a hexaacylated lipid A with conserved architecture of the backbone and a core oligosaccharide composed of Hep6Hex1HexN1HexNAc1Kdo1P1. To liberate the O-antigen, LPS was subjected to mild acid hydrolysis followed by gel-permeation-chromatography and revealed two O-polysaccharides that were found to contain a unique sugar 4-amino-4,6-dideoxy-l-mannose (N-acetyl-l-perosamine, l-Rhap4NAc), which may further determine the specificity of the serogroup. The first O-polysaccharide (O-PS1) was built up of trisaccharide repeating units composed of one α-d-GalpNAc and two α-l-Rhap4NAc residues, whereas the other one, O-PS2, is an α1→2 linked homopolymer of l-Rhap4NAc. The following structures of the O-polysaccharides were established: O-PS1 →3)-α-l-Rhap4NAc-(1→4)-α-d-GalpNAc-(1→3)-α-l-Rhap4NAc-(1→ O-PS2 →2)-α-l-Rhap4NAc-(1→ The present paper is the first work that reveals the occurrence of perosamine in the l-configuration as a component of bacterial O-chain polysaccharides.

scholarly journals (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

Molbank ◽  
10.3390/m1140 ◽  
2020 ◽  
Vol 2020 (2) ◽  
pp. M1140
Author(s):  
Jack Bennett ◽  
Paul Murphy
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Ir Spectroscopy ◽  
13C Nmr ◽  
Conjugate Addition ◽  
13C Nmr Spectroscopy ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Esi Mass Spectrometry ◽  
The One

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

scholarly journals N-[2-(1H-Indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide

Molbank ◽  
10.3390/m1008 ◽  
2018 ◽  
Vol 2018 (3) ◽  
pp. M1008
Author(s):  
Nikil Purushotham ◽  
Boja Poojary
Keyword(s):  
Mass Spectrometry ◽  
Mycobacterium Tuberculosis ◽  
Potassium Hydroxide ◽  
Inhibitory Action ◽  
13C Nmr Spectroscopy ◽  
Enoyl Reductase ◽  
1H And 13C Nmr ◽  
Ft Ir ◽  
Non Covalent Interactions ◽  
Covalent Interactions

N-[1-Hydrazinyl-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-4-methylbenzenesulfonamide (1) on cyclization with carbon disulfide in ethanolic potassium hydroxide affords N-[2-(1H-indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide (2) in 84% yield. The structure of compound 2 was supported by mass spectrometry, FT-IR and 1H- and 13C-NMR spectroscopy. To investigate the potential of compound 2 to act as antitubercular agent, it was docked against the enoyl reductase (InhA) enzyme of Mycobacterium tuberculosis. The docking pose and non-covalent interactions gave insights on its plausible inhibitory action.

3-Amino-2-methylquinazolin-4-(3H)-one Schiff Bases Synthesis – a Green Chemistry Approach – a Comparison of Microwave and Ultrasound Promoted Synthesis with Mechanosynthesis.

2020 ◽  
Vol 07 ◽  
Author(s):  
Mario Komar ◽  
Fran Prašnikar ◽  
Tatjana Gazivoda Kraljević ◽  
Krunoslav Aladić ◽  
Maja Molnar
Keyword(s):  
Mass Spectrometry ◽  
Green Chemistry ◽  
Schiff Bases ◽  
13C Nmr Spectroscopy ◽  
Synthetic Methods ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Microwave Assisted ◽  
Ultrasound Assisted ◽  
High Yields

: A green chemistry methods are important modern pathways in synthetic chemistry with main advantages such as milder reaction conditions, shorter time and higher yields. A series of quinazolinone based Schiff bases (1−27) have been successfully synthesized by using green synthetic methods including microwave-assisted, ultrasound-assisted and mechanochemical synthesis, respectively. Desired compounds were prepared from 3-amino-2-methylquinazolin-4(3H)- one and substituted benzaldehydes with moderate to high yields (11−90%). Benzoxazinone and 3-amino-2- methylquinazolin-4(3H)-one, the precursors of Schiff bases, were prepared by microwave induced synthesis. The structures of all Schiff bases are confirmed by 1H and 13C NMR spectroscopy and mass spectrometry as well. A novelty of this research is the application and comparison of green chemistry methods in the synthesis of desired compounds are listed above. The simplicity of synthesis includes ethanol as solvent and no need for further purification.

scholarly journals 4-[(3,4-Dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione

Molbank ◽  
10.3390/m1055 ◽  
2019 ◽  
Vol 2019 (1) ◽  
pp. M1055
Author(s):  
Soukhyarani Nayak ◽  
Boja Poojary
Keyword(s):  
Mass Spectrometry ◽  
Inhibitory Action ◽  
Noncovalent Interactions ◽  
Catalytic Amount ◽  
13C Nmr Spectroscopy ◽  
Target Compound ◽  
Solid Product ◽  
1H And 13C Nmr ◽  
Elemental Analyses ◽  
Ft Ir

4-Amino-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (1) upon treatment with 3,4-dimethoxybenzaldehyde in 10 mL of absolute ethanol in the presence of a catalytic amount of acetic acid produced the target compound 4-[(3,4-dimethoxybenzylidene)amino]-5-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (2) in 80% yield. The obtained solid product was recrystallized from ethanol. The compound was characterized by elemental analyses, mass spectrometry, FT-IR, 1H and 13C-NMR spectroscopy. To study the binding interactions of the compound with receptor, it was docked with the human prostaglandin reductase (PTGR2). The docking pose and noncovalent interactions gave insights into its plausible inhibitory action.

scholarly journals Synthesis and Structural Features of 3(5)-alkyl(aryl)-5(3)-pyridyl-4-nitroso-1Н-pyrazoles

2021 ◽  
pp. 218-225
Author(s):  
Darya S. Volkova ◽  
Anna S. Kositsyna ◽  
Kukushkin, Alexey A. Kukushkin ◽  
Evgeniy V. Root
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Hydrazine Hydrate ◽  
13C Nmr ◽  
13C Nmr Spectroscopy ◽  
Structural Features ◽  
Alkyl Aryl ◽  
Dicarbonyl Compounds ◽  
1H And 13C Nmr ◽  
Modern Methods

А para-chlorophenyl substituent was firstly obtained into the structure of pyridyl-substituted 4-nitrosopyrazole by cyclocondensation of hydrazine hydrate with the corresponding isonitroso-β-dicarbonyl compounds. The structure of previously unknown 3(5)-(4-chlorophenyl)-5(3)-pyridine-(3(4))-yl-4-nitroso-1H-pyrazoles and previously obtained 3(5)-alkyl(aryl)-5(3)-pyridine-(3(4))-yl-4-nitroso-1H-pyrazoles is proved and studied in detail by modern methods of analysis: mass spectrometry, 1H- and 13C NMR-spectroscopy

scholarly journals Synthesis of a new serie of quinoline-carboxamides based on methylated aminoesters: NMR characterization and antimicrobial activity

2019 ◽  
Vol 9 (4) ◽  
pp. 326-336 ◽  
Author(s):  
Oussama Moussaoui ◽  
El Mestafa El Hadrami ◽  
Ghita Benjalloune Touimi ◽  
Bahia Bennani ◽  
Abdeslem Ben Tama ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Antimicrobial Activity ◽  
Room Temperature ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Antibacterial Activities ◽  
Amino Ester ◽  
1H And 13C Nmr ◽  
Nmr Characterization

Ten new quinoline-carboxamides have been synthesized using the coupling reaction between  2-oxo-1,2-dihydroquinoline-4-carboxylic acid as a substrate and five different amino ester at room temperature with basic media (triethylamine). The products were obtained with a good yield ranging from 60 to 80 % and were structurally characterized by 1H and 13C NMR spectroscopy and mass spectrometry. The antibacterial activities of the synthesized compounds have been evaluated against 9 strains of bacteria and compared to references (erythromycin, ofloxacin, ticarcillin, oxacillin, ampicillin, norfloxacin, ceftazidim, cefotaxim). The results showed that the majority of carboxamides-quinoline ester groups present a larger inhibition diameters than those of the antibiotics references. The highest antibacterial activity in vitro against the Enterococcus feacalis has been revealed for compound 1a (methyl 2-oxo-1.2-dihydroquinoline-4-yl-L-alaninate).

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