Synthesis and ATRP of novel fluorinated aromatic monomer with pendant sulfonate group

2013 ◽  
Vol 149 ◽  
pp. 30-35 ◽  
Author(s):  
Ivaylo Dimitrov ◽  
Katja Jankova ◽  
Søren Hvilsted
Keyword(s):  
Sulfonate Group ◽  
Aromatic Monomer

Polyamides containing a biorenewable aromatic monomer based on coumalate esters: from synthesis to evaluation of the thermal and mechanical properties

2021 ◽  
Vol 12 (16) ◽  
pp. 2379-2388
Author(s):  
Jules Stouten ◽  
Aleksandra A. Wróblewska ◽  
Glenn Grit ◽  
Jurrie Noordijk ◽  
Bert Gebben ◽  
...  
Keyword(s):  
Mechanical Properties ◽  
Propionic Acid ◽  
Terephthalic Acid ◽  
Thermal And Mechanical Properties ◽  
Aromatic Polyamides ◽  
Aromatic Monomer

A new biobased alternative for terephthalic acid (TPA) in (semi-)aromatic polyamides is proposed, namely 4-carboxybenzene propionic acid (4CBPA).

Effect of Catalyst Support on Aromatic Monomer Production from Lignocellulosic Biomass Over Pt-Based Catalysts

2021 ◽  
Author(s):  
Kiyoyuki Yamazaki ◽  
Ryuto Sasaki ◽  
Tatsuya Watanabe ◽  
Satoko Kuwano ◽  
Yuka Murakami ◽  
...  
Keyword(s):  
Lignocellulosic Biomass ◽  
Catalyst Support ◽  
Aromatic Monomer

scholarly journals Crystal structure of 2,4-dinitrophenyl 4-methylbenzenesulfonate: a new polymorph

2015 ◽  
Vol 71 (9) ◽  
pp. 1085-1088 ◽  
Author(s):  
Tyler A. Cooley ◽  
Sean Riley ◽  
Shannon M. Biros ◽  
Richard J. Staples ◽  
Felix N. Ngassa
Keyword(s):  
Crystal Structure ◽  
Nucleophilic Substitution ◽  
Torsion Angle ◽  
Title Compound ◽  
Substitution Reaction ◽  
Sulfonate Group ◽  
Acta Cryst ◽  
Crystal Stability ◽  
Compound C ◽  
Centroid Distance

The title compound, C13H10N2O7S, was synthesizedviaa nucleophilic substitution reaction between 2,4-dinitrophenol andp-toluenesulfonyl chloride. This crystal structure is a polymorph of CSD entry WUVYUH [Vembuet al.(2003).Acta Cryst, E59, o378–380]. The aromatic substituents on the sulfonate group are orientedgaucheto one another with a C—O—S—C torsion angle of −62.0 (3)°. The supramolecular features that contribute to the crystal stability are offset π–π [centroid–centroid distance = 3.729 (2) Å] and multiple C—H...O interactions.

scholarly journals The First Berberine-Based Inhibitors of Tyrosyl-DNA Phosphodiesterase 1 (Tdp1), an Important DNA Repair Enzyme

2020 ◽  
Vol 21 (19) ◽  
pp. 7162
Author(s):  
Elizaveta D. Gladkova ◽  
Ivan V. Nechepurenko ◽  
Roman A. Bredikhin ◽  
Arina A. Chepanova ◽  
Alexandra L. Zakharenko ◽  
...  
Keyword(s):  
Dna Repair ◽  
Bromine Atom ◽  
Sulfonate Group ◽  
Repair Enzyme ◽  
Topoisomerase 1 ◽  
Relationship Analysis ◽  
Low Toxicity ◽  
Berberine Derivatives ◽  
Further Development ◽  
Micromolar Range

A series of berberine and tetrahydroberberine sulfonate derivatives were prepared and tested against the tyrosyl-DNA phosphodiesterase 1 (Tdp1) DNA-repair enzyme. The berberine derivatives inhibit the Tdp1 enzyme in the low micromolar range; this is the first reported berberine based Tdp1 inhibitor. A structure–activity relationship analysis revealed the importance of bromine substitution in the 12-position on the tetrahydroberberine scaffold. Furthermore, it was shown that the addition of a sulfonate group containing a polyfluoroaromatic moiety at position 9 leads to increased potency, while most of the derivatives containing an alkyl fragment at the same position were not active. According to the molecular modeling, the bromine atom in position 12 forms a hydrogen bond to histidine 493, a key catalytic residue. The cytotoxic effect of topotecan, a clinically important topoisomerase 1 inhibitor, was doubled in the cervical cancer HeLa cell line by derivatives 11g and 12g; both displayed low toxicity without topotecan. Derivatives 11g and 12g can therefore be used for further development to sensitize the action of clinically relevant Topo1 inhibitors.

scholarly journals Crystal structure of zwitterionic 2-[bis(2-methoxyphenyl)phosphaniumyl]-4-methylbenzenesulfonate monohydrate dichloromethane monosolvate

2016 ◽  
Vol 72 (2) ◽  
pp. 229-232
Author(s):  
Hongyang Zhang ◽  
Ge Feng ◽  
Alexander S. Filatov ◽  
Richard F. Jordan
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Intermolecular Interactions ◽  
Title Compound ◽  
Water Molecules ◽  
Sulfonate Group ◽  
Centrosymmetric Dimer ◽  
Bond Lengths ◽  
Compound C

In the title compound, C21H21O5PS·H2O·CH2Cl2, the phosphonium–sulfonate zwitterion has the acidic H atom located on the P atom rather than the sulfonate group. The S—O bond lengths [1.4453 (15)–1.4521 (14) Å] are essentially equal. In the crystal, the water molecules bridge two zwitterionsviaOwater—H...Osulfonatehydrogen bonds into a centrosymmetric dimer. The dimers are further linked by weak CAryl—H...Osulfonatehydrogen bonds into chains extending along [100]. The PH+group is not involved in intermolecular interactions.

scholarly journals Microwave Enhanced Synthesis of Sulfonated Chitosan-montmorillonite for Effective Removal of Methylene Blue

2021 ◽  
Author(s):  
Nur Shazwani Abdul Mubarak ◽  
N.N. Bahrudin ◽  
Ali H. Jawad ◽  
B.H. Hameed ◽  
Sumiyyah Sabar
Keyword(s):  
Methylene Blue ◽  
Langmuir Isotherm ◽  
Cationic Dyes ◽  
Isotherm Model ◽  
Batch Adsorption ◽  
Sulfonate Group ◽  
Order Kinetic ◽  
Effective Removal ◽  
Langmuir Isotherm Model ◽  
Mb Adsorption

Abstract In this work, sulfonated chitosan montmorillonite composite (S-CS-MT) beads were synthesized using a microwave irradiation method designed to have a better saving-time procedure. The potency of S-CS-MT as an adsorbent was assessed for the removal of cationic dyes such as methylene blue (MB) from aqueous solution. The batch adsorption experiments indicated that MB adsorption onto S-CS-MT follows the Pseudo-second-order kinetic and Langmuir isotherm model. The maximum extent obtained from the Langmuir isotherm model for MB adsorption was 188.2 mg g− 1 at 303 K. The thermodynamic study indicated that the adsorption reaction is favorable and spontaneous. These findings indicated that montmorillonite chitosan grafted with the sulfonate group has the ability and efficacy as biohybrid adsorbent for the adsorption of cationic dyes.

Mixed-mode liquid chromatography with a stationary phase co-functionalized with ionic liquid embedded C18 and an aryl sulfonate group

2018 ◽  
Vol 1564 ◽  
pp. 137-144 ◽  
Author(s):  
Xiujun Ren ◽  
Kailian Zhang ◽  
Die Gao ◽  
Qifeng Fu ◽  
Jing Zeng ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Liquid Chromatography ◽  
Stationary Phase ◽  
Mixed Mode ◽  
Sulfonate Group

scholarly journals Mechanism of proton transfer in class A β-lactamase catalysis and inhibition by avibactam

2020 ◽  
Vol 117 (11) ◽  
pp. 5818-5825 ◽  
Author(s):  
Orville A. Pemberton ◽  
Radwan E. Noor ◽  
Vasantha Kumar M. V. ◽  
Ruslan Sanishvili ◽  
M. Trent Kemp ◽  
...  
Keyword(s):  
Proton Transfer ◽  
Critical Role ◽  
Acid Dissociation ◽  
Acid Dissociation Constant ◽  
Sulfonate Group ◽  
Enzyme Complex ◽  
Ultrahigh Resolution ◽  
Catalytic Residues ◽  
Class A ◽  
M 14

Gram-negative bacteria expressing class A β-lactamases pose a serious health threat due to their ability to inactivate all β-lactam antibiotics. The acyl–enzyme intermediate is a central milestone in the hydrolysis reaction catalyzed by these enzymes. However, the protonation states of the catalytic residues in this complex have never been fully analyzed experimentally due to inherent difficulties. To help unravel the ambiguity surrounding class A β-lactamase catalysis, we have used ultrahigh-resolution X-ray crystallography and the recently approved β-lactamase inhibitor avibactam to trap the acyl–enzyme complex of class A β-lactamase CTX-M-14 at varying pHs. A 0.83-Å-resolution CTX-M-14 complex structure at pH 7.9 revealed a neutral state for both Lys73 and Glu166. Furthermore, the avibactam hydroxylamine-O-sulfonate group conformation varied according to pH, and this conformational switch appeared to correspond to a change in the Lys73 protonation state at low pH. In conjunction with computational analyses, our structures suggest that Lys73 has a perturbed acid dissociation constant (pKa) compared with acyl–enzyme complexes with β-lactams, hindering its function to deprotonate Glu166 and the initiation of the deacylation reaction. Further NMR analysis demonstrated Lys73 pKato be ∼5.2 to 5.6. Together with previous ultrahigh-resolution crystal structures, these findings enable us to follow the proton transfer process of the entire acylation reaction and reveal the critical role of Lys73. They also shed light on the stability and reversibility of the avibactam carbamoyl acyl–enzyme complex, highlighting the effect of substrate functional groups in influencing the protonation states of catalytic residues and subsequently the progression of the reaction.

Synthesis of a protein modifying agent. A water-soluble stable free radical

1980 ◽  
Vol 58 (7) ◽  
pp. 714-715 ◽  
Author(s):  
Sangram Sisodia ◽  
R. Dean Martz ◽  
N. Bosworth ◽  
Gary Lammert ◽  
J. D. Reinheimer
Keyword(s):  
Free Radical ◽  
Water Soluble ◽  
Sulfonate Group ◽  
Benzene Sulfonate ◽  
Synthetic Route ◽  
Stable Free Radical ◽  
Sodium Sulfonate ◽  
Modifying Agent ◽  
Synthetic Routes

Two synthetic routes to prepare a water-soluble stable free radical were investigated. The first product, sodium-2,4-dinitro-5-(4′-amino-2′,2′,6′,6′-tetramethylpiperidine-1-oxyl)benzene sulfonate, was water soluble but the sulfonate group was not readily replaceable with nucleophiles. The second synthetic route yielded N(4′-(2′,2′,6′,6′-tetramethylpiperidine-1-oxyl))-3,5-dinitro-4-sodium sulfonate benzamide, which was water soluble and its sulfonate group was readily replaced by nucleophiles.

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