Photo-responsive host–guest complexation directs dynamic covalent condensation of phenyl boronic acid and d-fructose

2021 ◽  
Author(s):  
Florian Klepel ◽  
Bart Jan Ravoo
Keyword(s):  
Boronic Acid ◽  
Covalent Interaction ◽  
Phenyl Boronic Acid

The photo-responsive host-guest interaction of an azo-based photoswitch with permethylated cyclodextrin is used to modulate the dynamic covalent interaction of a phenyl boronic acid and D-fructose by irradiation with light.

Arylboronic Acids in Self-condensation of Glucosamines Forming Deoxyfructosazine, Catalysts or Reagents?

2019 ◽  
Author(s):  
Meifeng Wang ◽  
Gan Zhu ◽  
Yiqun Li ◽  
Liuqun Gu
Keyword(s):  
Molecular Recognition ◽  
Boric Acid ◽  
Boronic Acid ◽  
Catalytic Mechanism ◽  
Organic Transformations ◽  
Food Industries ◽  
Arylboronic Acids ◽  
Excess Amount ◽  
Phenyl Boronic Acid ◽  
Boron Acid

Arylboronic acids were widely used as efficient catalysts in direct amide formation and other organic transformations. Surprisingly, reports on their use as catalysts in carbohydrates synthesis are very rare even though boron acid-diol complexation was extensively investigated in molecular recognition for saccharides and so on. Here we developed an efficient arylboronic acids catalyzed dimerization of glucosamines forming deoxyfructosazine which is important compound in pharmaceutical and food industries, against a commonly held belief that excess amount of phenyl boronic acid (or boric acid) is a must. A catalytic mechanism was also proposed and arylboronic acids instead of their boronates was identified as catalysts.

scholarly journals Analysis of glycoproteins by SDS-PAGE with methacrylamido phenyl boronic acid

2014 ◽  
Vol 58 (2) ◽  
pp. 33-35 ◽  
Author(s):  
Yuichi Aikyo ◽  
Masamichi Oh-Ishi
Keyword(s):  
Boronic Acid ◽  
Sds Page ◽  
Phenyl Boronic Acid

scholarly journals Crystal Structures of KPC-2 β-Lactamase in Complex with 3-Nitrophenyl Boronic Acid and the Penam Sulfone PSR-3-226

2012 ◽  
Vol 56 (5) ◽  
pp. 2713-2718 ◽  
Author(s):  
Wei Ke ◽  
Christopher R. Bethel ◽  
Krisztina M. Papp-Wallace ◽  
Sundar Ram Reddy Pagadala ◽  
Micheal Nottingham ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Active Site ◽  
Boronic Acid ◽  
Carbonyl Oxygen ◽  
Oxyanion Hole ◽  
Covalent Interaction ◽  
Class A ◽  
Inactivation Rate Constant ◽  
Reversible Covalent ◽  
Acid Compound

ABSTRACTClass A carbapenemases are a major threat to the potency of carbapenem antibiotics. A widespread carbapenemase, KPC-2, is not easily inhibited by β-lactamase inhibitors (i.e., clavulanic acid, sulbactam, and tazobactam). To explore different mechanisms of inhibition of KPC-2, we determined the crystal structures of KPC-2 with two β-lactamase inhibitors that follow different inactivation pathways and kinetics. The first complex is that of a small boronic acid compound, 3-nitrophenyl boronic acid (3-NPBA), bound to KPC-2 with 1.62-Å resolution. 3-NPBA demonstrated aKmvalue of 1.0 ± 0.1 μM (mean ± standard error) for KPC-2 and blocks the active site by making a reversible covalent interaction with the catalytic S70 residue. The two boron hydroxyl atoms of 3-NPBA are positioned in the oxyanion hole and the deacylation water pocket, respectively. In addition, the aromatic ring of 3-NPBA provides an edge-to-face interaction with W105 in the active site. The structure of KPC-2 with the penam sulfone PSR-3-226 was determined at 1.26-Å resolution. PSR-3-226 displayed aKmvalue of 3.8 ± 0.4 μM for KPC-2, and the inactivation rate constant (kinact) was 0.034 ± 0.003 s−1. When covalently bound to S70, PSR-3-226 forms atrans-enamine intermediate in the KPC-2 active site. The predominant active site interactions are generated via the carbonyl oxygen, which resides in the oxyanion hole, and the carboxyl moiety of PSR-3-226, which interacts with N132, N170, and E166. 3-NPBA and PSR-3-226 are the first β-lactamase inhibitors to be trapped as an acyl-enzyme complex with KPC-2. The structural and inhibitory insights gained here could aid in the design of potent KPC-2 inhibitors.

On the sensitivity of alginate rheology to composition

Soft Matter ◽  
2019 ◽  
Vol 15 (2) ◽  
pp. 159-165 ◽  
Author(s):  
Karthika Suresh ◽  
Marleen Häring ◽  
Guruswamy Kumaraswamy ◽  
David Díaz Díaz
Keyword(s):  
Viscoelastic Fluid ◽  
Boronic Acid ◽  
Linear Response ◽  
High Strain ◽  
Strain Behaviour ◽  
Phenyl Boronic Acid ◽  
Universal Composition

The linear response of alginate-phenyl boronic acid (Alg-PBA) esters shows a universal, composition-independent viscoelastic fluid-like behaviour. However, their high strain behaviour is very sensitive to composition.

Suzuki-Coupling of Cp*Ru(para-C6H4Br2) with Phenyl Boronic Acid: A Model Reaction for the Synthesis of Organometallic Polymers

1996 ◽  
Vol 129 (11) ◽  
pp. 1323-1325 ◽  
Author(s):  
Kathrin Harre ◽  
Volker Enkelmann ◽  
Margit Schulze ◽  
Uwe H. F. Bunz
Keyword(s):  
Boronic Acid ◽  
Suzuki Coupling ◽  
Model Reaction ◽  
Organometallic Polymers ◽  
Phenyl Boronic Acid

Anionic chromogenic chemosensors highly selective for cyanide based on the interaction of phenyl boronic acid and solvatochromic dyes

2015 ◽  
Vol 221 ◽  
pp. 644-652 ◽  
Author(s):  
Lizandra Maria Zimmermann ◽  
Jaqueline Nicolini ◽  
Vanderléia Gava Marini ◽  
Vanderlei Gageiro Machado
Keyword(s):  
Boronic Acid ◽  
Solvatochromic Dyes ◽  
Phenyl Boronic Acid
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