Deprotection of Pinacolyl Boronate Esters by Transesterification with Polystyrene—Boronic Acid.

ChemInform ◽  
2004 ◽  
Vol 35 (49) ◽  
Author(s):  
Thomas E. Pennington ◽  
Cynantya Kardiman ◽  
Craig A. Hutton
Keyword(s):  
Boronic Acid ◽  
Boronate Esters

Deprotection of pinacolyl boronate esters by transesterification with polystyrene–boronic acid

2004 ◽  
Vol 45 (35) ◽  
pp. 6657-6660 ◽  
Author(s):  
Thomas E. Pennington ◽  
Cynantya Kardiman ◽  
Craig A. Hutton
Keyword(s):  
Boronic Acid ◽  
Boronate Esters

Immobilisation and stabilisation of glycosylated enzymes on boronic acid-functionalised silica nanoparticles

2021 ◽  
Author(s):  
Seyed Amirabbas Nazemi ◽  
Magdalena Olesińska ◽  
Cinzia Pezzella ◽  
Simona Varriale ◽  
Chia-Wei Lin ◽  
...  
Keyword(s):  
Silica Nanoparticles ◽  
Boronic Acid ◽  
Boronate Esters ◽  
Enzyme Immobilisation

We report a method of glycosylated enzyme immobilisation and stabilisation based on the formation of boronate esters between a surface-attached boronate and the enzyme glycans, followed by the growth of an organosilica layer of controlled thickness.

The Structural Basis for Hydrolysis Resistance in the Esters of (2-Formylphenyl)boronic Acid 2,4-Dinitrophenylhydrazones

2002 ◽  
Vol 67 (7) ◽  
pp. 1084-1094 ◽  
Author(s):  
Michael P. Groziak ◽  
Paul D. Robinson
Keyword(s):  
Boronic Acid ◽  
Intramolecular Interaction ◽  
Boronic Acids ◽  
Membered Ring ◽  
Structural Basis ◽  
Previous Suggestion ◽  
Boronate Esters ◽  
X Ray ◽  
Hydrolysis Resistance ◽  
Electron Deficiency

Under conditions that typically afford bicyclic boron heterocycles directly, (2-formylphenyl)boronic acids react with 2,4-dinitrophenylhydrazine in ethanol to give highly waterresistant diethyl boronate esters. Two such 2,4-dinitrophenylhydrazones were prepared and their X-ray crystal structures determined. Contrary to a previous suggestion that their unusual stability is due to an intramolecular N→B coordination giving a six-membered BN2C3 ring system based on a (Z)-hydrazone, these compounds instead were found to be (E)-hydrazones internally stabilized by a weak intramolecular interaction between nitrogen and boron from within a five-membered ring. Further study revealed that the electron deficiency of the starting hydrazine reagent plays a key role in determining the structure of the hydrazone isolated, and that the water-resistant boronate esters can be hydrolyzed under forcing conditions to the boronic acids.

scholarly journals Gelating Abilities of Two-Component System of Catecholic Derivatives and a Boronic Acid

Gels ◽  
2019 ◽  
Vol 5 (4) ◽  
pp. 45 ◽  
Author(s):  
Akihiko Tsuge ◽  
Ryota Kamoto ◽  
Daisuke Yakeya ◽  
Koji Araki
Keyword(s):  
Boronic Acid ◽  
Noncovalent Interactions ◽  
Three Dimensional ◽  
Two Component System ◽  
Boronate Esters ◽  
Component System ◽  
Practical Applications ◽  
Unit Form ◽  
Two Component ◽  
Low Molecular Weight Organogelators

In the last two decades, various kinds of the low-molecular-weight organogelators (LMOGs) have been investigated in terms of technological applications in various fields as well as their fundamental scientific properties. The process of gelation is generally considered to arise from immobilization of the solvents in the three-dimensional networks formed by the assembly of gelator molecules through weak intermolecular noncovalent interactions. From these points of view a huge number of organogelators have been developed so far. In the course of our research on LMOGs we have noticed a mixture of two gelators could show a different trend in gelation compared to the single gelator. It is well known that the catecholic moiety easily forms cyclic boronate esters with the boronic acid. Thus, we have investigated the two-component system based on cyclic boronate esters formed by the catechols and a boronic acid in terms of the control of gelation capability. Basic gelation properties of the constituent catecholic gelators have also been clarified. The catecholic gelators with the amide unit form no gel by addition of the boronic acid. In contrast, the catecholic gelators with the glutamic acid moiety improve their gelation abilities by mixing with the boronic acid. Furthermore, the gelation ability of the catecholic gelators having the urea unit is maintained after addition of the boronic acid. It has been found that gelation abilities of the catecholic gelators are highly affected by addition of the boronic acid. In terms of practical applications some gels can be obtained by on-site mixture of two kinds of solutions.

Examination of pinanediol–boronic acid ester formation in aqueous media: relevance to the relative stability of trigonal and tetrahedral boronate esters

2020 ◽  
Vol 18 (14) ◽  
pp. 2716-2726
Author(s):  
Mayte A. Martínez-Aguirre ◽  
Marcos Flores-Alamo ◽  
Felipe Medrano ◽  
Anatoly K. Yatsimirsky
Keyword(s):  
Boronic Acid ◽  
Relative Stability ◽  
Acid Ester ◽  
Aqueous Media ◽  
Boronate Esters ◽  
Inverted Order ◽  
Ester Formation ◽  
Strain Release ◽  
Diol Ester

The “inverted” order of stabilities Ktrig > Ktet is observed for pinanediol boronate esters in spite of the existence of the usual strain release effect in the O–B–O angle of the cyclic diol ester.

A Boronic Acid-Based Fluorescence Hydrogel for Monosaccharide Detection

2018 ◽  
Author(s):  
Suying Xu ◽  
Adam Sedgwick ◽  
Souad Elfecky ◽  
Wenbo Chen ◽  
Ashley Jones ◽  
...  
Keyword(s):  
Fluorescent Probe ◽  
Boronic Acid ◽  
Binding Constants ◽  
Strong Fluorescence ◽  
Fluorescence Response ◽  
Turn On ◽  
Fluorescence Turn On ◽  
Hydrogel System

<p>A boronic acid-based anthracene fluorescent probe was functionalised with an acrylamide unit to incorporate into a hydrogel system for monosaccharide detection<i>. </i>In solution, the fluorescent probe<b> </b>displayed a strong fluorescence turn-on response upon exposure to fructose, and an expected trend in apparent binding constants, as judged by a fluorescence response where D-fructose > D-galactose > D-mannose > D-glucose. The hydrogel incorporating the boronic acid monomer demonstrated the ability to detect monosaccharides by fluorescence with the same overall trend as the monomer in solution with the addition of fructose resulting in a 10-fold enhancement (≤ 0.25 M). <b><u></u></b></p>

Theoretical Studies of the Acid-Base Equilibria in a Model Active Site of the Human 20S Proteasome

2020 ◽  
Author(s):  
Jon Uranga ◽  
Lukas Hasecke ◽  
Jonny Proppe ◽  
Jan Fingerhut ◽  
Ricardo A. Mata
Keyword(s):  
Active Site ◽  
Boronic Acid ◽  
Computational Study ◽  
Ubiquitin Proteasome System ◽  
Bayesian Optimization ◽  
Inhibition Mechanism ◽  
20S Proteasome ◽  
Acid Base ◽  
Ubiquitin Proteasome ◽  
Infection Cycles

The 20S Proteasome is a macromolecule responsible for the chemical step in the ubiquitin-proteasome system of degrading unnecessary and unused proteins of the cell. It plays a central role both in the rapid growth of cancer cells as well as in viral infection cycles. Herein, we present a computational study of the acid-base equilibria in an active site of the human proteasome, an aspect which is often neglected despite the crucial role protons play in the catalysis. As example substrates, we take the inhibition by epoxy and boronic acid containing warheads. We have combined cluster quantum mechanical calculations, replica exchange molecular dynamics and Bayesian optimization of non-bonded potential terms in the inhibitors. In relation to the latter, we propose an easily scalable approach to the reevaluation of non-bonded potentials making use of QM/MM dynamics information. Our results show that coupled acid-base equilibria need to be considered when modeling the inhibition mechanism. The coupling between a neighboring lysine and the reacting threonine is not affected by the presence of the inhibitor.

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.

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