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Factors affecting the affinity of boronic acid derivatives to linear polyols: The substituents of boronic acid derivatives and relative position of dihydroxyl group in polyols.

Authors :
Meng, Qiyu
Wang, Yupei
Rong, Meng
Xing, Huifang
Yang, Liangrong
Liu, Huizhou
Chi, Ru-An
Chen, Congmei
Source :
Separation & Purification Technology. Jul2024, Vol. 340, pN.PAG-N.PAG. 1p.
Publication Year :
2024

Abstract

• Binding constant and thermodynamic data of phenylboronic acid derivates and structurally similar linear polyols were investigated through three methods. • The numbers and relative positions of the dihydroxyl group in polyols affected the affinity of the boronic acid group to it. • Intermolecular hydrogen bonding improved the thermodynamic stability of phenylboronate. The separation of 1,2,4-butanetriol (BT) through phenylboronate anion reactive extraction in fermentation broth has been proposed based on the process where the boronic acid groups specifically recognize the cis -dihydroxyl groups. To fully elucidate the affinity process of boronic acid group and polyols, here we have investigated the binding constant (K a) and thermodynamic data of four phenylboronic acid derivates (PBADs) and four structurally similar linear polyols (BT, 1,2-butanediol (1,2-BD), 1,3-butanediol (1,3-BD), and 1,4-butanediol (1,4-BD)) through fluorescence spectroscopy, isothermal titration calorimetry (ITC), and computational chemistry. It can be concluded that the substituent group of boronic acid, the numbers and relative positions of the hydroxyl group in polyols affected the affinity of the boronic acid group to it. The ionized boronic acid group preferentially reacts with the 1,2-dihydroxy group to form a pentacyclic phenylboronate. Compared with other three butanediols, phenylboronic acid (PBA) has a larger binding constant and shows a smaller Gibbs free energy change with BT. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
13835866
Volume :
340
Database :
Academic Search Index
Journal :
Separation & Purification Technology
Publication Type :
Academic Journal
Accession number :
176809682
Full Text :
https://doi.org/10.1016/j.seppur.2024.126698