Detailed Reaction Mechanism of Bis-(o-Aminomethylphenylboronic Acid)-based Receptors with Various Length Methylene-chain Linkers with D-Glucose

Yuki Ohno, Rei Tanaka, Yota Suzuki, Tomoaki Sugaya, Satoshi Iwatsuki, Masahiko Inamo, Koji Ishihara*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The detailed reaction mechanisms of several bis-(o-aminomethylphenylboronic acid)-based receptors, linked with methylene chains of different lengths (i. e., DBAn (n=2, 3, and 4) having 2n methylene groups), with D-glucose were kinetically investigated in methanolic aqueous solutions. The pKa measurements showed that the two boronic acid moieties in DBAn were equivalent and had no electronic interaction between them. DBA2 reacted with D-glucose to form a 1 : 1 product, in which two boronic acid moieties in one molecule of DBA2 were bound to two reactive sites in one molecule of D-glucose. DBA3 and DBA4 reacted with D-glucose to form a 1 : 2 product, in which the two boronic acid moieties in one molecule of DBA3 or DBA4 were bound to two molecules of D-glucose simultaneously through one reactive site. Thus, in the recognition of D-glucose, the distance between the two boronic acid moieties in DBAn was optimal for n=2 and too long for n=3 or 4.

Original languageEnglish
Article numbere202200603
JournalChemistrySelect
Volume7
Issue number29
DOIs
Publication statusPublished - 2022 Aug 5

Keywords

  • bis-(o-aminomethylphenylboronic acid)
  • boron
  • D-glucose
  • diboronic acid
  • kinetics
  • reaction mechanism

ASJC Scopus subject areas

  • Chemistry(all)

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