Lewis acidity and sugar receptor activity of 3-amino-substituted benzoxaboroles and their ortho-aminomethylphenylboronic acid analogues

Agnieszka Adamczyk-Woźniak , Krzysztof M. Borys , Izabela D. Madura , Alicja Pawełko , Ewelina Tomecka , Kamil Żukowski

Abstract

The pKas as well as apparent binding constants of several 3-amino-substituted benzoxaboroles with alizarin red S (ARS) and some biologically important sugars have been evaluated and compared with that of the parent aminomethylphenylboronic acids. The investigated benzoxaboroles reveal lower acidity than the corresponding boronic acids. All the studied boronic compounds display the usual order of apparent binding constant values with glucose, galactose and fructose. The X-ray structure of the model catechol ester of the morpholinylmethylphenylboronic acid has been determined. The molecules are monomeric zwitterions with a tetracoordinated boron atom. The intermolecular interactions have been described with the aid of the Hirshfeld surface analysis.
Author Agnieszka Adamczyk-Woźniak (FC / DPC)
Agnieszka Adamczyk-Woźniak,,
- Department Of Physical Chemistry
, Krzysztof M. Borys (FC / DPC)
Krzysztof M. Borys,,
- Department Of Physical Chemistry
, Izabela D. Madura (FC / CICSST)
Izabela D. Madura,,
- Chair Of Inorganic Chemistry And Solid State Technology
, Alicja Pawełko (FC / DPC)
Alicja Pawełko,,
- Department Of Physical Chemistry
, Ewelina Tomecka (FC / IBC / DM)
Ewelina Tomecka,,
- Department Of Microbioanalytics
, Kamil Żukowski (FC / IBC / DM)
Kamil Żukowski,,
- Department Of Microbioanalytics
Journal seriesNew Journal of Chemistry, ISSN 1144-0546
Issue year2013
Vol37
No1
Pages188-194
Publication size in sheets0.5
ASJC Classification2505 Materials Chemistry; 1600 General Chemistry; 1503 Catalysis
DOIDOI:10.1039/c2nj40687j
URL http://pubs.rsc.org/en/content/articlelanding/2013/nj/c2nj40687j#!divAbstract
Languageen angielski
File
newjournalofchemistry_2013_37_188.pdf 1.87 MB
Score (nominal)30
Score sourcejournalList
ScoreMinisterial score = 30.0, 26-06-2020, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 26-06-2020, ArticleFromJournal
Publication indicators Scopus Citations = 31; WoS Citations = 28; GS Citations = 17.0; Scopus SNIP (Source Normalised Impact per Paper): 2014 = 0.872; WoS Impact Factor: 2013 = 3.159 (2) - 2013=2.837 (5)
Citation count*17 (2016-06-01)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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