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ortho ‐(Aminomethyl)phenylboronic acids—synthesis, structure and sugar receptor activity
Author(s) -
AdamczykWoźniak Agnieszka,
Brzózka Zbigniew,
Cyrański Michał K.,
FilipowiczSzymańska Alicja,
Klimentowska Paulina,
Żubrowska Anna,
Żukowski Kamil,
Sporzyński Andrzej
Publication year - 2008
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1418
Subject(s) - chemistry , phenylboronic acid , sugar , hydrogen bond , intramolecular force , selectivity , fructose , stereochemistry , galactose , aldose , crystal structure , organic chemistry , molecule , glycoside , catalysis
A series of ortho ‐(aminomethyl)phenylboronic acids was synthesized and their structures were determined by single‐crystal X‐ray diffraction. The structures are stabilized by the inter‐ and intramolecular hydrogen bonds. The sugar‐binding ability of these compounds was evaluated for D ‐glucose, D ‐fructose and D ‐galactose by the competition assay with Alizarin Red S (ARS). The results indicate that the sugar binding ability and selectivity towards sugars depend on the substituents in amino group. Copyright © 2008 John Wiley & Sons, Ltd.