Issue 2, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Design, synthesis and structure of new potential electrochemically active boronic acid-based glucose sensors†

Jens Chr. Norrild‡*a  and  Inger Søtofteb  

* Corresponding authors

a University of Copenhagen, Department of Chemistry, Laboratory for General and Organic Chemistry, Universitetsparken 5, DK-2100 Copenhagen, Denmark
E-mail: jcn@torsanadd.com

b Technical University of Denmark, Department of Chemistry, DK-2800 Kgs.Lyngby, Denmark
E-mail: is@kemi.dtu.dk
Fax: +45 45 88 31 36

Abstract

In the course of our investigations on new boronic acid based carbohydrate sensors three new boronic acids 3, 7 and 11 containing a ferrocene moiety were synthesised. Their design includes an intramolecular B–N bonding motif in order to facilitate binding at physiological pH. We report the synthesis of the compounds and our investigations on glucose complexation as studied by 13C NMR spectroscopy. The crystal structure of 2,4,6-tris[2-(N-ferrocenylmethyl-N-methylaminomethyl)phenyl]boroxin (13) (boroxin of boronic acid 3) (boroxin = cyclotriboroxane) was obtained and compared with structures obtained of 2,4,6-tris[2-(N,N-dimethylaminomethyl)phenyl]boroxin (14) and 2,2-dimethyl-1,3-diyl[2-(N,N-dimethylaminomethyl)phenyl]boronate (15). The structure of 13 shows the existence of intramolecular B–N bonds in the solid phase.

Graphical abstract: Design, synthesis and structure of new potential electrochemically active boronic acid-based glucose sensors

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Article information

DOI
https://doi.org/10.1039/B107457A
Article type
Paper
Submitted
17 Aug 2001
Accepted
12 Nov 2001
First published
10 Jan 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 303-311

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Design, synthesis and structure of new potential electrochemically active boronic acid-based glucose sensors

J. Chr. Norrild and I. Søtofte, J. Chem. Soc., Perkin Trans. 2, 2002, 303 DOI: 10.1039/B107457A

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