Issue 5, 2010
From the journal:

Organic & Biomolecular Chemistry

A fluorescent diastereoselective molecular sensor for 1,2-aminoalcohols based on the rhodamine B lactone–zwitterion equilibrium

Clifton J. Stephensona  and  Ken D. Shimizu*b  

* Corresponding authors

a Carthage College, Kenosha, WI, USA
E-mail: cstephenson@carthage.edu
Fax: +1 262 551 6208
Tel: +1 262 551 6327

b Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC, USA
E-mail: shimizu@mail.chem.sc.edu
Fax: +1 803 777 9521
Tel: +1 803 777 6523

Abstract

A simple yet highly sensitive diastereoselective fluorescent assay was developed, which can differentiate diastereomeric 1,2-aminoalcohols such as ephedrine, pseudoephedrine, and methylephedrine using commercially available xanthene dyes. The assay is based on the rhodamine B lactone–zwitterion equilibrium, which is highly sensitive to the presence and structure of 1,2-aminoalcohols. This is in contrast to the majority of rhodamine sensors, which are based on the pH sensitive carboxylate–lactone equilibrium. A model is proposed in which the diastereoselectivity arises from the differences in the strength of an intermolecular lone pair-π interaction within the analyte–rhodamine zwitterion complex. An assay was developed based on this sensing mechanism in which the structure and concentration of a 1,2-aminoalcohol solution can be determined using a mixture of rhodamine B and fluorescein. The selectivity and accuracy of this two-dye system was then demonstrated by the ability to measure the diastereomeric excess of samples of methylephedrine with 98% accuracy.

Graphical abstract: A fluorescent diastereoselective molecular sensor for 1,2-aminoalcohols based on the rhodamine B lactone–zwitterion equilibrium

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Article information

DOI
https://doi.org/10.1039/B918823A
Article type
Paper
Submitted
21 Sep 2009
Accepted
05 Dec 2009
First published
07 Jan 2010

Org. Biomol. Chem., 2010,8, 1027-1032

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A fluorescent diastereoselective molecular sensor for 1,2-aminoalcohols based on the rhodamine B lactone–zwitterion equilibrium

C. J. Stephenson and K. D. Shimizu, Org. Biomol. Chem., 2010, 8, 1027 DOI: 10.1039/B918823A

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