Determination of Enantiomeric Excess by Solid-Phase Extraction Using a Chiral Metal-Organic Framework as Sorbent.

Jun-Hui Zhang,Xing-Lian Chen,Bang-Jin Wang,Bo Tang,Min Zi,Sheng-Ming Xie,Mei Zhang,Li-Ming Yuan

doi:10.3390/molecules23112802

Abstract

Metal-organic frameworks (MOFs) have recently attracted considerable attention because of their fascinating structures and intriguing potential applications in diverse areas. In this study, we developed a novel method for determination of enantiomeric excess (ee) of (±)-1,1′-bi-2-naphthol by solid-phase extraction (SPE) using a chiral MOF, [Co(l-tyr)]n(l-tyrCo), as sorbent. After optimization of the experimental conditions, a good linear relationship between the ee and the absorbance of the eluate (R2 = 0.9984) was obtained and the standard curve was established at the concentration of 3 mmol L−1. The ee values of (±)-1,1′-bi-2-naphthol samples can be rapidly calculated using the standard curve after determination of the absorbance of the eluate. The method showed good accuracy, with an average error of 2.26%, and is promising for ee analysis.

Highlights

Optical purity is important in many industries, in the development and production of pharmaceuticals
All chemicals and reagents used in this study were at least of analytical grade
Co(CH3 COO)2 ·4H2 O, L-tyrosine, and NaOH were purchased from Adamas-beta (Shanghai, China), and were used for the synthesis of Metal-organic frameworks (MOFs), [Co(L-tyr)]n (L-tyrCo)

Summary

Introduction

Optical purity is important in many industries, in the development and production of pharmaceuticals. The determination of enantiomeric excess (ee) of chiral compounds is very important. Chiral chromatographic methods, such as high performance liquid chromatography (HPLC) and gas chromatography (GC) using chiral stationary phases (CSPs), are most commonly used to determine ee values. These methods have some drawbacks, such as the high cost of chiral columns and long analysis times. The development of simple and fast methods for ee analysis has great value. A number of techniques for rapid ee analysis have been developed, including circular dichroism [2,3], UV and colorimetric methods [4,5], fluorescence spectroscopy [6,7], mass spectrometry [8], and molecularly imprinted polymer based assays [9]

Methods

Results

Conclusion