A cyclodextrin-based reagent for cis/trans-geometrical isomers separation by mobility measurements and chemical calculations

Fangling Wu; Xishi Wu; Zhe Li; Di Zhang; Chuan-Fan Ding

doi:10.1016/j.foodchem.2022.135027

A cyclodextrin-based reagent for cis/trans-geometrical isomers separation by mobility measurements and chemical calculations

Food Chem. 2023 Apr 16:406:135027. doi: 10.1016/j.foodchem.2022.135027. Epub 2022 Nov 29.

Authors

Fangling Wu¹, Xishi Wu², Zhe Li³, Di Zhang⁴, Chuan-Fan Ding⁵

Affiliations

¹ Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, China. Electronic address: wufangling@nbu.edu.cn.
² Engineering Laboratory of Advanced Energy Materials, Ningbo Institute of Materials Technology& Engineering, Chinese Academy of Sciences, Ningbo, Zhejiang 315201, China.
³ Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, China.
⁴ Center for Advanced Measurement Science, National Institute of Metrology, Beijing 100084, China. Electronic address: zhangdi@fudan.edu.cn.
⁵ Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, Institute of Mass Spectrometry, School of Material Science and Chemical Engineering, Ningbo University, Ningbo, Zhejiang 315211, China. Electronic address: dingchuanfan@nbu.edu.cn.

PMID: 36493573
DOI: 10.1016/j.foodchem.2022.135027

Abstract

Identification of cis/trans-carbon-carbon double-bond (CC) isomers remain challenging. Herein, a simple and rapid method for the separation and analysis of cis/trans-maleic acid (MA) and aconitic acid (AA) using Trapped Ion Mobility Spectrometry (TIMS) was developed. α-, β-, γ-cyclodextrin (CD) were served as the separation reagent, slight difference in mobility separation was obtained by [CD-MA/AA-H]^-. Specially, with the addition of divalent metal ion (G²⁺) as coordination metal ion, the separation effect was much increased by [CD-MA/AA + G-H]⁺, and α-CD has better mobility separation effect than β-/γ-CD. Moreover, chemical calculations revealed the binary and ternary complexes are in the inclusion forms, and microscopic interactions between cis/trans-MA/AA, CDs, and G²⁺ are somewhat different that making their mobility separation. Finally, quantifications of cis/trans-isomers were analyzed in food samples, with good linearity (R² > 0.99) and recoveries obtained from 87.25 % to 100.73 %.

Keywords: Chemical calculations; Cis-/trans-geometrical isomers; Cyclodextrin; Divalent metal ion; Mobility separation.

MeSH terms

Cyclodextrins* / chemistry
Isomerism

Substances

Cyclodextrins