Simultaneous analysis of amino acids based on discriminative 19F NMR spectroscopy

Biling Huang; Lihua Xu; Zhao Zhao; Ning Wang; Yufen Zhao; Shaohua Huang

doi:10.1016/j.bioorg.2022.105818

Simultaneous analysis of amino acids based on discriminative ¹⁹F NMR spectroscopy

Bioorg Chem. 2022 Jul:124:105818. doi: 10.1016/j.bioorg.2022.105818. Epub 2022 Apr 26.

Authors

Biling Huang¹, Lihua Xu², Zhao Zhao², Ning Wang³, Yufen Zhao⁴, Shaohua Huang⁵

Affiliations

¹ Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, PR China; Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo, Zhejiang, PR China. Electronic address: huangbiling@nbu.edu.cn.
² Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, PR China.
³ Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, PR China; Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo, Zhejiang, PR China.
⁴ Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, PR China; Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo, Zhejiang, PR China; Department of Chemical Biology, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen 361005, PR China; Key Lab of Bioorganic Phosphorus Chemistry & Chemical Biology, Department of Chemistry, Tsinghua University, Beijing 100084, PR China.
⁵ Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, PR China; Qian Xuesen Collaborative Research Center of Astrochemistry and Space Life Sciences, Ningbo University, Ningbo, Zhejiang, PR China. Electronic address: huangshaohua@nbu.edu.cn.

PMID: 35489271
DOI: 10.1016/j.bioorg.2022.105818

Abstract

The simultaneous analysis of amino acids (AAs) is crucial for human health, diagnosis and treatment of disease, and nutritional quality evaluation in foodstuffs. Here, we establish an easy and rapid method for the simultaneous analysis of AAs using a single reagent 2-(trifluoromethyl)benzaldehyde (oTFMBA) based on spectral-separation-enabled ¹⁹F NMR spectroscopy. oTFMBA, a highly sensitive chemosensor, is capable of analyzing 19 proteinogenic AAs or non-amino acid amines (non-AAs) in a complex mixture by adjusting the pH in a toilless way. The ¹⁹F signals of oTFMBA-labeled AAs are distributed over a wide range of ∼ 0.7 ppm, demonstrating oTFMBA with higher resolution for simultaneous analysis of AAs compared to the o-phthaldialdehyde (OPA) method (<0.6 ppm). Additionally, 12 AAs were unambiguously identified in human urine, including Asp, Ser, Gly, Thr, Glu, Arg, Ala, Val, Ile, Tyr, His, and Phe. Furthermore, our method's detection limit for AAs is 5.83 μM, illustrating sensitivity with an ∼100-fold improvement over the OPA method. This work represents an approach to the analysis of AAs or non-AAs in a complicated mixture (even biofluid) using a ¹⁹F NMR probe with high sensitivity, which is of great significance for the simultaneous analysis of multiple analytes.

Keywords: (19)F probe; Amino acids; Chemosensor; NMR; Simultaneous analysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines
Amino Acid Sequence
Amino Acids*
Humans
Magnetic Resonance Spectroscopy
Peptide Fragments*
Trypsin

Substances

Amines
Amino Acids
Peptide Fragments
Trypsin