Issue 7, 2021

A rapid and sensitive method for chiroptical sensing of α-amino acids via click-like labeling with o-phthalaldehyde and p-toluenethiol

Abstract

A highly practical method for comprehensive chiroptical sensing of free α amino acids with streamlined operation and high sensitivity via dual CD/UV measurements is developed. The assay takes advantage of an efficient and selective three-component labeling reaction of primary amines with o-phthalaldehyde and p-toluenethiol reagents to derivatize the NH2 group of analytes into an isoindole. The covalent labeling generates sensitive UV and CD readouts, both of which show an excellent linear relationship with the concentration of analytes. The high reactivity and the novel optical reporting mechanism allow fast and accurate measurement without background interference. The sensing assay works well for a remarkably broad range of analyte concentrations, with an unprecedented lower limit of 10 micromolar concentration.

Graphical abstract: A rapid and sensitive method for chiroptical sensing of α-amino acids via click-like labeling with o-phthalaldehyde and p-toluenethiol

Supplementary files

Article information

Article type
Edge Article
Submitted
18 10 2020
Accepted
18 12 2020
First published
22 12 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 2504-2508

A rapid and sensitive method for chiroptical sensing of α-amino acids via click-like labeling with o-phthalaldehyde and p-toluenethiol

B. Li, J. Zhang, L. Li and G. Chen, Chem. Sci., 2021, 12, 2504 DOI: 10.1039/D0SC05749E

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