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Optimized one-pot derivatization and enantioseparation of cysteine: Application to the study of a dietary supplement

Saluti, Giorgio
Galarini, Roberta
Carotti, Andrea
Macchiarulo, Antonio
Sardella, Roccaldo
Published in Journal of Pharmaceutical and Biomedical Analysis. 2020, vol. 180, p. 113066
Abstract Cysteine is a sulfur-containing amino acid which plays an outstanding role in many biological pathways in mammals. The analysis and quantification of native cysteine remains a critical issue due to its highly reactive thiol group evolving to the disulfide cystine derivative through oxidation reaction. Aimed at improving the derivative stability, cysteine was labelled with 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F), which reacts with both amino and thiol groups. The derivatization was optimized and the chemical identity of the reaction product was assessed via high-resolution mass spectrometry. The NBD-cysteine derivative resulted stable for 10 days. This derivative was enantioresolved (α and RS equal to 1.25 and 2.70, respectively) thanks to a (R,R)-Whelk-O1 phase with the following chromatographic setting: eluent, MeOH/water-90/10 (v/v) with 15 mM ammonium formate ( 6.0); column temperature, 35 °C; flow rate, 1.0 mL/min. The developed method was validated following the ICH guidelines and applied for the quality control of a L-cysteine containing dietary supplement.
Keywords Cysteine derivativeDietary supplementEnantioselective liquid chromatographyMethod validationOptimized derivatization processa
PMID: 31891875
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Research group Sciences analytiques
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PUCCIARINI, Lucia et al. Optimized one-pot derivatization and enantioseparation of cysteine: Application to the study of a dietary supplement. In: Journal of Pharmaceutical and Biomedical Analysis, 2020, vol. 180, p. 113066. doi: 10.1016/j.jpba.2019.113066 https://archive-ouverte.unige.ch/unige:133087

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Deposited on : 2020-03-25

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