Development of a diphenyl sulfide structure derivatization reagent for amino acid enantiomers analysis : Application of dynamic monitoring in human urine after drinking wine
Copyright © 2022 Elsevier B.V. All rights reserved..
We developed a novel chiral mass spectrometry derivatization reagent (S)-(3-(4-carboxythiazolidin-3-yl)-3-oxopropyl) diphenylsulfonium (CTOD) with a positively charged sulfur-containing structure for high-sensitivity detection of the chiral resolution of amino acid enantiomers. CTOD reacted with DL-amino acids at 60oC for 60 min to generate the corresponding diastereomers, fifteen chiral amino acid-derived products were separated. Resolution (Rs) values were of the range 1.54-4.36, except Asn 1.07, achieving good separation. A highly sensitive and selective UHPLC-MS/MS method for the simultaneous determination and chiral separation of five chiral amino acids (Pro, Ala, Glu, Asp, and Phe) based on CTOD derivatization was established and applied to the detection of chiral amino acids in different wines. The diastereomeric resolution of the five amino acids was 1.71-5.42, and an excellent linear relationship was obtained in the range of 0.25-500 pmol (R2 ≥0.9993). The detection limit was 0.05-0.25 pmol. The intra- and inter-day precisions were 0.51-5.76% and 0.78-5.18%, respectively, and the average recovery was 90.03-99.99%. In addition, the metabolic concentration of chiral amino acids was monitored after drinking red wine and white wine, and the fitting curve of metabolic concentration was drawn.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2023 |
|---|---|
| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:1688 |
|---|---|
| Enthalten in: |
Journal of chromatography. A - 1688(2023) vom: 11. Jan., Seite 463698 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Di, Lei [VerfasserIn] |
|---|
| Links: |
|---|
| Themen: |
Amines |
|---|
| Anmerkungen: |
Date Completed 03.01.2023 Date Revised 03.01.2023 published: Print-Electronic Citation Status MEDLINE |
|---|
| doi: |
10.1016/j.chroma.2022.463698 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM350407355 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM350407355 | ||
| 003 | DE-627 | ||
| 005 | 20231226044922.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231226s2023 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1016/j.chroma.2022.463698 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n1167.xml |
| 035 | |a (DE-627)NLM350407355 | ||
| 035 | |a (NLM)36528900 | ||
| 035 | |a (PII)S0021-9673(22)00889-5 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Di, Lei |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Development of a diphenyl sulfide structure derivatization reagent for amino acid enantiomers analysis |b Application of dynamic monitoring in human urine after drinking wine |
| 264 | 1 | |c 2023 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 03.01.2023 | ||
| 500 | |a Date Revised 03.01.2023 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2022 Elsevier B.V. All rights reserved. | ||
| 520 | |a We developed a novel chiral mass spectrometry derivatization reagent (S)-(3-(4-carboxythiazolidin-3-yl)-3-oxopropyl) diphenylsulfonium (CTOD) with a positively charged sulfur-containing structure for high-sensitivity detection of the chiral resolution of amino acid enantiomers. CTOD reacted with DL-amino acids at 60oC for 60 min to generate the corresponding diastereomers, fifteen chiral amino acid-derived products were separated. Resolution (Rs) values were of the range 1.54-4.36, except Asn 1.07, achieving good separation. A highly sensitive and selective UHPLC-MS/MS method for the simultaneous determination and chiral separation of five chiral amino acids (Pro, Ala, Glu, Asp, and Phe) based on CTOD derivatization was established and applied to the detection of chiral amino acids in different wines. The diastereomeric resolution of the five amino acids was 1.71-5.42, and an excellent linear relationship was obtained in the range of 0.25-500 pmol (R2 ≥0.9993). The detection limit was 0.05-0.25 pmol. The intra- and inter-day precisions were 0.51-5.76% and 0.78-5.18%, respectively, and the average recovery was 90.03-99.99%. In addition, the metabolic concentration of chiral amino acids was monitored after drinking red wine and white wine, and the fitting curve of metabolic concentration was drawn | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Chiral amino enantiomer | |
| 650 | 4 | |a Chiral separation | |
| 650 | 4 | |a Diphenyl sulfide | |
| 650 | 4 | |a UHPLC-MS/MS | |
| 650 | 4 | |a Wine | |
| 650 | 7 | |a Amino Acids |2 NLM | |
| 650 | 7 | |a diphenyl sulfide |2 NLM | |
| 650 | 7 | |a B5P3Y93MNR |2 NLM | |
| 650 | 7 | |a Indicators and Reagents |2 NLM | |
| 650 | 7 | |a Amines |2 NLM | |
| 700 | 1 | |a Cheng, Shengyu |e verfasserin |4 aut | |
| 700 | 1 | |a Zhu, Yan |e verfasserin |4 aut | |
| 700 | 1 | |a Jin, Yueying |e verfasserin |4 aut | |
| 700 | 1 | |a Qi, Chao |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Lingli |e verfasserin |4 aut | |
| 700 | 1 | |a Zhang, Minghui |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Xin |e verfasserin |4 aut | |
| 700 | 1 | |a Han, Yu |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Xi-Ling |e verfasserin |4 aut | |
| 700 | 1 | |a Min, Jun Zhe |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Journal of chromatography. A |d 1993 |g 1688(2023) vom: 11. Jan., Seite 463698 |w (DE-627)NLM074731416 |x 1873-3778 |7 nnns |
| 773 | 1 | 8 | |g volume:1688 |g year:2023 |g day:11 |g month:01 |g pages:463698 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1016/j.chroma.2022.463698 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 1688 |j 2023 |b 11 |c 01 |h 463698 | ||