Synthesis of benzofurazan derivatization reagents for short chain carboxylic acids in liquid chromatography/electrospray ionization‐tandem mass spectrometry (LC/ESI‐MS/MS)
Abstract
Benzofurazan derivatization reagents, 4‐[2‐(N,N‐dimethylamino)ethylaminosulfonyl]‐7‐(2‐aminopentylamino)‐2,1,3‐benzoxadiazole (DAABD‐AP) and 4‐[2‐(N,N‐dimethylamino) ethylaminosulfonyl]‐7‐(2‐aminobutylamino)‐2,1,3‐benzoxadiazole (DAABD‐AB), for short‐chain carboxylic acids in liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI‐MS/MS) were synthesized. These reagents reacted with short chain carboxylic acids in the presence of the condensation reagents at 60°C for 60 min. The generated derivatives were separated on the reversed‐phase column and detected by ESI‐MS/MS with the detection limits of 0.1–0.12 pmol on column. Upon collision‐induced dissociation, a single and intense product ion at m/z 151 was observed. These results indicated that DAABD‐AP and DAABD‐AB are suitable as the derivatization reagents in LC/ESI‐MS/MS analysis. Copyright © 2008 John Wiley & Sons, Ltd.
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Amines are usually the first choice for derivatizing carboxyls, and these DAs typically contain an aromatic ring or quaternary nitrogen that improves UV absorption and ionization in positive mode.
“Amines are usually the first choice for derivatizing carboxyls, and these DAs typically contain an aromatic ring or quaternary nitrogen that improves UV absorption and ionization in positive mode (in contrast to the carboxyl group that is ionized under negative polarity).21,113”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [113]
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References 18 · Cited by 17
- Authors
- Santa, T., Al‐Dirbashi, O. Y., Yoshikado, T., Fukushima, T., & Imai, K.
- Affiliations
- The University of Tokyo (JP)
- King Faisal Specialist Hospital & Research Centre (SA)
- Toho University (JP)
- Musashino University (JP)
- Corresponding author
- Santa, Tomofumi
- Venue
- Biomedical Chromatography
- Publisher
- Wiley
- Published
- 2008-11-17
- Volume
- 23
- Issue
- 4
- Pages
- 443-446
- ISSN
- 0269-3879 (ISSN-L)
- 1099-0801
- OpenAlex
- W2075739230
- Cited by
- 17
- References
- 18
- Citations by year
- 2024: 1 · 2023: 1 · 2021: 2 · 2020: 1 · 2018: 2 · 2016: 1 · 2014: 2 · 2012: 1
- FWCI
- 0.72
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Biomedical Chromatography (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Japan Society for the Promotion of Science (21590039)
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Mass Spectrometry Techniques and Applications
- Physical Sciences › Chemistry › Spectroscopy › Analytical Chemistry and Chromatography
- Physical Sciences › Chemistry › Analytical Chemistry › Analytical chemistry methods development
- Keywords
- short-chain carboxylic acids, collision-induced dissociation
- MeSH terms
- Benzoxazoles, Carboxylic Acids, Chromatography, High Pressure Liquid, Oxadiazoles, Sulfonamides, Spectrometry, Mass, Electrospray Ionization, Tandem Mass Spectrometry
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