Chemical labeling strategies for small molecule natural product detection and isolation
Abstract
Chemical labeling enhances the analysis of complex mixtures via HPLC-MS in both targeted and untargeted metabolomics workflows.
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Several NPs, such as spiramycin, kitasamycin, and rotenone, contain carbonyl groups, and in some NPs, the carbonyl groups are known to participate in the interaction with a biological target.
“Several NPs, such as spiramycin, kitasamycin, and rotenone, contain carbonyl groups, and in some NPs, the carbonyl groups are known to participate in the interaction with a biological target.21,112”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [21]
These strategies generally employ strong electrophiles as DAs since the phenolic group is a weak nucleophile and the alcoholic group is even weaker.
“These strategies generally employ strong electrophiles as DAs since the phenolic group is a weak nucleophile and the alcoholic group is even weaker.21,107”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [21]
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 [21]
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References 221 · Cited by 31
- Authors
- Hughes, C. C.
- Affiliations
- University of Tübingen (DE)
- Corresponding author
- Hughes, Chambers C.
- ORCID
- Hughes, Chambers C.
- Venue
- Natural Product Reports
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2021
- Volume
- 38
- Issue
- 9
- Pages
- 1684-1705
- ISSN
- 0265-0568 (ISSN-L)
- 1460-4752
- OpenAlex
- W3130785777
- Cited by
- 31
- References
- 221
- Citations by year
- 2026: 2 · 2025: 8 · 2024: 4 · 2023: 6 · 2022: 7 · 2021: 4
- FWCI
- 0.55
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Natural Product Reports (publishedVersion)
- PubMed (publishedVersion)
- Funders
- American Cancer Society (ACS-IRG Grant 15-172-45)
- University of California, San Diego (RN143S-HUGHES, RP42S-HUGHES)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Metabolomics and Mass Spectrometry Studies
- Physical Sciences › Chemistry › Spectroscopy › Mass Spectrometry Techniques and Applications
- Physical Sciences › Chemistry › Analytical Chemistry › Chromatography in Natural Products
- Keywords
- chemical labeling, derivatization, derivatization reagents, chemoselectivity, natural product isolation, targeted metabolomics, amine derivatization, carboxylic acid derivatization, thiol derivatization, terminal alkynes, isocyanides
- MeSH terms
- Biological Products, Chromatography, High Pressure Liquid, Mass Spectrometry, Small Molecule Libraries
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