Chemo- and site-selective derivatizations of natural products enabling biological studies
Open accessAbstract
The direct chemo- and site-selective modification of native bioactive natural products (NP) for structure–activity relationship (SAR) studies and cellular probe synthesis has recently begun to be addressed (FG = functional group). This review highlights selected recent examples of these functionalization strategies, including those that simultaneously introduce a linker and reactive group (gray structure) for subsequent conjugation to reporter tags.
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Molecules containing alcoholic and phenolic functional groups are often very polar and are not efficiently retained on common reversed-phase columns, and they are mainly analyzed under negative polarity on the mass spectrometer.
“However, molecules containing alcoholic and phenolic functional groups are often very polar and are not efficiently retained on common reversed-phase columns, and they are mainly analyzed under negative polarity on the mass spectrometer.107”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [107]
Section 2.1 (page unavailable) says hydroxyl groups in natural products are likely present to improve water solubility, which lends limited support to the claim about polarity. The paper does not support the attributed claims about poor retention on reversed-phase columns or predominant negative-polarity mass-spectrometric analysis. (LLM, conf=0.78)
Experimental — accuracy not yet measuredThese 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 [107]
Section 2.1 discusses acylating reagents and says a less reactive reagent improved site selectivity, but does not say these strategies generally require strong electrophiles. Section 2.2 gives an O–H insertion reactivity order, not a general comparison of phenol and alcohol nucleophilicity. Searches for the claimed electrophile requirement and nucleophilicity comparison found no passage stating them. (LLM, conf=0.72)
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References 81 · Cited by 154
Research works printed but not linked: 2
- [52]Barton DHR McCombie SW J. Chem. Soc., Perkin Trans. 1 1975 1574 1585
- [56]Sánchez-Roselló M Puchlopek ALA Morgan AJ Miller SJ J. Org. Chem 2008 73 1774 1782 18229939 PMC4189089
- Authors
- Robles, O., & Romo, D.
- Affiliations
- Texas A&M University (US)
- Corresponding author
- Romo, Daniel
- Venue
- Nat. Prod. Rep.
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2014
- Volume
- 31
- Issue
- 3
- Pages
- 318-334
- ISSN
- 0265-0568 (ISSN-L)
- 1460-4752
- PMC
- PMC4041598
- OpenAlex
- W2001818849
- Cited by
- 154
- References
- 81
- Citations by year
- 2026: 5 · 2025: 14 · 2024: 14 · 2023: 13 · 2022: 14 · 2021: 8 · 2020: 15 · 2019: 9 · 2018: 6 · 2017: 11 · 2016: 23 · 2015: 14 · 2014: 8
- FWCI
- 1.01
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Natural Product Reports (publishedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Institutes of Health
- National Institute of General Medical Sciences (GM 086307, R01GM086307)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Click Chemistry and Applications
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Natural product bioactivities and synthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
- Keywords
- site-selective modification, natural products, mechanism of action, affinity chromatography, proteomic profiling, structure-activity relationship, lead compound development
- MeSH terms
- Biological Products, Structure-Activity Relationship, Molecular Structure, Drug Discovery
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