Chemical assay-guided natural product isolation via solid-supported chemodosimetric fluorescent probe

Jeon, Hongjun; Lim, Chaemin; Lee, Ji Min; Kim, Sanghee

doi:10.1039/c5sc00360a

Cited by 30 publications

(24 citation statements)

References 41 publications

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“…An additional challenge during these solid‐phase protocols lies in how to release captured molecules from resins. Kim and co‐workers developed the hetero‐bifunctional SCF15 linker containing the (2‐phenyl‐2‐trimethylsilyl)ethyl moiety, which could be cleaved by fluoride ions under mild conditions . SCF15‐resin was fabricated through standard solid‐phase procedures, starting from TentaGel™ MB amine resin and SCF15 linker.…”

Section: Fluorogenic Bifunctional Linkersmentioning

confidence: 99%

“…Terminal alkyne (TA)‐containing target molecules extracted from stem heartwood were enriched by SCF15‐resin through fluorogenic CuAAC reactions. The resulting fluorescent TA‐SCF15 was then cleaved from the resin upon treatment with tetrabutylammonium fluoride (TBAF) and subsequently analyzed by LC/MS (Figure ) . Wong et al.…”

Section: Fluorogenic Bifunctional Linkersmentioning

confidence: 99%

“…TA‐containing natural products were then captured by SCF15 resin through the CuAAC reaction, exhibiting fluorescence emission turn‐on. TA‐SCF15 was then released from resins upon triggering with F − ions …”

Section: Fluorogenic Bifunctional Linkersmentioning

confidence: 99%

“…Kim and co-workers developedt he hetero-bifunctional SCF15 linker containing the (2-phenyl-2-trimethylsilyl)ethyl moiety,w hich could be cleaved by fluoridei ons under mild conditions. [70] SCF15-resin wasf abricated through standard solid-phase procedures, startingf rom Te ntaGel MB amine resin and SCF15 linker.T erminal alkyne (TA)-containingt arget molecules extracted from stem heartwood were enriched by SCF15-resin through fluorogenic CuAAC reactions. The resulting fluorescent TA-SCF15w as then cleaved from the resin upon treatment with tetrabutylammonium fluoride (TBAF)a nd subsequently analyzed by LC/MS (Figure 15).…”

Section: Hetero-bifunctional Scf Linkersmentioning

confidence: 99%

“…The resulting fluorescent TA-SCF15w as then cleaved from the resin upon treatment with tetrabutylammonium fluoride (TBAF)a nd subsequently analyzed by LC/MS (Figure 15). [70] Wong et al reported the SCF16 linker for fluorogenically guided isolationa nd analysiso fa lkynyl-functionalized glycoproteins generated through metabolic oligosaccharidel abeling ( Figure 15). [71]…”

Section: Hetero-bifunctional Scf Linkersmentioning

confidence: 99%

See 4 more Smart Citations

Emerging Applications of Fluorogenic and Non‐fluorogenic Bifunctional Linkers

Liu

2018

Chemistry A European J

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Homo- and hetero-bifunctional linkers play vital roles in constructing a variety of functional systems, ranging from protein bioconjugates with drugs and functional agents, to surface modification of nanoparticles and living cells, and to the cyclization/dimerization of synthetic polymers and biomolecules. Conventional approaches for assaying conjugation extents typically rely on ex situ techniques, such as mass spectrometry, gel electrophoresis, and size-exclusion chromatography. If the conjugation process involving bifunctional linkers was rendered fluorogenic, then in situ monitoring, quantification, and optical tracking/visualization of relevant processes would be achieved. In this review, conventional non-fluorogenic linkers are first discussed. Then the focus is on the evolution and emerging applications of fluorogenic bifunctional linkers, which are categorized into hetero-bifunctional single-caging fluorogenic linkers, homo-bifunctional double-caging fluorogenic linkers, and hetero-bifunctional double-caging fluorogenic linkers. In addition, stimuli-cleavable bifunctional linkers designed for both conjugation and subsequent site-specific triggered release are also summarized.

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Section: Fluorogenic Bifunctional Linkersmentioning

confidence: 99%

Section: Fluorogenic Bifunctional Linkersmentioning

confidence: 99%

Section: Fluorogenic Bifunctional Linkersmentioning

confidence: 99%

Section: Hetero-bifunctional Scf Linkersmentioning

confidence: 99%

Section: Hetero-bifunctional Scf Linkersmentioning

confidence: 99%

See 3 more Smart Citations

Emerging Applications of Fluorogenic and Non‐fluorogenic Bifunctional Linkers

Liu

2018

Chemistry A European J

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Chemoselective Tagging to Promote Natural Product Discovery

Tollefson

Carlson

2019

Mass Spectrometry‐Based Chemical Proteomics

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Chemical Toolbox to Decode the Microbiota Lexicon

Qiao

Hayashi

Teo

2020

Chemistry An Asian Journal

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The human microbiota deploys a diverse range of molecules and metabolites to engage in chemical communications with the host, mediating fundamental aspects of host health. Studies of the structures and activities of bioactive molecules produced by the microbiota are imperative to address their implications in microbiota associated diseases in human. By drawing experiences from different research fields, chemists and chemical biologists, who are experts in dealing with chemical molecules, are uniquely positioned to contribute to the emerging knowledge of human microbiota. In this minireview, we discuss the current chemical tools and methods that are pertinent to the discovery of microbiota molecules and metabolites, characterizations of their protein targets, as well as evaluations of their biodistributions in hosts. These are key aspects in understanding the chemical underpinnings of the microbiota-host interactions that would enable future development of diagnostics and therapeutics targeting the human microbiota.

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Chemical assay-guided natural product isolation via solid-supported chemodosimetric fluorescent probe

Abstract: The fusion of click chemistry, fluorogenic chemodosimetry and a solid support offers advantages in identifying compounds in complex natural product mixtures.

Cited by 30 publications

References 41 publications

Emerging Applications of Fluorogenic and Non‐fluorogenic Bifunctional Linkers

Emerging Applications of Fluorogenic and Non‐fluorogenic Bifunctional Linkers

Chemoselective Tagging to Promote Natural Product Discovery

Chemical Toolbox to Decode the Microbiota Lexicon

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