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Highly Sensitive Labeling Reagents for Scarce Natural Products
Takefumi Kuranaga1, Mayuri Minote1, Ryota Morimoto1
1Department of System Chemotherapy and Molecular Sciences, Division of Bioinformatics and Chemical Genomics, Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
ACS Chemical Biology
|September 1, 2020
Summary
Researchers developed highly sensitive labeling reagents for analyzing scarce natural products. These tools enhance detection of amino acids and other biomolecules, aiding drug discovery from rare compounds.
Area of Science:
- Natural Product Chemistry
- Analytical Chemistry
- Organic Synthesis
Background:
- Scarce natural products are valuable drug leads due to unique biological activities.
- Identifying and determining structures of rare compounds is challenging due to limited sample amounts.
- Yaku'amide B (10) is an extremely rare natural product that inspired the development of new analytical tools.
Purpose of the Study:
- To design and synthesize highly sensitive labeling reagents for scarce natural product chemistry.
- To enhance detection sensitivity in liquid chromatography-mass spectrometry (LC-MS) analysis.
- To provide powerful tools for the identification and structural determination of trace natural products.
Main Methods:
- Design and synthesis of novel labeling reagents.
- Fusion of reagents with a key structural motif from yaku'amide B.
- Application of reagents in LC-MS analysis for enhanced detection.
- Testing applicability for saccharide labeling and electrophilic natural product isolation.
Main Results:
- Drastically enhanced detection sensitivities for amino acid labeling reagents in LC-MS.
- Successful detection of infinitesimal amounts of amino acids and peptide hydrolysates.
- Demonstrated applicability of the sensitivity-enhancement design concept to saccharide labeling.
- Showcased utility in reactivity-guided isolation of electrophilic natural products.
Conclusions:
- The developed labeling reagents are powerful tools for analyzing scarce natural products.
- The sensitivity-enhancement design strategy significantly improves detection limits.
- These reagents offer broad applications in natural product chemistry, aiding drug discovery efforts.
