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Pholipeptin, a Novel Cyclic Lipoundecapeptide fromPseudomonas fluorescens
Hideaki Ui1, Toshiaki Miyake, Hironobu Iinuma
1Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223, Japan, Institute of Bioorganic Chemistry, 3-34-17 Ida, Nakahara-ku, Kawasaki 211, Japan, and Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan.
The Journal of Organic Chemistry
|January 10, 1997
Summary
Pholipeptin, a novel cyclic lipodepsipeptide, was identified as a phosphatidylinositol-specific phospholipase C inhibitor. Its complex structure was elucidated using advanced NMR techniques and chiral analysis.
Area of Science:
- Microbiology
- Natural Product Chemistry
- Biochemistry
Background:
- Pholipeptin (1) is an inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC).
- The compound was isolated from the culture broth of Pseudomonas sp.
Purpose of the Study:
- To elucidate the novel structure of pholipeptin (1).
- To determine the chirality of the constituent amino acids.
Main Methods:
- Purification using solvent extraction and column chromatography.
- Structure elucidation via 2D NMR techniques, aided by trifluoroacetic acid for signal resolution.
- Chiral analysis using chiral HPLC and (13)C-labeled NMR spectroscopy.
Main Results:
- Pholipeptin (1) was identified as a cyclic lipodepsipeptide.
- The structure comprises 11 amino acids and a 3-hydroxydecanoic acid moiety.
- Chiral analysis revealed a racemic mixture for two Asp residues, with their specific chiralities determined through biosynthetic incorporation of labeled amino acids.
Conclusions:
- The complete structure of pholipeptin (1), a novel cyclic lipodepsipeptide inhibitor of PI-PLC, was determined.
- Advanced NMR and chiral analysis methods were crucial for structural elucidation.
- The study highlights the complexity of natural product characterization.