Pholipeptin, a Novel Cyclic Lipoundecapeptide from Pseudomonas fluorescensClick to copy article linkArticle link copied!
- Hideaki Ui
- Toshiaki Miyake
- Hironobu Iinuma
- Masaya Imoto
- Hiroshi Naganawa
- Seiko Hattori
- Masa Hamada
- Tomio Takeuchi
- Sumio Umezawa
- Kazuo Umezawa
Abstract

An inhibitor of phosphatidylinositol-specific phospholipase C (PI-PLC), pholipeptin (1), was purified from the culture broth of Pseudomonas sp. by solvent extraction and column chromatography. Acid hydrolysis of 1 gave Leu, Ile, Ser, Thr, and Asp moieties. Although 1 was a peptide compound, fragmentation by mild hydrolysis was not accomplished under any conditions. So, we performed the structure elucidation using various 2D NMR techniques. In the NMR studies, the addition of a small amount of trifluoroacetic acid gave relatively sharp and resolved signals, such that the structure of this novel cyclic lipodepsipeptide consisting of 11 amino acids and a 3-hydroxydecanoic acid moiety could be determined. Chirality of the constituent amino acids was analyzed by chiral HPLC, but two Asp residues could not be distinguished because they were contained as a racemic mixture. Finally, their chiralities were determined by NMR analysis of 13C-labeled 1 into which [l-13C]Asp had been biosynthetically incorporated.
†
Keio University.
‡
Institute of Bioorganic Chemistry.
§
Institute of Microbial Chemistry.
*
To whom correspondence should be addressed. Tel.: +81-45-563-1141 ext. 3481. Fax: +81-45-562-7625.
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Abstract published in Advance ACS Abstracts, December 15, 1996.
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