Pholipeptin, a novel cyclic lipoundecapeptide from Pseudomonas fluorescens

Hideaki Ui, Toshiaki Miyake, Hironobu Iinuma, Masaya Imoto, Hiroshi Naganawa, Seiko Hattori, Masa Hamada, Tomio Takeuchi, Sumio Umezawa, Kazuo Umezawa

Research output: Contribution to journalArticle

23 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)103-108
Number of pages6
JournalJournal of Organic Chemistry
Volume62
Issue number1
DOIs
Publication statusPublished - 1997

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Chirality
Nuclear magnetic resonance
Hydrolysis
Phosphoinositide Phospholipase C
Amino Acids
Trifluoroacetic Acid
Column chromatography
Solvent extraction
Peptides
Acids
myrmicacin

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Ui, H., Miyake, T., Iinuma, H., Imoto, M., Naganawa, H., Hattori, S., ... Umezawa, K. (1997). Pholipeptin, a novel cyclic lipoundecapeptide from Pseudomonas fluorescens. Journal of Organic Chemistry, 62(1), 103-108. https://doi.org/10.1021/jo9603993

Pholipeptin, a novel cyclic lipoundecapeptide from Pseudomonas fluorescens. / Ui, Hideaki; Miyake, Toshiaki; Iinuma, Hironobu; Imoto, Masaya; Naganawa, Hiroshi; Hattori, Seiko; Hamada, Masa; Takeuchi, Tomio; Umezawa, Sumio; Umezawa, Kazuo.

In: Journal of Organic Chemistry, Vol. 62, No. 1, 1997, p. 103-108.

Research output: Contribution to journalArticle

Ui, H, Miyake, T, Iinuma, H, Imoto, M, Naganawa, H, Hattori, S, Hamada, M, Takeuchi, T, Umezawa, S & Umezawa, K 1997, 'Pholipeptin, a novel cyclic lipoundecapeptide from Pseudomonas fluorescens', Journal of Organic Chemistry, vol. 62, no. 1, pp. 103-108. https://doi.org/10.1021/jo9603993
Ui, Hideaki ; Miyake, Toshiaki ; Iinuma, Hironobu ; Imoto, Masaya ; Naganawa, Hiroshi ; Hattori, Seiko ; Hamada, Masa ; Takeuchi, Tomio ; Umezawa, Sumio ; Umezawa, Kazuo. / Pholipeptin, a novel cyclic lipoundecapeptide from Pseudomonas fluorescens. In: Journal of Organic Chemistry. 1997 ; Vol. 62, No. 1. pp. 103-108.
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