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 language | English |
|---|---|
| Pages (from-to) | 103-108 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 62 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 1997 |
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- Organic Chemistry
Cite this
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 journal › Article
}
TY - JOUR
T1 - Pholipeptin, a novel cyclic lipoundecapeptide from Pseudomonas fluorescens
AU - Ui, Hideaki
AU - Miyake, Toshiaki
AU - Iinuma, Hironobu
AU - Imoto, Masaya
AU - Naganawa, Hiroshi
AU - Hattori, Seiko
AU - Hamada, Masa
AU - Takeuchi, Tomio
AU - Umezawa, Sumio
AU - Umezawa, Kazuo
PY - 1997
Y1 - 1997
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=8044225291&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=8044225291&partnerID=8YFLogxK
U2 - 10.1021/jo9603993
DO - 10.1021/jo9603993
M3 - Article
AN - SCOPUS:8044225291
VL - 62
SP - 103
EP - 108
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 1
ER -