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
N1 - Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.
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.
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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 -