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Pholipeptin, a Novel Cyclic Lipoundecapeptide from Pseudomonas fluorescens
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    Pholipeptin, a Novel Cyclic Lipoundecapeptide from Pseudomonas fluorescens
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    Department 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
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1997, 62, 1, 103–108
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    https://doi.org/10.1021/jo9603993
    Published January 10, 1997
    Copyright © 1997 American Chemical Society

    Abstract

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    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.

    Copyright © 1997 American Chemical Society

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     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.

     Abstract published in Advance ACS Abstracts, December 15, 1996.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 1997, 62, 1, 103–108
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo9603993
    Published January 10, 1997
    Copyright © 1997 American Chemical Society

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