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Lipoamino acid


DATA No : ALA0001 INFORMANT : Youko Kawai

NAME : a-N-(D)-[3-(hexadecanoyloxy)hexadecanoyl]-L-ornithine (Ref. 0001/0003/0005/0011)

COMMON NAME: typical bacterial ornithine-containing lipid
SYMBOL: OL , Orn-lipid
FORMULA: C37H72O5N2 MOL.WT (average) : 624.978


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BIOLOGICAL ACTIVITY
Hemagglutinating-activity , minimum hemagglutinating concentration on human erythrocyte is 1 mg/ml.
[Table 0001] (Ref. 0001/0003) , Hemolitic activity of O-deacylated OL,
[Table 0003] (Ref. 0001), Inhibition of hemagglutination
[Table 0002] (Ref. 0001), Macrophage activation , PGE2 and IL-1- inducing activities, nontoxic (nonlethality, and non TNF-inducing activity) (Ref. 0009/0011), the structure of the OL is similar to the structure of lipid A of bacterial LPS
[Table 0004].
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:155-156 degC

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D25 +1.8

DENSITY:

SOLUBILITY:Soluble in chloroform/methanol (2:1)
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:
[Spectrum 0001] Ester linkage (1730 cm-1), Secondary amide linkage (1640 and 1540 cm-1)(Ref. 0001) (Ref. 0005)

NMR SPECTRA:

MASS SPECTRA:
[Spectrum 0002] OL of B. pertussis, Trimethylsilyl OL, Molecular ion 606 (M-90, loss of trimethylsilyl) ,
[Spectrum 0003] OL of B. pertussis, Trimethylsilyl O-deacylated OL, Molecular ion 425 ( M-105, loss of trimethylsilyl and methyl),
[Spectrum 0004] OL of P. fluorescens, two Molecular ions , 623 (typical OL) and 651 (Orn-3-OH 18:1-16:0 plus Orn-3-OH 16:0-18:1) (Ref. 0001/0003/0005)

OTHER SPECTRA:
CHROMATOGRAM DATA

[Chromatogram 0001] TLC pattern of neutral solvent extractable lipid of B. pertussis . the OL is located just below of phosphatidylethanolamine (Ref. 0002).
[Chromatogram 0002] TLC pattern of neutral solvent extractable lipid of Pseudomonas (Ref. 0005)
SOURCE
distributed in various bacteria such as Bordetella pertussis, B. parapertussis, B. bronchisepticum , Pseudomonas fluorescens, P. aeruginosa, P. stuteri, P. cepacia, Achromobacter xylosoxidans, Serratia marcescens and Rhodopseudomonas spheroides. (Ref. 0001/0005/0011/0012)
CHEMICAL SYNTHESIS
Synthesis of the ornithine containing lipid are described in the litarature (Ref. 0011)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0001]
AUTHOR:Kawai, Y., and Yano, I.
TITLE:Ornithine-containing lipid of Bordetella pertussis, a new type of hemagglutinin PubMed ID:6315433
JOURNAL:Eur J Biochem.
VOL:136 PAGE : 531-538 (1983)
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[0002]
AUTHOR:Kawai, Y.
TITLE:Characteristic cellular fatty acid composition and an ornithine-containing lipid as a new type of hemagglutinin in Bordetella pertussis PubMed ID:2872110
JOURNAL:Dev Biol Stand.
VOL:61 PAGE : 249-254 (1985)
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[0003]
AUTHOR:Kawai, Y., Moribayashi, A., and Yano, I.
TITLE:Ornithine-containing lipid of Bordetella pertussis that carries hemagglutinating activity PubMed ID:6290456
JOURNAL:J Bacteriol.
VOL:152 PAGE : 907-910 (1982)
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[0005]
AUTHOR:Kawai, Y., Yano, I., Kaneda, K., and Yabuuchi, E.
TITLE:Ornithine-containing lipids of some Pseudomonas species PubMed ID:3409887
JOURNAL:Eur J Biochem.
VOL:175 PAGE : 633-641 (1988)
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[0009]
AUTHOR:Kawai, Y., Takasuka, N., Akagawa, K., and Naito, S.
TITLE:Hypothermic response of mice to ornithine-containing lipids and to endotoxin PubMed ID:8675313
JOURNAL:Infect Immun.
VOL:64 PAGE : 2101-2105 (1996)
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[0011]
AUTHOR:Kawai, Y., Nakagawa, Y., Matuyama, T., Akagawa, K., Itagawa, K., Fukase, K., Kusumoto, S., Nishijima, M., and Yano, I.
TITLE:A typical bacterial ornithine-containing lipid Nalpha-(D)-[3-(hexadecanoyloxy)hexadecanoyl]-ornithine is a strong stimulant for macrophages and a useful adjuvant PubMed ID:10030549
JOURNAL:FEMS Immunol Med Microbiol.
VOL:23 PAGE : 67-73 (1999)
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[0012]
AUTHOR:Miyazaki, Y., Oka, S., Hara-Hotta, H., and Yano, I.
TITLE:Stimulation and inhibition of polymorphonuclear leukocytes phagocytosis by lipoamino acids isolated from Serratia marcescens PubMed ID:8388762
JOURNAL:FEMS Immunol Med Microbiol.
VOL:6 PAGE : 265-271 (1993)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.