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Lipoamino acid


DATA No : ALA0004 INFORMANT : Youko Kawai

NAME : a-N-[3-(isopentadecanoyloxy)isoheptadecanoyl]-glycyl-serine

COMMON NAME: Flavolipin, Ser-Gly-lipid, Ser-Gly-containing lipid
SYMBOL:
FORMULA: C37H69O7N2 MOL.WT (average) : 653.953


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Macrophage activation was observed (Ref. 0006). PGE2- and IL-1-inducing activities were strong. The structure is similar to the OL
[Table 0011].
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:
[Spectrum 0009]Ester-linkage 1730 and secondary amide linkage, (Ref. 0004)

NMR SPECTRA:
[Spectrum 0012]The spectra of Flavolipin and the synthetic Flavolipin was identical. (Ref. 0010)

MASS SPECTRA:
[Spectrum 0010] Negative FAB mass. Flavolipin and
[Spectrum 0011]Synthetic Flavolipin. These spectra was identical. Positive FAB mass ( Molecular ion 654) (Ref. 0010)

OTHER SPECTRA:
CHROMATOGRAM DATA

[Chromatogram 0003] TLC of the free lipid of Flavobacterium
SOURCE
Ser-Gly-lipid is vary rare. It is found only in Flavobacterium. (Ref. 0004)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0004]
AUTHOR:Kawai, Y., Yano, I., and Kaneda, K.
TITLE:Various kinds of lipoamino acids including a novel serine-containing lipid in an opportunistic pathogen Flavobacterium. Their structures and biological activities on erythrocytes PubMed ID:3123236
JOURNAL:Eur J Biochem.
VOL:171 PAGE : 73-80 (1988)
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[0006]
AUTHOR:Kawai, Y., and Akagawa, K.
TITLE:Macrophage activation by an ornithine-containing lipid or a serine-containing lipid PubMed ID:2499544
JOURNAL:Infect Immun.
VOL:57 PAGE : 2086-2091 (1989)
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[0010]
AUTHOR:Shiozaki, M., Deguchi, N., Mochizuki, T., Wakabayashi, T., Ishikawa, T., Haruyama, H., Kawai, Y., and Nishijima, M.
TITLE:Revised structure and synthesis of Flavolipin.
JOURNAL:Tetra hedron
VOL:54 PAGE : 11861 -11876 (1998)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.