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Isoprenoid


DATA No : IIP0072 INFORMANT : Yoshichika Yoshioka

NAME : [6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62Z,66Z,70Z,74Z,78E,82E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79,83,87-Docosamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78,82,86-octaoctacontahenicosaen-1-yl monophosphate

COMMON NAME: Dolichyl-22 monophosphate, a-Dihydrodocosaprenyl monophosphate
SYMBOL: Dol-22-P
FORMULA: C110H181O4P MOL.WT (average) : 1598.586


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BIOLOGICAL ACTIVITY
The biological role of dolichol (review)(Ref. 0043). Dolichyl phosphate is a potent inducer of apoptosis in rat glioma cells. Apoptotic changes were also observed in HL-60 cells, SIRC cells and HeLa cells(Ref. 0098). Treatment of U937 cells with dolichyl phosphate led to an increase in the activity of the ICE family protease CPP32, accompanied with cleavage of pre-CPP32 to generate p17. The modulation od cAMP synthesis due to the stimulation of adenylate cyclase by dolichyl phosphate plays a critical role in CPP32 activation and apoptosis(Ref. 0100).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA
HPLC (with chromatograph)(Ref. 0048/0051).
SOURCE
Human liver and testis(Ref. 0048). Rat and human tissues (spleen, liver, kidney, myocardium, lung, pancreas, adrenal)(Ref. 0051).
CHEMICAL SYNTHESIS

METABOLISM
Rat liver hyperplastic nodules(Ref. 0048). Human liver cirrosis and hepatocarcinoma(Ref. 0048). Age-related chnges of dolichyl phosphate content in rat and human tissues (spleen, liver, kidney, heart, lung, pancreas, adrenal)(Ref. 0051). Contents of various organs of mice used as a model for Niemann-Pick's type C disease (liver, spleen, kidney, brain, testis, lung, adipose tissue, heart, intestine, skeletal muscle). Contents in subfractions isolated from the liver of mice used as a model for NPC (mitocondria, lysosomes, microsomes)(Ref. 0071).
GENETIC INFORMATION

NOTE

REFERENCES
[0043]
AUTHOR:Chojnacki, T., and Dallner, G.
TITLE:The biological role of dolichol PubMed ID:3291859
JOURNAL:Biochem J.
VOL:251 PAGE : 1-9 (1988)
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[0048]
AUTHOR:Eggens, I., Chojnacki, T., Kenne, L., and Dallner, G.
TITLE:Separation, quantitation and distribution of dolichol and dolichyl phosphate in rat and human tissues PubMed ID:6849949
JOURNAL:Biochim Biophys Acta.
VOL:751 PAGE : 355-368 (1983)
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[0051]
AUTHOR:Kalen, A., Appelkvist, E. L., and Dallner, G.
TITLE:Age-related changes in the lipid compositions of rat and human tissues PubMed ID:2779364
JOURNAL:Lipids.
VOL:24 PAGE : 579-584 (1989)
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[0071]
AUTHOR:Schedin, S., Pentchev, P. G., Brunk, U., and Dallner, G.
TITLE:Changes in the levels of dolichol and dolichyl phosphate in a murine model of Niemann-Pick's type C disease PubMed ID:7616223
JOURNAL:J Neurochem.
VOL:65 PAGE : 670-676 (1995)
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[0098]
AUTHOR:Yasugi, E., Yokoyama, Y., Seyama, Y., Kano, K., Hayashi, Y., and Oshima, M.
TITLE:Dolichyl phosphate, a potent inducer of apoptosis in rat glioma C6 cells PubMed ID:7488203
JOURNAL:Biochem Biophys Res Commun.
VOL:216 PAGE : 848-853 (1995)
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[0100]
AUTHOR:Yokoyama, Y., Okubo, T., Ozawa, S., Nagai, F., Ushiyama, K., Kano, I., Shioda, M., Kubo, H., Takemura, M., Namiki, H., et al.
TITLE:CPP32 activation during dolichyl phosphate-induced apoptosis in U937 leukemia cells PubMed ID:9257710
JOURNAL:FEBS Lett.
VOL:412 PAGE : 153-156 (1997)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.