Back to HOME

Isoprenoid


DATA No : IIP0006 INFORMANT : Yoshichika Yoshioka

NAME : [2E,6E,10E]-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-yl diphosphate

COMMON NAME: Geranylgeranyl diphosphate, Geranylgeranyl pyrophosphate
SYMBOL: GGOPP, GGPP
FORMULA: C20H36O7P2 MOL.WT (average) : 450.443


Download ChemDraw structure data
BIOLOGICAL ACTIVITY
Rat liver microsomes catalyzed the formation of Z,E,E-geranylgeranyl diphosphate from farnesyl diphosphate and isopentenyl diphosphate in the presence of Triton X-100(Ref. 0026). HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture. Geranylgeranylpyrophosphate and mevalonate completely reversed the effect of the inhibitors, while farnesylpyrophosphate partially reversed it and dolichol had no effect(Ref. 0064).
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

SOURCE

CHEMICAL SYNTHESIS
The compound can be synthesized from geranylgeraniol .(Ref. 0014)
METABOLISM
The product formed by the action of geranylgeranyl diphosphate synthase. The rate of de novo synthesis of geranylgeranyl diphosphate from mevalonic acid is comparable to that of farnesyl diphosphate(Ref. 0078). Geranylgeranyl diphosphate synthase catalyzing the single condensation between isopentenyl diphosphate and farnesyl diphosphate. The enzyme required Mg2+ and Mn2+ for maximum activity. Octylglucoside showed a stimulatory effect on the enzyme activity. Farnesyl diphosphate is the common intermediate at the branch point for the synthesis of geranylgeranylated proteins as well as cholesterol, ubiquinone, dolichol, and farnesylated proteins(Ref. 0070). Purification and properties of geranylgeranyl-diphosphate synthase from bovine brain(Ref. 0080). The uptake of F-PP and GG-PP was studied using primary cultures of chromaffin cells. Dolichylmonophosphate and isopentenylpyrophosphate promoted the uptake(Ref. 0079). The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039).
GENETIC INFORMATION
The nucleotide sequences of yeast Saccharomyces cerevisiae and human geranylgeranyl diphosphate synthase have been reported in (Ref. 0011)and (Ref. 0016). African swine fever virus trans-polyprenyltransferase also catalyzes mainly geranylgeranyl diphosphate from farnesyl diphosphate and isopentenyl diphosphate. (Ref. 0013)
NOTE

REFERENCES
[0011]
AUTHOR:Jiang, Y., Proteau, P., Poulter, D., and Ferro-Novick, S.
TITLE:BTS1 encodes a geranylgeranyl diphosphate synthase in Saccharomyces cerevisiae PubMed ID:7665600
JOURNAL:J Biol Chem.
VOL:270 PAGE : 21793-21799 (1995)
[TOP]

[0013]
AUTHOR:Alejo, A., Yanez, R. J., Rodriguez, J. M., Vinuela, E., and Salas, M. L.
TITLE:African swine fever virus trans-prenyltransferase PubMed ID:9083080
JOURNAL:J Biol Chem.
VOL:272 PAGE : 9417-9423 (1997)
[TOP]

[0014]
AUTHOR:Davisson,V. J., Woodside,A. B., Neal, T. R., Stremler, K. E., Muehlbacher, M., and Poulter, C. D.
TITLE:Phosphorylation of isoprenoid alcohols.
JOURNAL:J. Org. Chem.
VOL:51 PAGE : 4768 -4779 (1986)
[TOP]

[0016]
AUTHOR:Ericsson, J., Greene, J. M., Carter, K. C., Shell, B. K., Duan, D. R., Florence, C., and Edwards, P. A.
TITLE:Human geranylgeranyl diphosphate synthase: isolation of the cDNA, chromosomal mapping and tissue expression PubMed ID:9741684
JOURNAL:J Lipid Res.
VOL:39 PAGE : 1731-1739 (1998)
[TOP]

[0026]
AUTHOR:Sagami, H., Matsuoka, S., and Ogura, K.
TITLE:Formation of Z,E,E-geranylgeranyl diphosphate by rat liver microsomes PubMed ID:1995610
JOURNAL:J Biol Chem.
VOL:266 PAGE : 3458-3463 (1991)
[TOP]

[0039]
AUTHOR:Hinson, D. D., Chambliss, K. L., Toth, M. J., Tanaka, R. D., and Gibson, K. M.
TITLE:Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways PubMed ID:9392419
JOURNAL:J Lipid Res.
VOL:38 PAGE : 2216-2223 (1997)
[TOP]

[0064]
AUTHOR:Iimura, O., Vrtovsnik, F., Terzi, F., and Friedlander, G.
TITLE:HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture PubMed ID:9328935
JOURNAL:Kidney Int.
VOL:52 PAGE : 962-972 (1997)
[TOP]

[0070]
AUTHOR:Sagami, H., Korenaga, T., and Ogura, K.
TITLE:Geranylgeranyl diphosphate synthase catalyzing the single condensation between isopentenyl diphosphate and farnesyl diphosphate PubMed ID:8407863
JOURNAL:J Biochem (Tokyo).
VOL:114 PAGE : 118-121 (1993)
[TOP]

[0078]
AUTHOR:Sagami, H., Korenaga, T., Kurisaki, A., and Ogura, K.
TITLE:Biosynthesis of prenyl diphosphates by cell-free extracts from mammalian tissues PubMed ID:8407862
JOURNAL:J Biochem (Tokyo).
VOL:114 PAGE : 112-117 (1993)
[TOP]

[0079]
AUTHOR:Van Dessel, G., De Busser, H., and Lagrou, A.
TITLE:Internalisation of short-chain isoprenyl diphosphates by chromaffin cells from bovine adrenal medulla PubMed ID:9299441
JOURNAL:Biochem Biophys Res Commun.
VOL:238 PAGE : 7-11 (1997)
[TOP]

[0080]
AUTHOR:Sagami, H., Morita, Y., and Ogura, K.
TITLE:Purification and properties of geranylgeranyl-diphosphate synthase from bovine brain PubMed ID:8051156
JOURNAL:J Biol Chem.
VOL:269 PAGE : 20561-20566 (1994)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.