Back to HOME

Isoprenoid


DATA No : IIP0005 INFORMANT : Yoshichika Yoshioka

NAME : [2E,6E]-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl diphosphate

COMMON NAME: Farnesyl diphosphate, Farnesyl pyrophosphate
SYMBOL: FPP, FOPP
FORMULA: C15H28O7P2 MOL.WT (average) : 382.326


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). Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected(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 farnesol.(Ref. 0014)
METABOLISM
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). 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 crystal structure of recombinant farnesyl diphosphate synthase has been reported in (Ref. 0017).
The nucleotide sequence of yeast farnesyl diphosphate synthase has been reported in (Ref. 0019). Arabidopsis thaliana contains two differentially expressed farnesyl-diphosphate genes.(Ref. 0038)
NOTE

REFERENCES
[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]

[0017]
AUTHOR:Tarshis, L. C., Yan, M., Poulter, C. D., and Sacchettini, J. C.
TITLE:Crystal structure of recombinant farnesyl diphosphate synthase at 2.6-A resolution PubMed ID:8086404
JOURNAL:Biochemistry.
VOL:33 PAGE : 10871-10877 (1994)
[TOP]

[0019]
AUTHOR:Anderson, M. S., Yarger, J. G., Burck, C. L., and Poulter, C. D.
TITLE:Farnesyl diphosphate synthetase. Molecular cloning, sequence, and expression of an essential gene from Saccharomyces cerevisiae PubMed ID:2681213
JOURNAL:J Biol Chem.
VOL:264 PAGE : 19176-19184 (1989)
[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]

[0038]
AUTHOR:de Ropp, J. S., and Troy, F. A.
TITLE:2H NMR investigation of the organization and dynamics of polyisoprenols in membranes PubMed ID:4066690
JOURNAL:J Biol Chem.
VOL:260 PAGE : 15669-15674 (1985)
[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]

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