Isoprenoid

DATA No : IIP0003 INFORMANT : Yoshichika Yoshioka

NAME : [2E]-3,7-Dimethyl-2,6-octadien-1-yl diphosphate

COMMON NAME	:	Geranyl diphosphate, Geranyl pyrophosphate
SYMBOL	:	GOPP, GPP
FORMULA	:	C₁₀H₂₀O₇P₂ MOL.WT (average) : 314.209

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BIOLOGICAL ACTIVITY

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).

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CHEMICAL SYNTHESIS

The compound can be synthesized from geraniol.(Ref. 0014)

METABOLISM

The product formed by the action of geranyl diphosphate synthase and the first intermediate product by the action of farnesyl diphosphate synthase from dimethylallyl diphosphate and isopentenyl diphosphate. The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capacity was as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors(Ref. 0039).

GENETIC INFORMATION

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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)

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[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)

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[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)

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