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91356

Sigma-Aldrich

trans,trans-Farnesyl monophosphate ammonium salt

≥95.0% (TLC)

Synonyme(s) :

(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl phosphate ammonium salt, 3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol dihydrogen phosphate ammonium salt, Farnesyl phosphate ammonium salt

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About This Item

Formule empirique (notation de Hill):
C15H27O4P · xNH3
Numéro CAS:
15416-91-8
Poids moléculaire :
302.35 (free acid basis)
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.25

Niveau de qualité

100

Pureté

≥95.0% (TLC)

Forme

powder

Température de stockage

−20°C

InChI

1S/C15H27O4P/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-19-20(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H2,16,17,18)/b14-9-,15-11-

Clé InChI

ALEWCKXBHSDCCT-FBXUGWQNSA-N

Application

Trans, trans-Farnesyl monophosphate (FMP) may be used in studies of potential endogenous modulators of nuclear lysophosphatidic acid (LPA) receptors and in the active site analysis of protein farnesyltransferase(s). Trans,trans-Farnesyl monophosphate may also be used to identify and characterize farnesyl monophosphate kinases.

Actions biochimiques/physiologiques

Farnesyl monophosphate is a metabolite in terpenoid backbone biosynthesis. It was shown to activate PPARalpha and PPARbeta/delta reporter gene expression, indicating new potential roles for the oligoprenyl phosphates as potential endogenous modulators of LPA targets.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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L Thai et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(23), 13080-13085 (1999-11-11)
The ability of Nicotiana tabacum cell cultures to utilize farnesol (F-OH) for sterol and sesquiterpene biosynthesis was investigated. [(3)H]F-OH was readily incorporated into sterols by rapidly growing cell cultures. However, the incorporation rate into sterols was reduced by greater than
Karoly Liliom et al.
Biochimica et biophysica acta, 1761(12), 1506-1514 (2006-11-10)
Oligoprenyl phosphates are key metabolic intermediates for the biosynthesis of steroids, the side chain of ubiquinones, and dolichols and the posttranslational isoprenylation of proteins. Farnesyl phosphates are isoprenoid phosphates that resemble polyunsaturated fatty alcohol phosphates, which we have recently shown
M Bentinger et al.
Archives of biochemistry and biophysics, 353(2), 191-198 (1998-06-02)
As farnesol may serve as a nonsterol endogenous regulator of the mevalonate pathway, the possibility that a kinase specific for its phosphorylation is present in the rat liver was investigated. In the 10,000 g supernatant of rat liver, farnesyl monophosphate
M J Saderholm et al.
Biochemistry, 39(40), 12398-12405 (2000-10-04)
Protein farnesyltransferase catalyzes the posttranslational farnesylation of several proteins involved in signal transduction, including Ras, and is a target enzyme for antitumor therapies. Efficient product formation catalyzed by protein farnesyltransferase requires an enzyme-bound zinc cation and high concentrations of magnesium
I Yoshida et al.
Biochimica et biophysica acta, 995(2), 138-143 (1989-04-06)
Hexaprenyl-diphosphate synthase from Micrococcus luteus B-P 26 has been shown to comprise two essential components, designated as components A and B. Treatment of the synthase with sulphydryl reagents (N-ethylmaleimide, iodoacetamide or p-chloromercuribenzoate) or arginine-specific reagents (2,3-butanedione, 1,2-cyclohexanedione or phenylglyoxal) resulted
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