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91356

Sigma-Aldrich

trans,trans-Farnesyl monophosphate ammonium salt

≥95.0% (TLC)

Synonym(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

Empirical Formula (Hill Notation):
C15H27O4P · xNH3
CAS Number:
15416-91-8
Molecular Weight:
302.35 (free acid basis)
UNSPSC Code:
12352200
NACRES:
NA.25

Assay

≥95.0% (TLC)

form

powder

storage temp.

−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-

InChI key

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.

Biochem/physiol Actions

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Jennifer S Pickett et al.
Biochemistry, 42(32), 9741-9748 (2003-08-13)
The zinc metalloenzyme protein farnesyltransferase (FTase) catalyzes the transfer of a 15-carbon farnesyl moiety from farnesyl diphosphate (FPP) to a cysteine residue near the C-terminus of a protein substrate. Several crystal structures of inactive FTase.FPP.peptide complexes indicate that K164alpha interacts
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