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44270

Sigma-Aldrich

trans,trans-Farnesyl pyrophosphate ammonium salt

≥95.0% (HPLC)

Synonym(s):

(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl pyrophosphate ammonium salt, Farnesyl diphosphate ammonium salt

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About This Item

Empirical Formula (Hill Notation):
C15H28O7P2 · xNH3
Molecular Weight:
382.33 (free acid basis)
Beilstein/REAXYS Number:
2482197
UNSPSC Code:
12352212
PubChem Substance ID:
329756482
NACRES:
NA.25

assay

≥95.0% (HPLC)

form

solid

storage temp.

−20°C

SMILES string

N.C\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

InChI

1S/C15H28O7P2.H3N/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18;/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18);1H3/b14-9+,15-11+;

InChI key

CPYJTMLHKIWGDF-NDHHSALASA-N

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Application

Farnesyl diphosphate ammonium salt may be used to study the posttranslational process known as farnesylation that is used to modify important proteins such as the Ras oncogene.

Biochem/physiol Actions

Farnesyl pyrophosphate is a key intermediate in the biosynthesis of more complex sesquiterpenoids, higher terpenoids, and steroids and different biological functions have been discovered for FPP and the corresponding alcohol farnesol. FPP plays an important role in the posttranslational processing of Ras proteins. Mutated forms of Ras are associated with human cancer and are therefore investigated in cancer research.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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S M Sebti et al.
Oncogene, 19(56), 6584-6593 (2001-06-28)
In 1990, more than 10 years after the discovery that the low molecular weight GTPase Ras is a major contributor to human cancer, farnesylation, a lipid posttranslational modification required for the cancer-causing activity of Ras, emerged as a major target
Farnesyl Diphosphate Analogues with Aryl Moieties Are Efficient Alternate Substrates for Protein Farnesyltransferase.
Subramanian T, Pais JE, Liu S, et al.
Biochemistry (2012)
Po-Huang Liang et al.
European journal of biochemistry, 269(14), 3339-3354 (2002-07-24)
In this review, we summarize recent progress in studying three main classes of prenyltransferases: (a) isoprenyl pyrophosphate synthases (IPPSs), which catalyze chain elongation of allylic pyrophosphate substrates via consecutive condensation reactions with isopentenyl pyrophosphate (IPP) to generate linear polymers with
Roman Shchepin et al.
Chemistry & biology, 10(8), 743-750 (2003-09-05)
The dimorphic fungus Candida albicans produces extracellular farnesol (3,7,11-trimethyl-2,6,10-dodecatriene-1-ol) which acts as a quorum-sensing molecule (QSM) to suppress filamentation. Of four possible geometric isomers of farnesol, only the E,E isomer possesses QSM activity. We tested 40 natural and synthetic analogs
R J Hohl et al.
Lipids, 33(1), 39-46 (1998-02-21)
This investigation compares the effects of three farnesyl pyrophosphate analogs on selected aspects of isoprenoid metabolism. E,E-alpha-Hydroxyfarnesylphosphonate was prepared by an improved variation on a literature synthesis, which also gave access to the new Z,E-alpha-hydroxyfarnesyl- and alpha-hydroxygeranylphosphonates. A striking find
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