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44270

Sigma-Aldrich

trans,trans-Farnesyl pyrophosphate ammonium salt

≥95.0% (HPLC)

Sinônimo(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

Fórmula empírica (Notação de Hill):
C15H28O7P2 · xNH3
Peso molecular:
382.33 (free acid basis)
Beilstein:
2482197
Código UNSPSC:
12352212
ID de substância PubChem:
NACRES:
NA.25

grau

for analytical purposes

Ensaio

≥95.0% (HPLC)

Formulário

solid

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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+;

chave InChI

CPYJTMLHKIWGDF-NDHHSALASA-N

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Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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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
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)
Norbert Berndt et al.
Nature protocols, 6(11), 1775-1791 (2011-11-01)
The importance of the post-translational lipid modifications farnesylation and geranylgeranylation in protein localization and function coupled with the critical role of prenylated proteins in malignant transformation has prompted interest in their biology and the development of farnesyl transferase and geranylgeranyl
H Xie et al.
The Journal of organic chemistry, 65(25), 8552-8563 (2000-12-12)
The a-factor of Saccharomyces cerevisiae is a dodecapeptide pheromone (YIIKGVFWDPAC(Farnesyl)-OCH(3), 1), in which post-translational modification with a farnesyl isoprenoid and carboxymethyl group is required for full biological activity. This peptide has been used as a model system to explore the

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