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F6892

Sigma-Aldrich

Farnesyl pyrophosphate ammonium salt

methanol:ammonia solution, ≥95% (TLC)

Synonim(y):

3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl pyrophosphate ammonium salt, FPP

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About This Item

Wzór empiryczny (zapis Hilla):
C15H37N3O7P2
Numer CAS:
13058-04-3
Masa cząsteczkowa:
433.42
Numer MDL:
MFCD00189688
Kod UNSPSC:
12352204
Identyfikator substancji w PubChem:
24894923
NACRES:
NA.83

Próba

≥95% (TLC)

Postać

methanol:ammonia solution

opakowanie

vial of 200 μg

temp. przechowywania

−20°C

ciąg SMILES

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

InChI

1S/C15H28O7P2/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)/b14-9+,15-11+

Klucz InChI

VWFJDQUYCIWHTN-YFVJMOTDSA-N

informacje o genach

rat ... Fnta(25318)

Opis ogólny

Farnesyl pyrophosphate is a 15-carbon isoprenoid synthesized from geranyl pyrophosphate (GPP) by the action of enzyme farnesyl pyrophosphate synthase (FPPS).

Zastosowanie

Farnesyl pyrophosphate ammonium salt has been used:
  • as a prenylation agonist in human osteogenic sarcoma cells in collagen-based cell invasion assays
  • in the prenylation of the hepatocyte growth factor (HGF) in human umbilical vein endothelial cells (HUVECs)
  • as a substrate in prenyltransferases assay in diatom Haslea ostrearia

Działania biochem./fizjol.

Farnesyl pyrophosphate (FPP) is the precursor for the biosynthesis of cholesterol, ubiquinone and dolicol. It is part of the intracellular mevalonate pathway. FPP is essential for cell survival and is used for prenylation of several low molecular mass G proteins, including Ras. Inhibition of prenylation results in loss of oncogenic potential of Ras proteins. Inhibition of prenylation may serve as therapeutic potential for management of synaptic plasticity and Alzheimer′s disease.

Postać fizyczna

Solution in methanol: 10mM aqueous NH4OH (7:3)
Actual concentration given on label
This page may contain text that has been machine translated.

Hasło ostrzegawcze

Danger

Zwroty wskazujące rodzaj zagrożenia

H225,H301 + H311 + H331,H315,H319,H370,H412

Klasyfikacja zagrożeń

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 1

Organy docelowe

Eyes,Central nervous system

Kod klasy składowania

3 - Flammable liquids

Klasa zagrożenia wodnego (WGK)

WGK 2

Temperatura zapłonu (°F)

60.8 °F

Temperatura zapłonu (°C)

16 °C

Certyfikaty analizy (CoA)

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Odwiedź Bibliotekę dokumentów

Protein prenylation and synaptic plasticity: implications for Alzheimer?s disease
Hottman DA and Li L
Molecular Neurobiology, 50(1), 177-185 (2014)
John M Sanders et al.
Journal of medicinal chemistry, 48(8), 2957-2963 (2005-04-15)
We report the design, synthesis and testing of a series of novel bisphosphonates, pyridinium-1-yl-hydroxy-bisphosphonates, based on the results of comparative molecular similarity indices analysis and pharmacophore modeling studies of farnesyl diphosphate synthase (FPPS) inhibition, human Vgamma2Vdelta2 T cell activation and
Structural characterization of substrate and inhibitor binding to farnesyl pyrophosphate synthase from Pseudomonas aeruginosa
Schmidberger JW, et al.
Acta Crystallographica Section D, Biological Crystallography, 71(3), 721-731 (2015)
Protein prenylation: enzymes, therapeutics, and biotechnology applications
Palsuledesai CC and Distefano MD
ACS Chemical Biology, 10(1), 51-62 (2014)
Chantal Brämer et al.
Biotechnology progress, 35(4), e2812-e2812 (2019-04-02)
The natural production of patchouli oil in developing countries cannot meet the increasing demand any more. This leads to socioecological consequences, such as the use of arable land, which is actually intended for food. Hence, the world market price increased
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Produkty

Cholesterol Biosynthesis

Biosynthesis of cholesterol generally takes place in the endoplasmic reticulum of hepatic cells and begins with acetyl- CoA, which is mainly derived from an oxidation reaction in the mitochondria. Acetyl-CoA and acetoacetyl-CoA are converted to 3-hydroxy- 3-methylglutaryl-CoA (HMG-CoA) by HMG-CoA synthase.

Dietary Terpenes

Terpenes comprise the largest and most diverse class of secondary metabolites; approximately 55,000 compounds have been identified to date.

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