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G6025

Sigma-Aldrich

Geranylgeranyl pyrophosphate ammonium salt

solution, ≥95% (TLC), ~1 mg/mL in methanol: NH4OH (7:3)

Sinónimos:

GGPP, all trans-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl pyrophosphate ammonium salt

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About This Item

Fórmula empírica (notación de Hill):
C20H36O7P2 · xNH3
Número de CAS:
6699-20-3
Peso molecular:
450.44 (free acid basis)
Número MDL:
MFCD00156114
Código UNSPSC:
12352211
ID de la sustancia en PubChem:
24895243
NACRES:
NA.77

Nivel de calidad

200

Ensayo

≥95% (TLC)

Formulario

solution

envase

vial of 200 μg

concentración

~1 mg/mL in methanol: NH4OH (7:3)

temp. de almacenamiento

−20°C

cadena SMILES

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

InChI

1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/b18-11+,19-13+,20-15+

Clave InChI

OINNEUNVOZHBOX-QIRCYJPOSA-N

Aplicación

Geranylgeranyl pyrophosphate ammonium salt has been used:
  • in the preparation of 2.5X reaction buffer for Rab GGTase assay
  • to add to the culture to further drive Hmg2 degradation
  • as a substrate to carryout in vitro enzymatic assays for the characterization of the prenyltransferases
  • to reverse the action of lovastatin and also used to examine the potential role of GGPP in the study to assess the effects of exposing the melanoma cell lines in the angiogenesis model as a co-culture to lovastatin in vitro

Acciones bioquímicas o fisiológicas

Geranylgeranyl pyrophosphate (GGPP) is a major enzyme that participates in the secondary metabolism of chloroplast. GGPP synthase plays a key role in the biosynthesis of terpenoid. Protein geranylgeranylation, mediated by geranylgeranyl pyrophosphate participates in the development of the ventricular chamber. It also serves as a stage-specific signal to modulate the formation of cardiac cytoarchitecture the time of mid-gestation.
Isoprenoid from the intracellular mevalonate pathway used for prenylation of several low molecular weight G proteins, including Ras. Intermediate in terpene biosynthesis.

Características y beneficios

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Palabra de señalización

Danger

Clasificaciones de peligro

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

Órganos de actuación

Eyes

Código de clase de almacenamiento

3 - Flammable liquids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

51.8 °F - closed cup

Punto de inflamabilidad (°C)

11 °C - closed cup

Equipo de protección personal

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
SLCM6955
SLCL0950
SLCJ7632
SLCH1383
SLCG3802

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Konstantinos Vavitsas et al.
Microbial cell factories, 16(1), 140-140 (2017-08-16)
There are an increasing number of studies regarding genetic manipulation of cyanobacteria to produce commercially interesting compounds. The majority of these works study the expression and optimization of a selected heterologous pathway, largely ignoring the wholeness and complexity of cellular
Christopher I Keeling et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(47), 18838-18843 (2013-10-30)
The mountain pine beetle (Dendroctonus ponderosae Hopkins) is the most destructive pest of western North American pine forests. Adult males produce frontalin, an eight-carbon antiaggregation pheromone, via the mevalonate pathway, as part of several pheromones that initiate and modulate the
Isoprenoid biosynthesis in the diatom Haslea ostrearia
Athanasakoglou A, et al.
The New phytologist (2018)
Sergi Guixé-Muntet et al.
Journal of hepatology, 66(1), 86-94 (2016-08-23)
The transcription factor Krüppel-like factor 2 (KLF2), inducible by simvastatin, confers endothelial vasoprotection. Considering recent data suggesting activation of autophagy by statins, we aimed to: 1) characterize the relationship between autophagy and KLF2 in the endothelium, 2) assess this relationship
Action of Lovastatin (Mevinolin) on an in vitro model of angiogenesis and its co-culture with malignant melanoma cell lines
Depasquale I and Wheatley D N
Cancer Cell International, 6(1), 9-9 (2006)
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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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