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G6025

Sigma-Aldrich

Geranylgeranyl pyrophosphate ammonium salt

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

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Synonym(s):
GGPP, all trans-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenyl pyrophosphate ammonium salt
Empirical Formula (Hill Notation):
C20H36O7P2 · xNH3
CAS Number:
6699-20-3
Molecular Weight:
450.44 (free acid basis)
MDL number:
MFCD00156114
UNSPSC Code:
12352211
PubChem Substance ID:
24895243
NACRES:
NA.77

Quality Level

200

Assay

≥95% (TLC)

form

solution

packaging

vial of 200 μg

concentration

~1 mg/mL in methanol: NH4OH (7:3)

storage temp.

−20°C

SMILES string

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+

InChI key

OINNEUNVOZHBOX-QIRCYJPOSA-N

Related Categories

Application

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

Biochem/physiol Actions

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.

Features and Benefits

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.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Eyes

WGK

WGK 2

Flash Point(F)

51.8 °F

Flash Point(C)

11 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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Prenylation assays for small GTPases
Transmembrane signaling protocols, 251-260 (1998)
Irakli Loladze et al.
Molecular nutrition & food research, 63(15), e1801047-e1801047 (2019-06-30)
Plant and human tissues (e.g., leaves, retina) share the need for carotenoids to protect against light-induced and other oxidative stresses. While plants synthesize carotenoids de novo, humans must obtain them primarily through plant-based foods. In plants, elevated levels of atmospheric
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)
Hirokazu Sakamoto et al.
The Journal of eukaryotic microbiology, 64(4), 440-446 (2016-11-05)
Some organisms have retained plastids even after they have lost the ability to photosynthesize. Several studies of nonphotosynthetic plastids in apicomplexan parasites have shown that the isopentenyl pyrophosphate biosynthesis pathway in the organelle is essential for their survival. A phytohormone
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