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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:
Molecular Weight:
450.44 (free acid basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
G6772F689269579
vibrant-m

G6772

Geranyl pyrophosphate ammonium salt

form

solution

form

liquid

form

methanol:ammonia solution

form

powder

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

packaging

vial of 200 μg

packaging

vial of 200 μg

packaging

vial of 200 μg

packaging

-

concentration

~1 mg/mL in methanol: NH4OH (7:3)

concentration

1 mg/mL in methanol (:aqueous 10 mM NH4OH (7:3))

concentration

-

concentration

-

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.

signalword

Danger

Hazard Classifications

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

target_organs

Eyes

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

51.8 °F - closed cup

flash_point_c

11 °C - closed cup

ppe

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


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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
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
Introduction of the archaebacterial geranylgeranyl pyrophosphate synthase gene into Chlamydomonas reinhardtii chloroplast
Fukusaki E I, et al.
Journal of Bioscience and Bioengineering, 95(3), 283-287 (2003)
Kosuke Tanaka et al.
Cancer letters, 385, 215-224 (2016-10-30)
Malignant mesothelioma (MM) frequently exhibits Hippo signaling pathway inactivation (HPI) mainly due to NF2 and/or LATS2 mutations, which leads to the activation of YAP transcriptional co-activator. Here, we show antitumor effects of statin on MM cells with HPI, through the

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