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G6025

Sigma-Aldrich

Geranylgeranyl pyrophosphate ammonium salt

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

Synonym(s):

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

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About This Item

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
Pricing and availability is not currently available.

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

Application

Geranylgeranyl pyrophosphate ammonium salt has been used:
  • in the preparation of 2.5X reaction buffer for Rab GGTase assay[1]
  • to add to the culture to further drive Hmg2 degradation[2]
  • as a substrate to carryout in vitro enzymatic assays for the characterization of the prenyltransferases[3]
  • 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[4]

Biochem/physiol Actions

Geranylgeranyl pyrophosphate (GGPP) is a major enzyme that participates in the secondary metabolism of chloroplast.[5] 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.[6]
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

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

51.8 °F - closed cup

Flash Point(C)

11 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000413003
0000413005
0000413005
0000413003
0000392020

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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
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
Prenylation assays for small GTPases
Transmembrane signaling protocols, 251-260 (1998)
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)
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Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. How can the molarity of Geranylgeranyl pyrophosphate ammonium salt, G6025, be calculated?

    1 answer

    1. The product is a 1 mg/mL (2.5 mM) solution of geranylgeranyl pyrophosphate in a 7:3 mixture of methanol and 10 mM ammonium hydroxide. Additionally, the solution is 2 mM in ammonium bicarbonate. It is important to note that this is a triammonium salt of geranylgeranyl pyrophosphate and has a molecular weight of 501.

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