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G6025

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)
NACRES:
NA.77
PubChem Substance ID:
24895243
UNSPSC Code:
12352211
MDL number:
MFCD00156114
Assay:
≥95% (TLC)
Form:
solution
Quality level:
200
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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
  • 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.

Disclaimer

Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.

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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

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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Articles

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

고리형 뉴클레오타이드를 위한 생체 활성 저분자

고리형 AMP(cAMP), 고리형 GMP(cGMP), 고리형 ADP-리보스를 포함하여 고리형 뉴클레오타이드는 GPCR 활성화에 의해 개시된 세포내 이벤트의 2차 전달자로서 광범위하게 연구되었습니다. cAMP는 주로 cAMP 의존성 단백질 인산화효소(PKA)의 활성화를 통해 모든 진핵생물 세포에서 세포 기능을 변형시키지만 cAMP 개폐 이온 채널 및 cAMP에 의해 직접 활성화되는 구아닌 뉴클레오타이드 교환 인자를 통해서도 변형시킵니다.