6699-20-3 Usage
Description
3,7,11,15-TETRAMETHYL-2,6,10,14-HEXADECATETRAENYL PYROPHOSPHATE AMMONIUM SALT, also known as Geranylgeranyl pyrophosphate (GGPP) ammonium salt, is a potent endogenous regulator of Hmg2p degradation. It is an isoprenoid compound that has been observed to stimulate Hmg2p degradation specifically and potently when added directly to living yeast cultures. This effect is unique to GGPP and is not replicated by other related isoprenoids such as FPP, GGOH, or similar compounds. The action of GGPP does not require the production of endogenous sterol molecules, indicating that it does not act by causing the build-up of an endogenous pathway signal.
Uses
Used in Biochemical Research:
3,7,11,15-TETRAMETHYL-2,6,10,14-HEXADECATETRAENYL PYROPHOSPHATE AMMONIUM SALT is used as a substrate in biochemical research for the characterization of prenyltransferases. It aids in understanding the enzymatic mechanisms and functions of these enzymes in various biological processes.
Used in Rab GGTase Assay:
In the field of molecular biology, 3,7,11,15-TETRAMETHYL-2,6,10,14-HEXADECATETRAENYL PYROPHOSPHATE AMMONIUM SALT is used in the preparation of 2.5X reaction buffer for Rab GGTase assay. This application helps in studying the geranylgeranylation process, which is crucial for the function of Rab proteins in cellular membrane trafficking.
Used in Yeast Cultures:
3,7,11,15-TETRAMETHYL-2,6,10,14-HEXADECATETRAENYL PYROPHOSPHATE AMMONIUM SALT is used in yeast cultures to further drive Hmg2 degradation. This application is valuable for investigating the regulatory mechanisms of Hmg2p and its role in cellular processes.
Used in Angiogenesis Model:
In the study of angiogenesis, 3,7,11,15-TETRAMETHYL-2,6,10,14-HEXADECATETRAENYL PYROPHOSPHATE AMMONIUM SALT is used to assess the effects of exposing melanoma cell lines to the angiogenesis model as a co-culture to lovastatin. This helps in understanding the potential role of GGPP in modulating the activity of lovastatin and its impact on angiogenesis.
Used as a Reversal Agent:
3,7,11,15-TETRAMETHYL-2,6,10,14-HEXADECATETRAENYL PYROPHOSPHATE AMMONIUM SALT is used to reverse the action of lovastatin, a cholesterol-lowering drug. This application is important for studying the interactions between GGPP and lovastatin, and their combined effects on cholesterol biosynthesis and other related pathways.
Biosynthesis
Biosynthesis of geranylgeranyl pyrophosphate. Geranylgeranyl pyrophosphate can be synthesized from isopentenyl pyrophosphate through two prenyl transferases, FPP-synthase and GGPP-synthase (left) or through one prenyl transferase, GGPP-synthase (right). Abbreviations: DMAPP (dimethylallyl pyrophosphate), IPP (isopentenyl pyrophosphate), GPP (geranyl pyrophosphate), FPP (farnesyl pyrophosphate) and GGPP (geranylgeranyl pyrophosphate)
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.
Purification Methods
Purify the pyrophosphate by countercurrent distribution between two phases of a butanol/isopropyl ether/ammonia/water mixture (15:5:1:19) (v/v), or by chromatography on DEAE-cellulose (linear gradient of 0.02M KCl in 1mM Tris buffer, pH 8.9). Alternatively purify it through a column of Dowex 1-x8 (formate form previously washed with MeOH) and eluted with a linear gradient of 0.053—0.43M ammonium formate in a total volume of 300mL of MeOH. The purity can be checked by TLC on Silica gel G on buffered plates (pH 6.5), eluted with CHCl3/MeOH/H2O (60:40:9) and developed with I2 vapour. Store it as a powder at 0o. [Altman et al. J Am Chem Soc 94 3257 1972.] Itis more stable as the di(tri-n-butylammonium)hydrogen phosphate salt which can be obtained from the acid by evaporation in a rotary evaporator below 32o [Upper & West J Biol Chem 242 3285 1967]. [Gregonis & Rilling Biochemistry 13 1538 1974, Gregonis & Rilling Biochem Biophys Res Commun 54 449 1973.]
Check Digit Verification of cas no
The CAS Registry Mumber 6699-20-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,6,9 and 9 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 6699-20:
(6*6)+(5*6)+(4*9)+(3*9)+(2*2)+(1*0)=133
133 % 10 = 3
So 6699-20-3 is a valid CAS Registry Number.
InChI:InChI=1/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+
6699-20-3Relevant articles and documents
Specificity of geranylgeranyl diphosphate synthase for homoallylic substrate analogs
Ohya, Norimasa,Ichijo, Takumi,Sato, Hana,Nakamura, Takeshi,Yokota, Saki,Sagami, Hiroshi,Nagaki, Masahiko
, p. 179 - 182 (2015/09/01)
The goal of this study was to determine the substrate specificity of Homo sapiens geranylgeranyl diphosphate synthase (GGPPase) for analogs of isopentenyl diphosphate (IPP) to facilitate the application to organic synthesis techniques to the study of prenyl chain elongation enzymes. For this purpose, we used the IPP analogs 2a-d, which contain different alkyl side-chains at the 3-position, as substrates of the condensation reaction with the allylic substrate geranyl diphosphate (GPP) that is catalyzed by GGPPase. GGPPase catalyzed the reaction of GPP with 3-desmethylisopentenyl diphosphate (but-3-enyl diphosphate) to yield 3-desmethylfarnesyl diphosphate (12.1%), as well as the reaction of GPP with 3-ethylbut-3-enyl diphosphate or 3-propylbut-3-enyl diphosphate to yield 3-ethylfarnesyl diphosphate (46.9%) or 3-propylfarnesyl diphosphate (22.6%), respectively. However, a reaction product was not detected when 3-butylbut-3-enyl diphosphate was used as substrate.
Biosynthetic gene-based secondary metabolite screening: A new diterpene, methyl phomopsenonate, from the fungus Phomopsis amygdali
Toyomasu, Tomonobu,Kaneko, Akane,Tokiwano, Tetsuo,Kanno, Yuya,Kanno, Yuri,Niida, Rie,Miura, Shigeyoshi,Nishioka, Taiki,Ikeda, Chiho,Mitsuhashi, Wataru,Dairi, Tohru,Kawano, Tomikazu,Oikawa, Hideaki,Kato, Nobuo,Sassa, Takeshi
body text, p. 1541 - 1548 (2009/10/02)
The presence of the geranylgeranyl diphosphate synthase (GGS) gene is a common feature of gene clusters for diterpene biosynthesis. We demonstrated identification of a diterpene gene cluster using homology- based PCR of GGS genes and the subsequent genome
