Geranylgeranyl diphosphate

Base Information

• Chemical Name: Geranylgeranyl diphosphate
• CAS No.: 6699-20-3
• Molecular Formula: C₂₀H₃₆O₇P₂
• Molecular Weight: 450.449
• Hs Code.: 35079090
• UNII: N21T0D88LX
• DSSTox Substance ID: DTXSID90863929
• Nikkaji Number: J39.582J
• Wikipedia: Geranylgeranyl_pyrophosphate
• Wikidata: Q774795
• Pharos Ligand ID: RQZQKCBZ91UR
• Metabolomics Workbench ID: 28459
• ChEMBL ID: CHEMBL1229266
• Mol file: 6699-20-3.mol

Synonyms:geranylgeraniol diphosphate;geranylgeranyl diphosphate;geranylgeranyl pyrophosphate;geranylgeranyl pyrophosphate, (Z,E,E)-isomer;geranylgeranyl pyrophosphate, 14C-labeled, (E,E,E)-isomer;GGPP cpd;GGPP diphosphate;nerylneryl diphosphate

Chemical Property of Geranylgeranyl diphosphate

Chemical Property:

• Appearance/Colour: solution
• Vapor Pressure: 3.7E-15mmHg at 25°C
• Boiling Point: 584.1 °C at 760 mmHg
• PKA: 1.04±0.50(Predicted)
• Flash Point: 307 °C
• PSA: 138.57000
• Density: 1.167 g/cm³
• LogP: 7.98720
• Storage Temp.: −20°C
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 14
• Exact Mass: 450.19362748
• Heavy Atom Count: 29
• Complexity: 710

Purity/Quality:

98%,99%, ^*data from raw suppliers

Geranylgeranyl pyrophosphate triammonium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): FT
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC(=CCOP(=O)(O)OP(=O)(O)O)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C(=C/COP(=O)(O)OP(=O)(O)O)/C)/C)/C)C
• Description: Geranylgeranyl pyrophosphate (GGPP) is a potent endogenous regulator of Hmg2p degradation.This work was launched by the unexpected observation that GGPP addition directly to living yeast cultures caused high potency and specific stimulation of Hmg2p degradation. This effect of GGPP was not recapitulated by FPP,GGOH, or related isoprenoids. GGPP-caused Hmg2p degradation met all the criteria for the previously characterized endogenous signal.The action of added GGPP did not require production of endogenous sterol molecules, indicating that it did not act by causing the build-up of an endogenouspathway signal.
• Uses: Geranylgeranyl pyrophosphate ammonium salt has been used:in the preparation of 2.5X reaction buffer for Rab GGTase assayto add to the culture to further drive Hmg2 degradationas a substrate to carryout in vitro enzymatic assays for the characterization of the prenyltransferasesto 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

Technology Process of Geranylgeranyl diphosphate

There total 3 articles about Geranylgeranyl diphosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

isopentyl pyrophosphate (358-71-4) + geranyl diphosphate (763-10-0) → (E,E,E)-geranylgeranyl diphosphate (6699-20-3,13100-78-2,64732-91-8) + farnesyl pyrophosphate (372-97-4,13058-04-3,25744-33-6,27248-37-9,27248-38-0,40716-68-5)

Guidance literature:

With Homo sapiens geranylgeranyl diphosphate synthase; 2-hydroxyethanethiol; magnesium chloride; In aq. buffer; at 37 ℃; for 6h; Enzymatic reaction;

DOI:10.1016/j.molcatb.2015.07.006

Reference yield:

isopentyl pyrophosphate (358-71-4) + geranyl diphosphate (763-10-0) → (E,E,E)-geranylgeranyl diphosphate (6699-20-3,13100-78-2,64732-91-8) + farnesylgeranyl diphosphate

Guidance literature:

With Phomopsis amygdali Niigata-2 prenyltransferase amyG, recombinant; magnesium(II); In aq. buffer; at 30 ℃; pH=8; Enzymatic reaction;

DOI:10.1080/09168451.2014.882759

Reference yield:

geranyl diphosphate (763-10-0) → (E,E,E)-geranylgeranyl diphosphate (6699-20-3,13100-78-2,64732-91-8)

Guidance literature:

With recombinant PaPS C₃₉₈ mutant (position 328 -725), 44 kDa; Enzymatic reaction;

DOI:10.1021/jo802319e

upstream raw materials:

geranyl diphosphate

isopentyl pyrophosphate

Downstream raw materials:

ent-copalyl diphosphate

cis-abienol

8,15-dihydroxy-13E-labdane

labd-13E-en-8α,15-diol diphosphate

Refernces

• 1、 Liu, Chengwei,Noike, Motoyoshi,Minami, Atsushi,Oikawa, Hideaki,Dairi, Tohru. "A fungal prenyltransferase catalyzes the regular di-prenylation at positions 20 and 21 of paxilline". . p. 448 - 454. Retrieved 2015/07/27.