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About This Item
Empirical Formula (Hill Notation):
C19H44N2O11P2
CAS Number:
Molecular Weight:
538.51
UNSPSC Code:
12352211
NACRES:
NA.25
Product Name
08:0 DGPP, Avanti Research™ - A Croda Brand 810800P, powder
SMILES string
[O-]P(OC[C@]([H])(OC(CCCCCCC)=O)COC(CCCCCCC)=O)(OP([O-])(O)=O)=O.[NH4+].[NH4+]
InChI
1S/C19H38O11P2.2H3N/c1-3-5-7-9-11-13-18(20)27-15-17(16-28-32(25,26)30-31(22,23)24)29-19(21)14-12-10-8-6-4-2;;/h17H,3-16H2,1-2H3,(H,25,26)(H2,22,23,24);2*1H3/t17-;;/m1../s1
InChI key
XNPNJXYONHGAON-ZEECNFPPSA-N
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 10 mg (810800P-10mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 810800P
shipped in
dry ice
storage temp.
−20°C
Biochem/physiol Actions
Diacylglycerol pyrophosphate (DGPP) can decrease the phosphatidic acid (PA) signal and can acts as a signaling lipid.
General description
Diacylglycerol pyrophosphate (DGPP), a phospholipid that is usually seen in plants and yeast. It is formed during phosphorylation of phosphatidic acid (PA) with the help of PA kinase (PAK). It is an anionic phospholipid with a pyrophosphate group attached to diacylglycerol.
Diacylglycerol pyrophosphate (DGPP), involved in a novel signaling pathway, has been found in plants, Saccharomyces cerevisiae, and Escherichia coli and macrophage-activating factor, and suggests a potential role for this compound in triggering homeostatic cellular responses.Biological Applications: Short chain DGPP (DiC8) DiC8 DGPP is added to a test tube as a chloroform solution and the solvent is removed. Add water or buffer to the dry lipid residue followed by sonication. The solution is added to cells directly. The short chain DGPP is taken up by mammalian cells and by yeast. Long chain DGPP (DiC18:1) DiC18:1 DGPP is added to a test tube as a chloroform solution and the solvent is removed. Add 0.5% Tergitol (detergent) solution and add this to cells.Notes:Biological Application — "I am not sure how well the long chain DGPP is taken up in yeast cells, that is why we synthesized the DiC8 compound. We only use the long chain compound as a standard for TLC, HPLC and for DGPP phosphatase assays".Storage Conditions — "Store concentrated, ~25mg/ml in chloroform. Concentrations below 10mg/ml are not as stable".Personal communication, George M. Carman, Sept. 1999
Packaging
5 mL Clear Glass Sealed Ampule (810800P-10mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class
11 - Combustible Solids
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Zn2+-dependent surface behavior of diacylglycerol pyrophosphate and its mixtures with phosphatidic acid at different pHs
Villasuso AL, et al.
Frontiers in Plant Science, 5, 371-371 (2014)
Signalling diacylglycerol pyrophosphate, a new phosphatidic acid metabolite
Van SB, et al.
Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids, 1761(2), 151-159 (2006)
Bas van Schooten et al.
Biochimica et biophysica acta, 1761(2), 151-159 (2006-02-14)
Diacylglycerol pyrophosphate (DGPP) is a novel phospholipid that has been found in plants and yeast but not in higher animals. It is produced through phosphorylation of phosphatidic acid (PA) by the novel enzyme PA kinase (PAK). In plants, DGPP is
M A Balboa et al.
The Journal of biological chemistry, 274(1), 522-526 (1998-12-29)
We have found that the novel phospholipid diacylglycerol pyrophosphate (DGPP), identified in bacteria, yeast, and plants, but not in mammalian cells, is able to potently activate macrophages for enhanced secretion of arachidonate metabolites, a key event in the immunoinflammatory response
T Munnik et al.
The Journal of biological chemistry, 271(26), 15708-15715 (1996-06-28)
We provide evidence that phosphatidic acid (PtdOH) formed during signaling in plants is metabolized by a novel pathway. In much of this study, 32Pi-labeled Chlamydomonas cells were used, and signaling was activated by adding the G-protein activator mastoparan. Within seconds
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