810811 | 18:1 DGPP

dioleoylglycerol pyrophosphate (ammonium salt)

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18:1 DGPP

18:1 DGPP

dioleoylglycerol pyrophosphate (ammonium salt)

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

Hygroscopic
No
Light Sensitive
No
Molecular Formula
C39H80N2O11P2
Percent Composition
C 57.47%, H 9.89%, N 3.44%, O 21.59%, P 7.60%
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
474943-14-1
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
815.007
Exact Mass
814.524
Synonyms
110744

van Schooten B, Testerink C, Munnik T. Signalling diacylglycerol pyrophosphate, a new phosphatidic acid metabolite. Biochim Biophys Acta. 2006 Feb;1761(2):151-9. doi: 10.1016/j.bbalip.2005.12.010. Epub 2006 Jan 23. PMID: 16469533.

 PubMed ID: 16469533

Oshiro J, Han GS, Carman GM. Diacylglycerol pyrophosphate phosphatase in Saccharomyces cerevisiae. Biochim Biophys Acta. 2003 Nov 30;1635(1):1-9. doi: 10.1016/j.bbalip.2003.10.002. PMID: 14642771.

 PubMed ID: 14642771

Balboa MA, Balsinde J, Dillon DA, Carman GM, Dennis EA. Proinflammatory macrophage-activating properties of the novel phospholipid diacylglycerol pyrophosphate. J Biol Chem. 1999 Jan 1;274(1):522-6. doi: 10.1074/jbc.274.1.522. PMID: 9867874.

 PubMed ID: 9867874

Toke DA, Bennett WL, Dillon DA, Wu WI, Chen X, Ostrander DB, Oshiro J, Cremesti A, Voelker DR, Fischl AS, Carman GM. Isolation and characterization of the Saccharomyces cerevisiae DPP1 gene encoding diacylglycerol pyrophosphate phosphatase. J Biol Chem. 1998 Feb 6;273(6):3278-84. doi: 10.1074/jbc.273.6.3278. PMID: 9452443.

 PubMed ID: 9452443

Carman GM. Phosphatidate phosphatases and diacylglycerol pyrophosphate phosphatases in Saccharomyces cerevisiae and Escherichia coli. Biochim Biophys Acta. 1997 Sep 4;1348(1-2):45-55. doi: 10.1016/s0005-2760(97)00095-7. PMID: 9370315.

 PubMed ID: 9370315

Munnik T, de Vrije T, Irvine RF, Musgrave A. Identification of diacylglycerol pyrophosphate as a novel metabolic product of phosphatidic acid during G-protein activation in plants. J Biol Chem. 1996 Jun 28;271(26):15708-15. doi: 10.1074/jbc.271.26.15708. PMID: 8663116.

 PubMed ID: 8663116