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Key Documents

810811P

Avanti

18:1 DGPP

dioleoylglycerol pyrophosphate (ammonium salt), powder

Synonyme(s) :

110744

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About This Item

Formule empirique (notation de Hill):
C39H80N2O11P2
Numéro CAS:
Poids moléculaire :
815.01
Code UNSPSC :
12352211
Nomenclature NACRES :
NA.25

Pureté

>99% (TLC)

Forme

powder

Conditionnement

pkg of 1 × 5 mg (810811P-5mg)

Fabricant/nom de marque

Avanti Research - A Croda Brand 810811P

Type de lipide

bioactive lipids

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

[O-]P(OC[C@]([H])(OC(CCCCCCC/C=C\CCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)(OP([O-])(O)=O)=O.[NH4+].[NH4+]

InChI

1S/C39H74O11P2.2H3N/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)47-35-37(36-48-52(45,46)50-51(42,43)44)49-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;;/h17-20,37H,3-16,21-36H2,1-2H3,(H,45,46)(H2,42,43,44);2*1H3/b19-17-,20-18-;;/t37-;;/m1../s1

Clé InChI

SIWIEYLZDXPRIY-AXQFFRRZSA-N

Description générale

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
Dioleoylglycerophosphate (DGPP) is mainly present in plants and yeast. It carries two phosphate groups in its headgroup. DGPP 18:1 (dioleoylglycerol pyrophosphate) has two oleyl chains and is a bioactive lipid.

Application

DGPP 18:1 (dioleoylglycerol pyrophosphate) may be used in biochemical assays to study its effects on transient receptor potential 1 (TRPV1) function. It may also be used in liposome binding studies.

Actions biochimiques/physiologiques

Dioleoylglycerophosphate (DGPP) is capable of stimulating stress-related responses in plants. It may also play a role in abscisic acid (ABA) signaling.

Conditionnement

5 mL Clear Glass Sealed Ampule (810811P-5mg)

Informations légales

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

No data available

Point d'éclair (°C)

No data available


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Priya Putta et al.
Chemistry and physics of lipids, 231, 104919-104919 (2020-05-18)
Epsin-like Clathrin Adaptor 1 (ECA1/ PICALM1A) is an A/ENTH domain protein that acts as an adaptor protein in clathrin-mediated endocytosis. ECA1 is recruited to the membrane during salt stress signaling in plants in a phosphatidic acid (PA)-dependent manner. PA is
Liza Strawn et al.
Frontiers in plant science, 3, 40-40 (2012-05-31)
Phosphatidic acid (PA) is a lipid second messenger that is formed transiently in plants in response to different stress conditions, and plays a role in recruiting protein targets, ultimately enabling an adequate response. Intriguingly, this increase in PA concentration in
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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