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Merck
CN

810811P

Avanti

18:1 DGPP

dioleoylglycerol pyrophosphate (ammonium salt), powder

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别名:
110744
经验公式(希尔记法):
C39H80N2O11P2
分子量:
815.01
UNSPSC代码:
12352211
NACRES:
NA.25

检测方案

>99% (TLC)

形式

powder

包装

pkg of 1 × 5 mg (810811P-5mg)

制造商/商品名称

Avanti Polar Lipids 810811P

脂质类型

bioactive lipids

运输

dry ice

储存温度

−20°C

SMILES字符串

[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

InChI key

SIWIEYLZDXPRIY-AXQFFRRZSA-N

一般描述

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.

应用

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.

生化/生理作用

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

包装

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

WGK

WGK 3

闪点(°F)

No data available

闪点(°C)

No data available


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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
Sara L Morales-Lázaro et al.
The Journal of biological chemistry, 289(35), 24079-24090 (2014-07-19)
The transient receptor potential vanilloid 1 (TRPV1) ion channel is a polymodal protein that responds to various stimuli, including capsaicin (the pungent compound found in chili peppers), extracellular acid, and basic intracellular pH, temperatures close to 42 °C, and several
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
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

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