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857119P

Avanti

06:0 Lyso PA

1-hexanoyl-2-hydroxy-sn-glycero-3-phosphate (ammonium salt), powder

Synonym(s):
1-hexanoyl-sn-glycero-3-phosphate (ammonium salt); PA(6:0/0:0)
Empirical Formula (Hill Notation):
C9H22NO7P
CAS Number:
Molecular Weight:
287.25
NACRES:
NA.25

assay

>99% (LPA; may contain up to 10% of the 2-LPA isomer, TLC)

form

powder

packaging

pkg of 1 × 25 mg (857119P-25mg)

manufacturer/tradename

Avanti Polar Lipids 857119P

shipped in

dry ice

storage temp.

−20°C

SMILES string

O[C@](COP([O-])(O)=O)([H])COC(CCCCC)=O.[NH4+]

General description

Lysophosphatidic acid (LPA) belongs to a class of phospholipids, that has a glycerol backbone attached by a phosphate group, an aliphatic chain and a hydroxyl group. It has a phosphate group attached to sn-3 position, an aliphatic chain attached to sn-1 or sn-2 position and the hydroxyl group attached to the remaining sn-1 or sn-2 position. 06:0 Lyso PA/HHGP, belongs to the LPA (lysophosphatidic acid) family. It is a negatively charged single chain lipid.
Lysophosphatidic acid (LPA) has a free hydroxyl and phosphate moiety. It is hydrophilic and is not associated with the membrane. It is the major constituent of serum.

Application

06:0 Lyso PA (LPA) has been used in the structure-activity relationship (SAR) analysis with G-protein receptor GPR92. It has also been used in lipid assay in the treatment of serum-starved primary mouse embryonic fibroblast cells.
06:0 Lyso PA has been used to study the role of lipid binding to MxiM protein in co‐crystallization experiments.

Biochem/physiol Actions

Lysophosphatidic acid (LPA) participates in several biological functions. LPA stimulates platelet aggregation, chemotaxis, cytoskeleton rearrangement, Ca2+ mobilization and cell proliferation. 06:0 Lyso PA/HHGP possesses a micromolar binding affinity for global regulator of LEE (locus of enterocyte effacement) repressor (GrlR) and for β-lactoglobulin.
Lysophosphatidic acid (LPA) is the precursor for the synthesis of phospholipids in eukaryotes and prokaryotes. It acts as an intercellular signaling molecule. Activated platelets produce LPA. It plays a major role in tissue healing and wound regeneration. LPA binds to G-protein coupled receptors. It possesses mitogenic properties. LPA inhibits differentiation of neuroblastoma and myoblast, aids in neurotransmitter release and smooth muscle contraction. It is a potential biomarker for ovarian and gynecological cancers. It is implicated in the initiation of neuropathic pain.

Packaging

5 mL Amber Glass Screw Cap Vial (857119P-25mg)

Storage Class Code

13 - Non Combustible Solids

Certificate of Analysis

Certificate of Origin

Structure and biochemical analysis of a secretin pilot protein
Lario PI, et al.
The Embo Journal, 24(6), 1111-1121 (2005)
Lysophosphatidic acid as a potential biomarker for ovarian and other gynecologic cancers
Xu Y, et al.
JAMA : The Journal of the American Medical Association, 280(8), 719-723 (1998)
Identification and characterization of the lipid-binding property of GrlR, a locus of enterocyte effacement regulator
Jobichen C, et al.
The Biochemical Journal, 420(2), 191-201 (2009)
Unique ligand selectivity of the GPR92/LPA5 lysophosphatidate receptor indicates role in human platelet activation
Williams JR, et al.
The Journal of Biological Chemistry, 284(25), 17304-17319 (2009)
Diacylglycerol kinase zeta regulates actin cytoskeleton reorganization through dissociation of Rac1 from RhoGDI
Abramovici H, et al.
Molecular Biology of the Cell, 20(7), 2049-2059 (2009)

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