857119P
Avanti
06:0 Lyso PA
Avanti Research™ - A Croda Brand
Synonym(s):
1-hexanoyl-sn-glycero-3-phosphate (ammonium salt); PA(6:0/0:0)
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About This Item
Empirical Formula (Hill Notation):
C9H22NO7P
CAS Number:
Molecular Weight:
287.25
UNSPSC Code:
51191904
NACRES:
NA.25
description
1-hexanoyl-2-hydroxy-sn-glycero-3-phosphate (ammonium salt)
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 Research™ - A Croda Brand
lipid type
cardiolipins
phospholipids
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) 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.
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.
Packaging
5 mL Amber Glass Screw Cap Vial (857119P-25mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class Code
11 - Combustible Solids
Certificates of Analysis (COA)
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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)
Lysophosphatidic acid: G-protein signalling and cellular responses
Moolenaar WH, et al.
Current Opinion in Cell Biology, 9(2), 168-173 (1997)
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