22252-07-9

Basic information

• Product Name: 1-LINOLEOYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHORYLCHOLINE
• Synonyms: 1-LINOLEOYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHORYLCHOLINE
• CAS NO: 22252-07-9
• Molecular Weight: 519.659
• Mol File: 22252-07-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-LINOLEOYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHORYLCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-LINOLEOYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHORYLCHOLINE(22252-07-9)
• EPA Substance Registry System: 1-LINOLEOYL-2-HYDROXY-SN-GLYCERO-3-PHOSPHORYLCHOLINE(22252-07-9)

Safety Data

• Hazardous Substances Data: 22252-07-9(Hazardous Substances Data)

Usage

General Description

1-Linoleoyl-2-Hydroxy-sn-Glycero-3-Phosphorylcholine, also known as LysoPC(18:2(9Z,12Z))/LysoPtdCho(18:2(9Z,12Z)), is a chemical compound that belongs to the class of chemical entities known as lysophosphatidylcholines. It is a lipid molecule primarily composed of a phosphocholine head group and a linoleic acid attached to the glycerol backbone. This chemical finds use in scientific research, particularly in the area of lipidomics, as it is crucial for understanding cellular functions. Lysophosphatidylcholines like 1-Linoleoyl-2-Hydroxy-sn-Glycero-3-Phosphorylcholine are known to play a role in various biological processes, including signal transduction, apoptosis, and immune response.

Upstream product

• 998-06-1 (R)-2,3-bis(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)propyl (2-(trimethylammonio)ethyl) phosphate 

Relevant articles and documents

Mechanism for remodeling of the acyl chain composition of cardiolipin catalyzed by Saccharomyces cerevisiae tafazzin

Remodeling of the acyl chains of cardiolipin (CL) is responsible for final molecular composition of mature CL after de novo CL synthesis in mitochondria. Yeast Saccharomyces cerevisiae undergoes tafazzin-mediated CL remodeling, in which tafazzin serves as a transacylase from phospholipids to monolyso-CL (MLCL). In light of the diversity of the acyl compositions of mature CL between different organisms, the mechanism underlying tafazzin-mediated transacylation remains to be elucidated. We investigated the mechanism responsible for transacylation using purified S. cerevisiae tafazzin with liposomes composed of various sets of acyl donors and acceptors. The results revealed that tafazzin efficiently catalyzes transacylation in liposomal membranes with highly ordered lipid bilayer structure. Tafazzin elicited unique acyl chain specificity against phosphatidylcholine (PC) as follows: linoleoyl (18:2) > oleoyl (18:1) = palmitoleoyl (16:1) ? palmitoyl (16:0). In these reactions, tafazzin selectively removed the sn-2 acyl chain of PC and transferred it into the sn-1 and sn-2 positions of MLCL isomers at equivalent rates. We demonstrated for the first time that MLCL and dilyso-CL have inherent abilities to function as an acyl donor to monolyso-PC and acyl acceptor from PC, respectively. Furthermore, a Barth syndrome-associated tafazzin mutant (H77Q) was shown to completely lack the catalytic activity in our assay. It is difficult to reconcile the present results with the so-called thermodynamic remodeling hypothesis, which premises that tafazzin reacylates MLCL by unsaturated acyl chains only in disordered non-bilayer lipid domain. The acyl specificity of tafazzin may be one of the factors that determine the acyl composition of mature CL in S. cerevisiae mitochondria.

Short-route Synthesis of a Glycerophospholipid Bearing an Unsaturated Acyl Group at the sn-1 Position

A short-route synthesis of an optically active phosphocholine bearing an unsaturated acyl group at the sn-1 position was developed via lipase-catalyzed enantioselective acylation of 2-O-methoxyethoxymethylglycerol, removal of the MEM group by employing catechol boron bromide, subsequent DCC-mediated acylation of the hydroxy group at the 2-position and final introduction of a choline phosphate moiety.