26662-95-3

Usage

Uses

Used in Pharmaceutical Industry:
1-Palmitoyl-2-linoleoyl PE is used as a component in lipid-based formulations for the delivery of therapeutic agents, particularly mRNA, into cells. This application is crucial for the development of treatments for various diseases, including cancer and viral infections.
In the context of mRNA delivery, sn-PLPE is used as a carrier lipid to facilitate the efficient and targeted delivery of mRNA into cells. This is essential for the successful translation of the therapeutic mRNA into functional proteins, which can then exert their therapeutic effects.
Overall, 1-Palmitoyl-2-linoleoyl PE plays a vital role in the development of advanced drug delivery systems, particularly for the delivery of mRNA-based therapeutics, offering promising potential for the treatment of a wide range of diseases.

Upstream product

• 141-43-5 ethanolamine 
• 17708-90-6 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine 
• 63-89-8 L-α-Dipalmitoylphosphatidylcholine 
• 131099-10-0 O-<2-(N-(tert-butyloxycarbonyl)amino)ethyl> O-methyl O-(1'-O-palmitoyl-sn-3'-glyceryl) phosphate 
• 160531-65-7 2-O-(benzyloxymethyl)-1-O-palmitoyl-sn-glycerol 
• 139100-83-7 3-O-(p-methoxybenzyl)-1-O-palmitoyl-sn-glycerol 
• 60-33-3 linoleic acid 
• 160531-67-9 O-<2-(N-(tert-butyloxycarbonyl)amino)ethyl> O-(2'-O-linoleoyl-1'-O-palmitoyl-sn-3'-glyceryl) O-methyl phosphate 
• 160531-66-8 O-<2-(N-(tert-butyloxycarbonyl)amino)ethyl> O-methyl O-(1'-O-palmitoyl-2'-O-(benzyloxymethyl)-sn-3'-glyceryl) phosphate 
• 161270-99-1 2-O-(benzyloxymethyl)-3-O-(p-methoxybenzyl)-1-O-palmitoyl-sn-glycerol 

Downstream Products

• 13190-01-7 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine 

Relevant academic research and scientific papers

General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-glycerols

An efficient phosphite coupling protocol is described for the syntheses of the major classes of phospholipids that are derived from 1,2-O-diacyl-sn-glycerols and analogues thereof.The symmetrical diacyl glycerols 10c,d were prepared by straightforward acylation of 3-O-benzyl-sn-glycerol (7) with the appropriate carboxylic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP).A simple method for preparing saturated and unstaturated mixed 1,2-O-diacyl-sn-glycerols was then devised that involved stepwise acylation of 7 with different alkyl carboxylic acids and debenzylation; this procedure is exemplified by the preparation of 10a,b.The 1,2-O-diacyl-sn-glycerols 10a-d were then coupled with suitably protected lipid head groups employing reactive alkyl or aryl dichlorophosphites to give intermediate phosphite triesters in high overall yields.Oxidation or sulfurization of these phosphites proceeded smoothly to give the corresponding phosphate or phosphorothioate triesters, deprotection of which then provided the phosphatidylcholines 16 and 17, the phosphatidylethanolamine 20, the phosphatidylserine 28, and the phosphatidylinositols 37 and 38.Preparation of 37 and 38 required the invention of an improved method for resolving the isopropylidene-protected D-myo-inositol derivative 33.This phosphite coupling procedure was modified to assemble phospholipids bearing polyunsaturated acyl side chains at the sn-2-position as exemplified by the preparation of the phosphatidylethanolamine 26.The one-pot phosphite coupling procedure is also applicable to the syntheses of a variety of other biologically interesting phospholipid analogues.For example, the phosphatidylinositol analogues 49-51, in which the hydroxyl group at C(2) of the inositol ring has been modified, were prepared in excellent overall yields by conjoining the 1,2-O-diacyl-sn-glycerol 10c with the protected inositol derivatives 44, 45, and 48.Phospholipid analogues that contain other replacements of the phosphate group including phosphoramidates and thiophosphates may be prepared as evidenced by the syntheses of 56 and 61 in which the sn-3 oxygen atom of the 1,2-O-diacyl-sn-glycerol moiety is replaced with an N-benzyl group or a sulfur atom, respectively.

MASS SPECTROMETRY OF PHOSPHOLIPIDS. SOME APPLICATIONS OF DESORPTION CHEMICAL IONIZATION AND FAST ATOM BOMBARDMENT

Major diagnostic peaks in desorption chemical ionization (D/CI) and fast atom bombardment (FAB) mass spectra of various model synthetic phospholipids and related compounds are reported in conjunction with our ongoing research on marine phospholipids.Similarities and differences with some previous studies are presented.Commercially available or partially synthesized, saturated or unsaturated fatty acid containing phospholipids with different head groups such as choline, ethanolamine, mono- and dimethylethanolamine, serine, and glycerol were investigated.For identification purposes, 1,2-diacetylglycerol, 1,2-diacetyl-sn-glycero-3-phosphocholine, and 1,2-dipalmitoyl-sn-glycero-3-phosphocholine-d9 were also prepared and their mass spectral behavior studied.In terms of diagnostically useful fragmentations ammonia proved to be superior to methane as reagent gas for chemical ionization.The use of deuterated ammonia shed light on the nature of several fragmentations.In most cases, both chemical ionization and fast atom bombardment techniques exhibited molecular ions and/or related peaks.Desorption chemical ionization with ammonia provided more information about fatty acyl moieties, while fast atom bombardment gave diagnostic peaks about various head groups.These two techniques thus offer comlementary information about the structures of intact phospholipids.