52691-62-0Relevant academic research and scientific papers
An effective reagent to functionalize alcohols with phosphocholine
Xu, Lianyan L.,Berg, Lawrence J.,Jamin Keith,Townsend, Steven D.
supporting information, p. 767 - 770 (2020/02/11)
Phosphocholine is a small haptenic molecule that is both a precursor and degradation product of choline. Phosphocholine decorates a number of biologics such as lipids and oligosaccharides. In this study, an air and bench stable phosphocholine donor has been developed and evaluated with a number of alcohol acceptors. Using a one-pot, three-step sequence, (phosphitylation, oxidation, and phosphate deprotection) phosphocholine derivatives are synthesized in high yields. Of particular interest is the synthesis of miltefosine, the lone oral drug approved to treat leishmaniasis. Due to its prohibitive expense ($1500 per g), miltefosine is not accesable for the majority of the world's patients. Based on the described reaction sequence, this drug can be produced for $25 per g.
Synthesis and biophysical characterization of chlorambucil anticancer ether lipid prodrugs
Pedersen, Palle J.,Christensen, Mikkel S.,Ruysschaert, Tristan,Linderoth, Lars,Andresen, Thomas L.,Melander, Fredrik,Mouritsen, Ole G.,Madsen, Robert,Clausen, Mads H.
supporting information; experimental part, p. 3408 - 3415 (2010/03/31)
The synthesis and biophysical characterization of four prodrug ether phospholipid conjugates are described. The lipids are prepared from the anticancer drug chlorambucil and have C16 and C18 ether chains with phosphatidylcholine or phosphatidylglycerol he
Synthesis and biological activity of anticancer ether lipids that are specifically released by phospholipase A2 in tumor tissue
Andresen, Thomas L.,Jensen, Simon S.,Madsen, Robert,J?rgensen, Kent
, p. 7305 - 7314 (2007/10/03)
The clinical use of anticancer lipids is severely limited by their ability to cause lysis of red blood cells prohibiting intravenous injection. Novel delivery systems are therefore required in order to develop anticancer ether lipids (AELs) into clinicall
New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis
Massing, Ulrich,Eibl, Hansjoerg
, p. 211 - 224 (2007/10/02)
A convenient synthesis of new and enantiometrically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described.Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol.These intermediates are converted to 2-O-benzyl- or 2-O-alkyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol.The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition.Also, triglycerides with three different alkyl chains, ester of ether, can be prepared.As an example of the varsatility of the new intermediates, we describe the synthesis of 1-O-hexadecyl-2-O-acetyl-sn-glycero-3-phosphocho;ine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol. Keywords: Synthetic phospholipids; PAF; Phospholipid analogues; Synthesis; Chiral pool; Glyceraldehyde; C-3 building blocks; Optical purity
Isolation and characterization of seven lyso platelet-activating factors and two lyso phosphatidylcholines from the crude drug 'Suitetsu' (the leech, Hirudo nipponica)
Noda,Tanaka,Nishi,Inoue,Miyahara
, p. 1366 - 1368 (2007/10/02)
Nine lyso glycerophospholipids were isolated in the pure state from the crude drug 'Suitetsu', which is the dried body of the leech, Hirudo nipponica (Hirudidae). They were identified as 1-O-hexadecyl-(1), 1-O-octadecyl-(2), 1- O-tetradecyl-(3), 1-O-9-cis-hexadecenyl-(4), 1-O-hexadecanoyl-(5), 1-O- pentadecyl-(6), 1-O-15-methylhexadecyl-(7), 1-O-octadecanoyl-(8) and 1-O- heptadecyl-sn-glycero-3-phosphocholine (9). Two of them (5 and 8) are lysophosphatidylcholines and the other seven are lyso platelet-activating factors. One of them has an alkenyl carbon chain.
Formation of a Structural Isomer of Platelet Activating Factor on the Acetylation of 1-Alkyl-sn-Glycero-3-Phosphocholines
Chupin, V. V.,Ostanenko, O. V.,Klykov, V. N.,Anikin, M. V.,Serebrennikova, G. A.
, p. 667 - 674 (2007/10/02)
The key stage in the synthesis of the platelet activating factor (PAT) - the acetylation of 1-alkyl-sn-glycero-3-phosphocholines (lyso-PAT) with acetic anhydride - has been studied.The formation of a structural isomer of PAT - 1-alkyl-3-acetyl-sn-glycero-3-phosphocholines - as a by-product when the reaction is carried out in the presence of bases (triethylamine, 4-dimethylaminopyridine) has been shown.Acetylation under the conditions of acid catalysis gave the isomerically pure PAT.The mechanism of the reaction leading to the formation of the PAT isomer is discussed.
Syntheses of a glycerophospholipid, C16-platelet activating factor and a palmitoyl analogue of M-5, an anti-inflammatory glyceroglycolipid
Shibuya,Kawashima,Narita,Kitagawa
, p. 1166 - 1169 (2007/10/02)
From a chiral C4-epoxide (-)-3, which is one of the synthons in our synthetic strategy for complex lipids, a glycerophospholipid C16-platelet activating factor (C16-PAF, 1) and a palmitoyl analogue (2) of an anti-inflammatory glyceroglycolipid M-5, which was previously isolated from the Okinawan marine sponge Phyllospongia foliascens, have been synthesized.
An efficient synthesis of Platelet-Activating Factor (PAF) via 1-o-alkyl-2-o-(3-isoxazolyl)-SN-glycero-3-phosphocholine, a new PAF agonist utilization of the 3-isoxazolyloxy group as a protected hydroxyl
Nakamura, Norio,Miyazaki, Hideki,Ohkawa, Nobuyuki,Oshima, Takeshi,Koike, Hiroyuki
, p. 699 - 702 (2007/10/02)
Potent PAF agonists (R)-3a,b were synthesized and converted into PAF. Key steps include Mitsunobu reaction of a chiral secondary alcohol with 3-hydroxyisoxazole as the acidic component, and hydrogenolytic ring cleavage of the resulting 3-isoxazolyloxy gro
An Efficient Stereocontrolled Route to Both Enantiomers of Platelet Activating Factor and Analogues with Long-Chain Esters at C2: Saturated and Unsaturated Ether Glycerolipids by Opening of Glycidyl Arenesulfonates
Guivisdalsky, Pedro N.,Bittman, Robert
, p. 4643 - 4648 (2007/10/02)
Both enantiomers of various ether/ester glycerophospholines (R)- and (S)-1, including platelet activating factor (PAF, 2), have been synthesized from arenesulfonate derivatives of glycidol ((R)- and (S)-3) that are readily available in high enantiomeric p
