74389-68-7Relevant articles and documents
On the synthesis of platelet-activating factor via acetylation of 1-alkyl-sn-glycero-3-phosphocholine. Formation of structural isomer of PAF in the presence of bases
Chupin,Ostapenko,Klykov,Anikin,Screbrennikova
, p. 35 - 43 (1996)
It has been shown that platelet-activating factor (PAF) specimens prepared via acetylation of 1-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) with acetic anhydride are heterogeneous. The contaminated compound was isolated and identified to be the structural isomer of PAF, 1-alkyl-3-acetyl-sn-glycero-2-phosphocholine (iso-PAF). It appeared, that iso-PAF is formed when performing the reaction in the presence of organic bases, but not under acid catalysis. The mechanism of iso-PAF formation is discussed.
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
Novel chemo-enzymatic synthesis of optically active platelet activating factor
Kumar,Bhakuni
, p. 3463 - 3466 (2007/10/02)
This paper describes an enantioselective enzymatic synthesis of biologically active platelet activating factor (PAF) starting from chloropyruvic acid.
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.
A Convenient Synthesis of Platelet-Activating Factors and Their Analogues from Chiral Epichlorohydrin
Tsuboi, Sadao,Takeda, Shinji,Yamasaki, Yasuhisa,Sakai, Takashi,Utaka, Masanori,et al.
, p. 1417 - 1420 (2007/10/02)
Two platelet activating factors (PAF) were conveniently prepared from optically active epichlorohydrin via 5 steps in 15-16percent total yield.Four analogues containing oleoyl, propyl, p-trifluoromethylphenoxy, and N,N-dimethyldithiocarbamoyl groups were also prepared.
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.
Synthesis of 1-O-alkyl-2-O-acetyl-Sn-3-glyceryl-3-phosphoryl choline the enantiomer of platelet activating factor (PAF)
Kumar,Shanker
, p. 1763 - 1768 (2007/10/02)
A novel sterospecific synthesis of biologically active ether-phospholipids (PAF) is reported, involving chemoenzymatic approach.
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
