Metabolism and functions of phosphatides: The preparation of a series of <i>L</i>‐α‐lecithins

Das Verfahren zur Synthese von Lecithinen und ihren Ätheranalogen, bei welchem Diacyl‐bzw. Di‐O‐alkyl‐diglyceride (1) mit β‐Bromäthyl‐phosphorsäuredichlorid bei Gegenwart von Triäthylamin umgesetzt werden und anschließend mit Trimethylamin ins Phosphorylcholin 4 übergeführt werden, wurde so abgewandelt, daß beliebige, auch kürzerkettige (bis C8), Lecithine und ihre Ätheranaloga analysenrein und dünnschichtchromatographisch einheitlich erhalten werden (s. Tab. 1).

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Synthesen von Cholinphosphatiden, I. Zur Synthese von α‐ und β‐Lecithinen und ihren Ätheranaloga

Eibl

Arnold

Weltzien

et al. 1967

Justus Liebigs Ann. Chem.

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Synthesis of enantiomeric mixed‐acid phosphatides

Haas

Deenen

1961

Recl. Trav. Chim. Pays‐Bas

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The synthesis is described of two optically pure L-a-lecithins and of one D-a-lecithin, each containing one saturated and one unsaturated fatty acid, and of two enantiomeric a-lecithins composed of two saturated fatty acids of unequal chain length. A modification of the procedure allowed the preparation of two structurally isomeric mixedacid L-a-phosphatidyl-ethanolamines. The suitability of the synthetic phosphatides as substrates for biochemical model studies is demonstrated by experiments with snake-venom phosphatidase.The notable variations within the fatty acid moiety of naturally occurring phosphatides are presumed to be related to the functions of these lipids in biological membranes 2. In addition, a specific location of saturated and unsaturated fatty acids is known to exist on lecithins of various biological origins 3~4 . In order to investigate the possible significance of the asymmetrical distribution of the fatty acids in phosphatides by means of model studies on artificial membrane systems, well-defined mixed-acid phosphatides were required. A preliminary paper dealt with the synthesis of DL-a-lecithins containing two dissimilar saturated fatty acids 5. These compounds proved already to be of interest for the ascertainment of the positional specificity of phosphatidase A 6.Various biochemical problems prompt-

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On the synthesis of isomeric lysophosphatides

Slotboom¹,

Deenen²

1963

Recl. Trav. Chim. Pays‐Bas

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The synthesis is described of two isomeric lysophosphatidylethanolamines, containing the fatty acid residue in the y-and 8-ester position, respectively. The preparation of the (8-stearoyl)-~L-u-lysophosphatidylethanolamine was accomplished by two procedures. According to the first method developed, a silver iodide interchange reaction was carried out between y-0-benzyl-8-stearoylglycerol-a-iodohydrin and silver benzyl 2-phthalimidoethyl phosphate. This procedure was also applied for the synthesis of (y-stearoy1)-DL-a-lysophosphatidylethanolamine by starting from y-stearoyl-8-0-benzylglycerol-u-iodohydrin. A second method involved the preparation of silver benzyl y-0-benzyl-p-stearoylu-glycerol phosphate which was coupled with 2-iodoethylphthalimide. This pathway also furnishes several intermediates which are suitable for the preparation of other types of lysophosphatides. A distinction between both structurally isomeric lysophosphatidyl-ethanolamines by enzymic means proved to be possible. Phospholipase A from snake venom was shown to release the fatty acid constituent from the p-acyl isomer, whereas the y-acyl isomer was not susceptible to the action of this enzyme.Phosphatide mixtures extracted from natural sources have frequently been demonstrated to contain homologues carrying only one fatty acid constituent; such compounds have been denoted as lysophosphatides. Confirming previous observations 2 , the native character of lysolecithins from animal tissues has been recently established 3 . Fresh evidence indicates that naturally occurring lysophosphatides not only result from the catabolism of diacyl-phosphoglycerides, but may play an important part in phosphatide anabolism as well, by acting as substrate for acylating enzymes4.Contribution No 39 in the series: Metabolism and functions of phosphatides. , Rec. trav. chim. 72, 395 (1953). be observed in these experiments between this lecithin and a synthetic one.

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Metabolism and functions of phosphatides: The preparation of a series of L‐α‐lecithins

Abstract: Ten L-a-lecithins have been prepared by acylation of L-a-glycerylphosphorylcholine. Solubilities, RF-values and other physical data are

Cited by 30 publications

References 27 publications

Synthesen von Cholinphosphatiden, I. Zur Synthese von α‐ und β‐Lecithinen und ihren Ätheranaloga

Synthesen von Cholinphosphatiden, I. Zur Synthese von α‐ und β‐Lecithinen und ihren Ätheranaloga

Synthesis of enantiomeric mixed‐acid phosphatides

On the synthesis of isomeric lysophosphatides

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