Selective Reduction of Phospholipids with Lithium Aluminum Hydride I. Ovolecithin

Urakami, Chieko; Okura, Hirochika; Okada, Mitsuko

doi:10.1246/bcsj.31.779

Cited by 9 publications

(3 citation statements)

References 8 publications

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“…product as described above (see experiment I ) , gave 2.2 g (44% of theory) of L-a-(distearoy1)lecithin. [ a ] , +5.2" in chloroform-methanol (1 : 1, v/v), c 10 …”

Section: Methodsmentioning

confidence: 99%

SYNTHESIS OF SATURATED AND UNSATURATEDL-α-LECITHINS ACYLATION OF THE CADMIUM CHLORIDE COMPOUND OFL-α-GLYCERYLPHOSPHORYLCHOLINE

Baer

Buchnea

1959

Can. J. Biochem. Physiol.

113

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A facile procedure for the preparation of saturated and ulisaturated L-a-lecithins from L-a-glycerylphosphorylcholine (GPC) is reported. The lecithins are obtained by acylating I.-a-GPC, in the form of its cadmium chloride addition compound, with fatty acjd chloride and pyritline a t low temperature (0°-2.5'). The acylation proceeds rap~dly and yields optically pure L-a-lecithins. The preparation of the tlistex-oyl-, dimyristoyl-, and dioleoyl L-a-lecithi 11s by this procedure is described.The deacylatioil of lecithins with mercuric chloride or sodium hydroxide was investigated. Both procedures give a partially racemized L-a-GPC. This was established by the finding that the optical activity of the lecithins resulting from reacylating the L-a-GPC preparations in the form of their cadmium chloride compountls was considerably lower than that of the corresponding authentic lecithins.Can. J. Biochem. Physiol. Downloaded from www.nrcresearchpress.com by University of Otago on 07/29/15For personal use only.

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“…product as described above (see experiment I ) , gave 2.2 g (44% of theory) of L-a-(distearoy1)lecithin. [ a ] , +5.2" in chloroform-methanol (1 : 1, v/v), c 10 …”

Section: Methodsmentioning

confidence: 99%

SYNTHESIS OF SATURATED AND UNSATURATEDL-α-LECITHINS ACYLATION OF THE CADMIUM CHLORIDE COMPOUND OFL-α-GLYCERYLPHOSPHORYLCHOLINE

Baer

Buchnea

1959

Can. J. Biochem. Physiol.

113

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“…GPC can be obtained by deacylation of lecithin with mercuric chloride, [75] methanolic NaOH, [76] lithium aluminium hydride, [77] alkaline hydroxylamine, [78] or methanolic tetrabutylammonium hydroxide solution, [79,80] in 60–85 % yields.…”

Section: Sn‐glycero‐3‐phosphocholine (Gpc)mentioning

confidence: 99%

“…[27] Recently, the use of racemic or optically pure (S) or (R)-3halo-1,2-propanediol instead of glycidol has been patented in the reaction with choline phosphate to prepare racemic or optically active GPC in high yield (97 %) and gram scale. [74] GPC can be obtained by deacylation of lecithin with mercuric chloride, [75] methanolic NaOH, [76] lithium aluminium hydride, [77] alkaline hydroxylamine, [78] or methanolic tetrabutylammonium hydroxide solution, [79,80] in 60-85 % yields.…”

Section: Chemical Approachesmentioning

confidence: 99%

Chemical and Enzymatic Approaches to Esters ofsn‐Glycero‐3‐Phosphoric Acid

et al. 2021

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Esters of sn‐glycero‐3‐phosphoric acid (GPAE) are derivatives of glycerophospholipids in which both the fatty acid chains in sn‐1 and sn‐2 positions are removed. Phosphatidylcholine (PC), phosphatidylethanolamine (PE), phosphatidylinositol (PI), and phosphatidylserine (PS) are the most abundant glycerophospholipids in Nature. Their deacylated derivatives find application in many industrial sectors; for example, sn‐glycero‐3‐phosphocholine (GPC) is useful as a cognitive enhancer and as a food ingredient, whereas sn‐glycero‐3‐phosphoinositol (GPI) acts as a natural anti‐inflammatory agent. This minireview covers the state‐of‐the‐art of chemical and biocatalytic methods for the obtainment of these lipid‐derived components.

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

Kögl

Haas

Deenen

1960

Recl. Trav. Chim. Pays‐Bas

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Selective Reduction of Phospholipids with Lithium Aluminum Hydride I. Ovolecithin

Cited by 9 publications

References 8 publications

SYNTHESIS OF SATURATED AND UNSATURATEDL-α-LECITHINS ACYLATION OF THE CADMIUM CHLORIDE COMPOUND OFL-α-GLYCERYLPHOSPHORYLCHOLINE

SYNTHESIS OF SATURATED AND UNSATURATEDL-α-LECITHINS ACYLATION OF THE CADMIUM CHLORIDE COMPOUND OFL-α-GLYCERYLPHOSPHORYLCHOLINE

Chemical and Enzymatic Approaches to Esters ofsn‐Glycero‐3‐Phosphoric Acid

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

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