An Improved Procedure for the Synthesis of Enantiomeric α-Lecithins

Baer, Erich; Maurukas, Jonas

doi:10.1021/ja01121a039

Cited by 43 publications

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“…In the experimental part of this paper we describe the synthesis of the distearoyl-, dimyristoyl-, and dioleoyl-L-a-lecithins. These are identical in every respect with the corresponding lecithins prepared by our other methods (2,3,4,12). The synthesis of lecithins from L-a-GPC containing either shorter c r more highly unsaturated fatty acid substituents is in progress in this laboratory.…”

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“…The L-a-lecithins are obtained in fairly good yields, and are both optically and chromatographically pure. However, since the preparation of I~-~-G P C by the method of Baer and Kates (1) was rather time consuming, and in the meantime other satisfactory methods for the synthesis of saturated (2,4) and unsaturated L-a-lecithins (3) had been developed in this laboratory no detailed report of the synthesis of lecithins by acylation of the cadnlium chloride compound of L-a-GPC was made. I t was mentioned, however, in a discussion following a lecture given by one of the authors a t a Symposium on the Chemistry and Physiology of Phospholipids a t the University of Western Ontario (5).…”

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

Baer

Buchnea

1959

Can. J. Biochem. Physiol.

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

Baer

Buchnea

1959

Can. J. Biochem. Physiol.

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113

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“…Phosphatidyl choline was obtained by purification through the reineckate, and the protective phenyl group removed by hydrogenolysis. In a later paper (35) an improved procedure for purification involving washing with various solvents was presented, but hydrogenolysis was still required. Continuing their syntheses of phosphatidyl cholines, Baer et al (36) prepared the dioleoyl compound.…”

Section: Phosphatidyi-cholines Ipcimentioning

confidence: 99%

Synthesis of phosphoglycerides

Jensen

Gordon

1972

Lipids

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“…They showed that hydrogenation of this material produced the corresponding saturated lecithin which was identical with the synthetic L-oc-(dipalmitoyl)-lecithin of Baer and Maurukas (1952). The latter compound, when used in combination with cardiolipin and cholesterol, has given antigens suitable for the sero-diagnosis of syphilis (Tonks and Allen, 1953).…”

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