Synthesis of Unsaturated α-Lecithins.<sup>1</sup> I. L-α-(Dioleyl)-lecithin

Baer, Erich; Buchnea, Dmytro; Newcombe, Alan G.

doi:10.1021/ja01582a064

Cited by 67 publications

(8 citation statements)

References 2 publications

(2 reference statements)

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“…The structure of Ix was further proven by subjecting this compound to an acylation with [9,10-aH]-stearoyl chloride (scheme 2). The reaction product 3-[9,10-3H]-stearoyl-2-stearoyl-glycerol -lphosphorylcholine (XII) was found to have an optical rotation, [~]~°--5.9°, being in fair agreement with values reported for lecithins derived of glycerol-1-phosphate [13][14][15]. This compound (xI0 was dephosphorylated using a mixture of acetic acid and acetic anhydride 16) so as to give 3-[9,10-aH]-stearoyl -2-stearoyl-l-acetyl glycerol (Mll).…”

Section: Lysolecithinsupporting

confidence: 79%

Synthesis of lysophosphoglycerides

Slotboom

Deenen

1967

Chemistry and Physics of Lipids

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Section: Lysolecithinsupporting

confidence: 79%

Synthesis of lysophosphoglycerides

Slotboom

Deenen

1967

Chemistry and Physics of Lipids

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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.…”

mentioning

confidence: 89%

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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“…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. In this method ( Fig.…”

Section: Phosphatidyi-cholines Ipcimentioning

confidence: 99%

“…Baer et al (45), drawing upon their experience with PCs, prepared PE in much the same fashion. The amino function in ethanolamine phosphatidyl choline (36).…”

Section: Phosphati Dyl Ethanolami N Es (Pe)mentioning

confidence: 99%