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Citation: Huang Yan, Madeleine Picq, Georges Némoz, Alain Doutheau, Michel Lagarde. Synthesis of Phosphatidylcholine Analogues Bearing Aromatic Group[J]. Chinese Journal of Applied Chemistry, ;1999, 16(5): 88-90. shu

Synthesis of Phosphatidylcholine Analogues Bearing Aromatic Group

1.
a Guangzhou Medical College, Guangzhou 510182;
2.
b Institut National des Sciences Appliquées de Lyon, 69621 Villeurbanne, France

Received Date: 13 January 1999
Available Online: 7 May 1999

The acylation reactions of L-α-Lysophosphatidylcholine(Lyso PC) or L-α-Glycerophosphorylcholine.CdCl₂(GPC-CdCl₂) with fatty acid bearing bulky aromatic group or corresponding anhydride have been investigated. The acylation of Lyso PC with fatty acid bearing bulky aromatic group in the presence of condensing reagent N,N'-dicyclohexylcarbodiimide(DCC) and catalyst 4-(N,N'-dimethylamino) pyridine(DMAP) was found to be more convenient and more efficient than that of Lyso PC with the corresponding fatty acid anhydride prepared prior to acylation(yield 85% to 45%). The poor formation of anhydride from fatty acid is responsible largely for the low yield. It was found that the acylation reaction of Lyso PC or GPC CdCl 2 with fatty acid bearing bulky aromatic group could be accomplished in 85% and 74% yield respectively by using a fatty acid/Lyso PC(or GPC CdCl₂) molar ratio of 4, DMAP/Lyso PC(or GPC CdCl₂) molar ratio of 4 and DCC/fatty acid molar ratio of 0.6 (1 for the acylation of GPC CdCl₂). The procedures described provide significant improvements in yield over methods repor ted
- phosphatidylcholine,
- phosphatide analogues,
- synthesis,
- acylation
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