A method for the synthesis of isomerically pure saturated mixed-chain phosphatidylcholines
β Scribed by Jeffrey T. Mason; Anthony V. Broccoli; Ching-Hsien Huang
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- English
- Weight
- 478 KB
- Volume
- 113
- Category
- Article
- ISSN
- 0003-2697
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β¦ Synopsis
A method is described for the partial synthesis of saturated mixed-chain phosphatidylcholines of a high degree (typically 99 mol%) of purity. This procedure has been designed to eliminate the contamination of the mixed-chain product by symmetric chain phosphatidylcholine and the mixed-chain isomer of the desired product, the two principal impurities introduced by previous techniques. This high degree of purity is obtained by employing a method designed for the complete enzymatic hydrolysis of the C-2 fatty acyl moiety in saturated symmetric phosphatidylcholines and a new technique for the acylation of lysophosphatidylcholines employing the catalyst 4-pyrrolidinopyridine.
The versatility of this new procedure is illustrated with the synthesis of several saturated mixed-chain phosphatidylcholines.
π SIMILAR VOLUMES
A high-yielding procedure for the semisynthesis of mixed-chain phosphatidylethanolamines is described. The key finding is that the reacylation of an N-tBOC-lysophosphatidylethanolamine methyl esterwith a carboxylic acid can be achieved in high yield with DCC and DMAP. Deprotection of the phosphate a
Tertiary phosphine oxides have been prepared with high enantiomeric excesses via intermediate menthyl 2-phosphinylacetates. Optically active phosphine oxides l\_ are key intermediates in the synthesis of bidentate phosphine ligands 2\_ useful for catalytic asymmetric homogeneous hydrogenation. 1) T