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Synthesis of 1-palmitoyl-2-hexadecyl-sn-glycero-3-phosphocholine (PHPC)

✍ Scribed by Richard I. Duclos Jr.


Book ID
103042296
Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
744 KB
Volume
66
Category
Article
ISSN
0009-3084

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✦ Synopsis


A general method for the chirospecific synthesis of l-acyl-2-alkyl-sn-glycero-3-phosphocholines is described, l-Palmitoyl-2-hexadecyl-sn-glycero-3-phosphocholine (PHPC) was synthesized in 18% overall yield in ten steps via five new synthetic intermediates, and 1-acetyl-2-hexadecyl-sn-glycero-3-phosphocholine (AHPC) was also synthesized. 1-Acyl-2-alkyl-sn-glycero-3-phosphocholines, which have not been found to exist in nature, are ether lipid analogs of 1,2-diacyl-sn-glycero-3-phosphocholines, which are important components of cell membranes. Biophysical studies of hydrated bilayers of PHPC will be of interest in probing the critical importance of the central region of these amphiphilic molecules to the molecular assemblies that are formed.


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