Glycerophospholipid Synthesis: Improved General Method and New Analogs Containing Photoactivable Groups

Overview

Journal Proc Natl Acad Sci U S A

Specialty Science

Date 1977 Oct 1

PMID 270675

Citations 56

Authors

C M Gupta

R Radhakrishnan

H G Khorana

Affiliations

Soon will be listed here.

Abstract

Current methods for phospholipid synthesis involving acylation of sn-glycero-3-phosphorylcholine, lysolecithins, and related glycerophosphate esters are not satisfactory. With N,N-dimethyl-4-aminopyridine as a catalyst and moderate amounts of fatty acid anhydrides (1.2-1.5 mol equiv per OH group), diacyl or 1,2-mixed diacylphosphatidylcholines, N-protected phosphatidylethanolamines, and phosphatide acids now can be conveniently prepared in high yields (75-90%). New phospholipids containing photoactivable groups, such as trifluorodiazopropionyl, diazirinophenoxy, 2-nitro-4-azidophenoxy, m-azidophenoxy, and alpha, beta-unsaturated keto groups, in the fatty acyl chains have been prepared. These phospholipids are of interest in studies of lipid-lipid and lipid-protein interactions in biological membranes.

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