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Synthesis of Stereoisomeric Phospholipids for Use in Membrane Studies

  • M. Kates

Abstract

Twenty-five years ago, the first successful synthesis of a 3-sn-phosphatidylcholine was reported by Baer and Kates (1950). This accomplishment not only established conclusively the constitution and configuration of a naturally occurring phospholipid as being “L-α-,” or, in the newer nomenclature, “3-sn-,” but made a phospholipid available for the first time in pure form for biochemical and biophysical studies. The procedure used involved phosphorylation of a 1,2-diacyl-sn-glycerol with monophenylphosphoryl dichloride, followed by esterification with choline chloride and removal of the phenyl group by catalytic hydrogenolysis (Fig. 1). Variations of this procedure have since been used by Baer and his coworkers to synthesize all the major classes of phosphoglycerides (e.g., phosphatidylethanolamines, phosphatidylserines, phosphatidylglycerols, etc.), as well as minor and unusual phosphoglycerides, including ether and/or phosphono analogues (see reviews by Baer, 1963, 1965).

Keywords

Phosphatidic Acid Blocking Group Silver Salt Phosphorus Oxychloride Glycerol Ether 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Press, New York 1977

Authors and Affiliations

  • M. Kates
    • 1
  1. 1.Department of BiochemistryUniversity of OttawaOttawaCanada

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