Synthesis of mixed-acid phosphatidylserine containing unsaturated fatty acids

The synthesis is described of a mixed-acid phosphatidylserine, containing one saturated and one unsaturated fatty acid, by a reaction between γ,β-diacylglycerol-L-α-iodohydrin and silver N-t. butoxycarbonyl-O-(O-benzylphospho)-DL-serine t. butyl ester. Some physical and biochemical properties of the unsaturated phosphatidylserine, viz. (γ-oleoyl-β-palmitoyl)-L-α-phosphatidyl-DL-serine, are given.

[1]  L. M. Deenen,et al.  Synthesis of enantiomeric mixed‐acid phosphatides , 2010 .

[2]  L. M. Deenen,et al.  Synthesis of N-phthaloyl-L-serine-t. butyl ester , 2010 .

[3]  F. Daemen,et al.  An improved synthesis of a mixed acid l‐α‐phosphatidylethanolamine, containing a polyunsaturated fatty acid , 2010 .

[4]  G. de Haas,et al.  Hydrolysis of synthetic mixed-acid phosphatides by phospholipase A from human pancreas. , 1963, Biochimica et biophysica acta.

[5]  G. de Haas,et al.  The site of action of phosphatide acyl-hydrolase (phospholipase A) on mixed-acid phosphatides containing a poly-unsaturated fatty acid. , 1962, Biochimica et biophysica acta.

[6]  P. E. Peterson,et al.  Solvents of Low Nucleophilicity. II. Addition of Trifluoroacetic Acid to Alkenes and Cycloalkenes1 , 1962 .

[7]  F. Weygand,et al.  Acylierung von Aminosäuren mitpHT‐Methoxybenzyloxycarbonyl‐azid , 1962 .

[8]  J. Gier,et al.  Some lipid characteristics of red cell membranes of various animal species , 1961 .

[9]  F. Cramer,et al.  Imidoester, VII. Trichloracetonitril, ein Reagenz zur selektiven Veresterung von Phosphorsäuren , 1961 .

[10]  L. M. Deenen,et al.  The mode of action of phospholipase A on synthetic “mixed-acid” L-α-phosphatidyl ethanolamines , 1961 .

[11]  R. Thompson,et al.  The estimation of phospholipase A activity in aqueous systems. , 1960, The Biochemical journal.

[12]  R. Dawson,et al.  The phospholipids of the erythrocyte 'ghosts' of various species. , 1960, The Biochemical journal.

[13]  K. Fontell,et al.  Alteration of some long-chain esters during gas-liquid chromatography. , 1960, Journal of lipid research.

[14]  Y. Kimura,et al.  Infrared spectra of brain phosph-atidlserine. , 1960, The Biochemical journal.

[15]  G. de Haas,et al.  On the specificity of phospholipase A. , 1960, Biochemical and biophysical research communications.

[16]  G. W. Anderson,et al.  t-Butyl Esters of Amino Acids and Peptides and their Use in Peptide Synthesis1 , 1960 .

[17]  L. A. Carpino,et al.  O-Acylhydroxylamines. I. Synthesis of O-Benzoylhydroxylamine1 , 1959 .

[18]  R. Schwyzer,et al.  Zur Synthese von N‐t‐Butyloxycarbonyl‐aminosäuren , 1959 .

[19]  S. Hünig,et al.  Synthesen mit Enaminen, I. Acylierung mit Carbonsäurechloriden , 1957 .

[20]  M. Karnovsky,et al.  The titration of some phosphatides and related compounds in a non-aqueous medium. , 1956, The Journal of biological chemistry.

[21]  OkawaKenzi.  Studies on Serine Peptides. I. Optical Resolution of O -Benzyl- DL -serine and Synthesis of DL -Serine Peptides , 1956 .

[22]  E. Nicolaides,et al.  Azaserine, Synthetic Studies. II , 1954 .

[23]  J. Baddiley,et al.  176. Studies on phosphorylation. Part V. The reaction of tertiary bases with esters of phosphorous, phosphoric, and pyrophosphoric acids. A new method of selective debenzylation , 1949 .

[24]  Hilton A. Smith,et al.  Heats of Organic Reactions. II. Hydrogenation of Some Simpler Olefinic Hydrocarbons , 1935 .