PHOSPHONOLIPIDS: XII. Synthesis of Phosphonolipid Metobolites. L-α-Glyceryl-(2-aminoethyl) phosphonate

1967 ◽  
Vol 45 (11) ◽  
pp. 1755-1761 ◽  
Author(s):  
Erich Baer ◽  
G. Raghupati Sarma
Keyword(s):  
Phosphonic Acid ◽  
Condensation Product ◽  
Acid Analogue

The synthesis of L-α-glyceryl-(2-phthalimidoethyl)phosphonic acid and of L-α-glyceryl-(2-aminoethyl)phosphonate, the latter a phosphonic acid analogue of L-α-glycerylphosphorylethanolamine and a possible intermediate in phosphonolipid metabolism, is described. The compounds were obtained by condensing D-acetone glycerol with (2-phthalimidoethyl)metaphosphonate in boiling benzene, and freeing the condensation product, viz. acetone L-α-glyceryl-(2-phthalimidoethyl)phosphonic acid, of its acetone group to obtain L-α-glyceryl-(2-phthalimidoethyl)phosphonic acid, or of its phthaloyl and acetone groups to give L-α-glyceryl-(2-aminoethyl)phosphonate.A procedure for the preparation of (2-phthalimidoethyl)metaphosphonate is reported.

PHOSPHONOLIPIDS: XI. SYNTHESIS OF PHOSPHONOLIPID METABOLITES. L-α-GLYCERYL-(2-TRIMETHYLAMMONIUMETHYL)PHOSPHONATE

1967 ◽  
Vol 45 (11) ◽  
pp. 1747-1754 ◽  
Author(s):  
Erich Baer ◽  
Ranga Robinson
Keyword(s):  
Acid Hydrolysis ◽  
Phosphonic Acid ◽  
Cadmium Chloride ◽  
Condensation Product ◽  
Hydrolysis Product ◽  
Chloride Complex ◽  
Acid Analogue ◽  
Benzene Removal

The synthesis of a possible intermediate in phosphonolipid metabolism, viz. L-α-glyceryl-(2-trimethylammoniumethyl)phosphonate, a phosphonic acid analogue of L-α-glycerylphosphorylcholine, is described. The compound was obtained by condensation of D-acetone glycerol with (2-bromoethyl)metaphosphonate in boiling benzene, removal of the acetone group of the condensation product by acid hydrolysis, treatment of the hydrolysis product in dimethylformamide with trimethylamine at 60–62° for 3 days, isolation of L-α-glyceryl-(2-trimethylammoniumethyl)phosphate as cadmium chloride complex. Removal of the cadmium chloride was effected with a mixture of Amberlites IR-45 and IRC-50. A procedure for the preparation of (2-bromoethyl)metaphosphonate is reported.

Synthesis of Glycerol-1,3-diphosphonic Acid

1973 ◽  
Vol 51 (8) ◽  
pp. 1203-1205 ◽  
Author(s):  
Ranga Robinson ◽  
Erich Baer
Keyword(s):  
Acid Hydrolysis ◽  
Phosphonic Acid ◽  
Hydrobromic Acid ◽  
Condensation Product ◽  
Triethyl Phosphite ◽  
Phosphate Esters ◽  
Glyceric Acid ◽  
Diphosphonic Acid ◽  
Naturally Occurring ◽  
Acid Analogue

The synthesis of glycerol-1,3-diphosphonic acid, the phosphonic acid analogue of the naturally occurring glycerol-1,3-diphosphoric acid, is described. The phosphonic acid analogue was obtained in an overall yield of 29.7%, by heating a mixture of 1,3-dibromo-2-hexadecanoyloxypropane and triethyl phosphite to 140° for 48 h, distilling off in vacuo the excess of triethyl phosphite, hydrolyzing the condensation product, 1,3-bis(diethylphosphono)-2-hexadecanoyloxypropane, with 2 N hydrobromic acid at 100° for 5 h, and isolating the glycerol-1,3-diphosphonic acid in form of the dibarium salt. The glycerol-1,3-diphosphonate differs from glycerol-1,3-diphosphate and other phosphate esters of glycerol and glyceric acid by its greater stability towards acid hydrolysis. The glycerol-1,3-diphosphonic acid is readily distinguished from glycerol-1,3-diphosphoric acid and glycerol-1,2-diphosphoric acid by paper chromatography.

Isosteres of natural phosphates. 11. Synthesis of a phosphonic acid analogue of an oligonucleotide

Tetrahedron ◽  
1984 ◽  
Vol 40 (20) ◽  
pp. 3949-3956 ◽  
Author(s):  
Adam Mazur ◽  
Burton E. Tropp ◽  
Robert Engel
Keyword(s):  
Phosphonic Acid ◽  
Acid Analogue

Phosphonolipids 4. A phosphonic acid analogue of platelet activating factor

1993 ◽  
Vol 71 (2) ◽  
pp. 206-209 ◽  
Author(s):  
Yue-jin Liu ◽  
Burton E. Tropp ◽  
Robert Engel
Keyword(s):  
Phosphonic Acid ◽  
Platelet Activating Factor ◽  
Acid Analogue

A phosphonic acid analogue of platelet activating factor (PAF) bearing a backbone that is isosteric with and has stereochemistry corresponding to that of natural PAF has been synthesized. The synthesis uses a route maintaining stereochemical integrity.

Phosphonic acid analogues of carbohydrate metabolites. I. Synthesis of L- and D-dihydroxypropylphosphonic acid

1969 ◽  
Vol 47 (10) ◽  
pp. 955-960 ◽  
Author(s):  
Erich Baer ◽  
Hemendra Basu
Keyword(s):  
Propylene Glycol ◽  
Phosphonic Acid ◽  
Cold Water ◽  
Condensation Product ◽  
Triethyl Phosphite ◽  
Hot Water ◽  
Diethyl Ester ◽  
Mineral Acids ◽  
Optical Rotations ◽  
Carbohydrate Metabolites

A synthesis of the phosphonic acid analogues of L-α- and D-α-glycerophosphoric acid, viz. L- and D-dihydroxypropylphosphonic acid, is described. The L-dihydroxypropylphosphonic acid was obtained by treating acetone α-iodo-L-propylene glycol with triethyl phosphite at 120–125° for 24 h, hydrolyzing the condensation product acetone L-dihydroxypropylphosphonic acid diethyl ester with 2 N sulfuric acid at 100° for 48 h, and isolating the L-dihydroxypropylphosphonic acid as barium salt. The D-dihydroxypropylphosphonic acid was prepared in the same manner from acetone α-iodo-D-propylene glycol. The barium salts are readily soluble in cold water, much less soluble in hot water, and insoluble in the more common organic solvents. Dihydroxypropylphosphonic acid and α-glycerophosphoric acid can be distinguished from each other by their different behaviors towards hot mineral acids, and by the infrared spectra, n.m.r. spectra, and optical rotations of their barium salts.

An unsaturated phosphonic acid analogue of phosphatidylethanolamine and its activity in blood-clotting systems

Lipids ◽  
1968 ◽  
Vol 3 (3) ◽  
pp. 234-238 ◽  
Author(s):  
D. L. Turner ◽  
M. J. Silver ◽  
R. R. Holburn ◽  
E. Baczynski ◽  
Ann Brooker Brown
Keyword(s):  
Phosphonic Acid ◽  
Blood Clotting ◽  
Unsaturated Phosphonic Acid ◽  
Acid Analogue
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