Process for preparing 1,2-diacyl-3-glycerylphosphorylcholines

Details Process for preparing 1,2-diacyl-3-glycerylphosphorylcholines Process for preparing 1,2-diacyl-3-glycerylphosphorylcholines

1976-01-26

1978-12-19

McCarthy, Helen M.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2523011R, 25231N, 252438, 252476, A23J 700

Patent

active

041305710

ABSTRACT:
Improved process for preparing 1,2-diacyl-3-glycerylphosphorylcholines, wherein the diacyl groups are, different or the same, a residue of a saturated or unsaturated fatty acid, particularly one of the acyl groups being a residue of a highly unsaturated fatty acid or being a residue of a saturated or unsaturated fatty acid labelled with an isotope, which comprises acylating a glyceryl-phosphorylcholine or monoacyl derivative thereof or the salt thereof with an acylating agent (e.g. 1-acylimidazole or 4-acyl-3-phenyl-1,2,4-oxadiazol-5-one) in the presence of a catalyst (e.g. an alkali salt of a nitrogen-containing 5-membered heterocyclic compound or sodium oxide).

REFERENCES:
patent: 3270084 (1966-08-01), Schriesheim et al.
patent: 3592829 (1971-07-01), Betzing
Slotboom, A. J. et al., "Hydrolysis of Phosphoglycerides by Purified Lipase Preparations. Preparation of Unsaturated 2-monoacylocholine Phosphoglycerides" Chem. Phys. Lipids, vol. 4, pp. 30-36 (1970).
Boss, W. F. et al., "Novel Synthesis of Spin Label Derivatives of Phosphatidylcholine" Anal. Biochem 64 (1) 1975, pp. 289-292.
Foerst, W. - Newer Methods of Preparative Organic Chemistry - vol. V, 1968, Academic Press NYC., "Syntheses Using Heterocyclic Amides (Azolides), pp. 61-63, pp. 74-77, 91.
Pugh, E. L. et al., "Simplified Procedure for Synthesis of Diacyl Carbon-labeled Lecithins"- J. Lipid Res. 16 (5) 1975, pp. 392-394.

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