THE PREPARATION OF L-α-GLYCERYLPHOSPHORYLCHOLINE FROM LECITHINS

Investigation of the hydrolysis of phosphatidylcholines (lecithins) in hot aqueous alcohol under the influence of mercuric chloride has shown that glycerylphosphorylcholine is formed and that neither racemization nor migration of the phosphorylcholine moiety occurs. The fatty acids are split off much more rapidly than is choline and as a consequence appreciable amounts of glycerylphosphorylcholine are formed. On the basis of these observations a procedure was devised for the hydrolysis of crude lecithin and the isolation of glycerylphosphorylcholine in a yield of 69%. The product was identified as L-α-glycerylphosphorylcholine by analysis of its cadmium chloride complex, and comparison of its optical rotation with that of the synthetic compound of known configuration. Recovery of the diester from this complex was accomplished through removal of the inorganic salt by ion-exchange resins and the free L-α-glycerylphosphorylcholine was crystallized from 99% ethanol.

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THE PREPARATION OF L-α-GLYCERYLPHOSPHORYLCHOLINE FROM LECITHINS

Canadian Journal of Biochemistry and Physiology ◽

10.1139/o55-093 ◽

1955 ◽

Vol 33 (5) ◽

pp. 761-766 ◽

Cited By ~ 11

Author(s):

N. H. Tattrie ◽

C. S. McArthur

Keyword(s):

Cadmium Chloride ◽

Inorganic Salt ◽

Optical Rotation ◽

Chloride Complex ◽

Ion Exchange Resins ◽

Aqueous Alcohol ◽

Synthetic Compound ◽

Exchange Resins ◽

Hydrolysis Of ◽

Crude Lecithin

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295. Ion-exchange resins as catalysts in the hydrolysis of esters

Journal of the Chemical Society (Resumed) ◽

10.1039/jr9520001607 ◽

1952 ◽

pp. 1607 ◽

Cited By ~ 45

Author(s):

C. W. Davies ◽

G. Garrod Thomas

Keyword(s):

Ion Exchange ◽

Ion Exchange Resins ◽

Exchange Resins ◽

Hydrolysis Of Esters ◽

Hydrolysis Of

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CuII—diamine complex catalyzed hydrolysis of phosphate triesters adsorbed on strong-base ion exchange resins. 31P NMR relaxation measurements

Journal of Molecular Catalysis ◽

10.1016/0304-5102(94)00094-8 ◽

1994 ◽

Vol 93 (2) ◽

pp. 221-231 ◽

Cited By ~ 7

Author(s):

W.T. Beaudry ◽

G.W. Wagner ◽

J.R. Ward

Keyword(s):

Ion Exchange ◽

31P Nmr ◽

Nmr Relaxation ◽

Ion Exchange Resins ◽

Strong Base ◽

Relaxation Measurements ◽

Exchange Resins ◽

Hydrolysis Of

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Synthesis of anisomycin. Part I. The stereospecific synthesis of N-benzoyl-2-(p-methoxybenzyl)-3-hydroxy-4-carboxamido pyrrolidine and the absolute configuration of anisomycin

Canadian Journal of Chemistry ◽

10.1139/v68-184 ◽

1968 ◽

Vol 46 (7) ◽

pp. 1101-1104 ◽

Cited By ~ 12

Author(s):

C. M. Wong

Keyword(s):

Infrared Spectra ◽

Absolute Configuration ◽

Optical Rotation ◽

Specific Rotation ◽

Stereospecific Synthesis ◽

Specific Optical Rotation ◽

Synthetic Compound ◽

The Absolute ◽

Hydrolysis Of ◽

Absolute Stereochemistry

L-Tyrosine was converted stereospecifically to N-benzoyl-2-(p-methoxybenzyl)-3-hydroxy-4-cyanopyrrolidine (10) which had a specific optical rotation [Formula: see text]. Anisomycin was converted also to N-benzoyl-2-(p-methoxybenzyl)-3-hydroxy-4-cyanopyrrolidine (16) which had a specific rotation [Formula: see text]. The infrared spectra of the synthetic compound and the derivative of anisomycin were superimposable with each other. This result showed that the absolute configuration of the three asymmetric centers in (10) of synthetic origin were 2S, 3S, 4S, and those in (16) were 2R, 3R, 4R. Thus, anisomycin should have the absolute stereochemistry 2R, 3S, 4S as depicted in the structure (2). Hydrolysis of the hydroxy nitriles (8) and (10) gave an identical amide (3) which should have the absolute stereochemistry 2S, 3S, 4R as shown in structure (3).

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