PMID: 2860924Jul 9, 1985

Loss of stereospecificity of phospholipases C and D upon introduction of a 2-alkyl group into rac-1,2-diacylglycero-3-phosphocholine

Biochimica Et Biophysica Acta
M BugautJ J Myher

Abstract

rac-1-[1-14C]Lauroyl-2-oleylglycero-3-phospho[methyl-3H]choline and rac-1-lauroyl-2-[1-14C]oleoylglycero-3-phospho[methyl-3H]choline along with rac-1-palmitoyl-2-oleylglycero-3-phosphocholine and sn-1-palmitoyl-2-oleylglycero-3-phosphocholine were synthesized and subjected to hydrolysis with phospholipase C (EC 3.1.4.3) from Clostridium perfringens and phospholipase D (EC 3.1.4.4) from cabbage. Kinetics of hydrolysis of the radioactive substrates were determined by measuring the 3H radioactivity retained in the aqueous phase due to free choline and phosphocholine and the 3H and 14C radioactivity recovered in the organic phase due to the released diacylglycerols and phosphatidic acids and the residual phosphatidylcholines. The rate of hydrolysis of the unlabelled substrates by phospholipase C was determined by thin-layer chromatography and gas-liquid chromatography of the methanolysis products. The relative initial rates of hydrolysis of sn-1,2,- and sn-2,3-enantiomers were 100-200:1 for phospholipase C and 40-50:1 for phospholipase D using rac-1-lauroyl-2-oleoylglycero-3-phosphocholine as the substrate. The substitution of the 2-acyl group by an alkyl group resulted in a loss of stereospecificity, which was partial for phosphol...Continue Reading

References

Mar 1, 1978·Proceedings of the National Academy of Sciences of the United States of America·M B CableG L Powell
May 25, 1962·Biochemistry·E BAER, A KINDLER
Apr 1, 1962·Memphis and Mid-South Medical Journal·T C GLADDING

Related Concepts

Cauliflower (Dietary)
Carbon Radioisotopes
Clostridium perfringens
Phosphatidylcholines
Type C Phospholipases
Phospholipase D
Phospholipase
Radioisotope Dilution Technique
Substrate Specificity
Tritium

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