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Enzymatic Alkylenation of Phospholipid Fatty Acid Chains by Extracts of Mycobacterium phlei

From the ¹ From the Department of Biochemistry, University of Chicago, Chicago, Illinois 60637

The enzymatic synthesis of tuberculostearic acid (10-methylstearic acid) was catalyzed by extracts of Mycobacterium phlei. This process involved two reactions of the olefinic fatty acid chain of phospholipids. The chain was first alkylenated at the 10-carbon to give a methylene group, which was subsequently reduced to a methyl group. The first reaction could be measured by using S-adenosylmethionine-methyl-¹⁴C. The enzyme was found in the supernatant fraction when extracts of cells broken by sonic oscillation were subjected to centrifugation at 100,000 x g. S-Adenosyl-l-methionine was the only effective donor of the 1-carbon unit. Phosphatidylglycerol, phosphatidylinositol, and phosphatidylethanolamine were substrates for the reaction, and both 16- and 18-carbon chains were alkylenated although only the 9-olefinic chains appeared to be converted. The enzyme acted upon chains at either position 1 or 2 of the glyceride molecule. Several detergents had little effect on the rate of the reaction.

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