Abstract

The complete series of even- and odd-chain straight chain saturated fatty acid cholesterol esters were synthesized. Their melting points alternated in a fashion resembling that of the corresponding fatty acids. Rat liver cholesterol ester hydrolase (sterol ester hydrolase, EC 3.1.1.13) exhibited rates which were markedly dependent on the chain length of the fatty acid constituent. Most important, they were alternating with each one of the even-chain fatty acid cholesterol ester hydrolyzed at a higher rate than did the odd-chain ester containing either one more or one less carbon atom. Alternations in physical properties and in hydrolyzability are discussed in terms of tilting of the hydrocarbon chain with respect to the carboxyl group. It is suggested, that tilting gives rise to geometric differences which influence hydrocarbon chain interactions. In crystals they are reflected in melting points. In reaction rates they manifest themselves during the formation of the substrate-enzyme complex.

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