Abstract
AbstractAcyl coenzyme A analogues in which the sulphur is replaced by methylene are stable to hydrolysis and can be used to investigate enzymatic reaction mechanisms. With this idea in mind we synthesized isobutanoyl‐carba(dethia)‐coenzyme A (isobutanoyl‐CH2CoA) and monitored its reaction in enzymatic systems. A cell‐free extract of Pseudomonas putida (ATCC 21244) complemented with FAD, phenazine methosulphate, and DCIP catalyzed the conversion of isobutanoyl‐CH2CoA into methacryloyl‐CH2CoA and β‐hydroxyisobutanoyl‐CH2CoA. The latter could not be further oxidized to the aldehyde and carboxyl level, indicating that these oxidations normally occur after hydrolysis of the CoA ester.
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