Enzymic Oxidation of alcohols and aldehydes

摘要

1,153,151. Enzymic oxidation of alcohols and aldehydes. MOBIL OIL CORP. 6 June, 1966 [7 June, 1965], No. 25111/66. Heading C2C. Alcohols and aldehydes are enzymically oxidized to aldehydes and alkanoic acids respectively by a method comprising growing cells of a hydrocarbon-oxidizing micro-organism on a nutrient medium using a hydrocarbon having substantially the same number of carbon atoms as the starting alcohol or aldehyde as the sole source of carbon, harvesting the cells and rupturing the same in an aqueous medium, extracting from the cells a crude aqueous enzyme extract, optionally isolating from said crude extract an enzyme having specificity for the starting alcohol or aldehyde, mixing the crude extract or the isolated enzyme with the alcohol or aldehyde, incubating the mixture in the presence of molecular oxygen, DPNH oxidase and a sufficient amount of DPN+ oxidase to enzymically oxidize the alcohol or aldehyde to product aldehyde or alkanoic acid containing the same number of carbon atoms as the starting material, and at the same time reducing DPN + cofactor to reduced cofactor DPNH from which DPN+ is regenerated by DPNH oxidase to maintain amounts of DPN+ in the incubating mixture. The enzymes induced by growing cells on, e.g., a C 10 hydrocarbon exhibit specificity for oxidizing C 8-12 aldehydes and alcohols. The crude enzyme extract contains DPN+ and DPNH oxidase but addition from a commercial source may be required; an alternative source of addition DPN+ and DPNH oxidase is from cells grown on a non-hydrocarbon carbon source, e.g. glucose. The crude enzyme extract may contain enzymes which control the oxidation of hydrocarbons, alcohols, aldehydes and alkanoic acids and the required enzymes may be isolated, e.g. chromatographically. Such isolation removes DPN+ and DPNH oxidase from the enzyme and these must be supplied from a different source. Examples relate to the use of enzymes isolated from Achromobacter sp. grown on decane to oxidize decanol to decanal and decanal to decanoic acid. Other enzymes isolated from the crude mixture can be used to oxidize decane to the decanol starting material. The process is illustrated by reference to flow diagrams (not shown).