Oxidation ofn-Tetradecane and 1-Tetradecene by Fungi

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Abstract
Cunninghamella blakesleeana(minus strain) and aPenicilliumspecies were grown in a mineral-salts medium containing eithern-tetradecane or 1-tetradecene as substrate, and ether extracts of the mycelial mats were analyzed for oxidation products. Extracts fromCunninghamellarevealed tetradecanoic acid and 13-tetradecenoic acid from the oxidation ofn-tetradecane and 1-tetradecene, respectively, thereby indicating that these hydrocarbons were subject to methyl group oxidation. In contrast toCunninghamella, thePenicilliumoxidized the two substrates by subterminal attacks on methylene rather than methyl groups. This was evidenced by tentative identifications of the following alcohols and ketones from oxidation of the hydrocarbons: tetradecan-2-ol, dodecan-1-ol, tetradecan-2-one, and tetradecan-4-one fromn-tetradecane, and tetradecen-4-ol, 13-tetradecen-4-ol, tetradecen-3-ol, 13-tetradecen-4-one, and tetradecen-3-one from 1-tetradecene. A pathway for hydrocarbon oxidation is proposed for subterminal oxidation at the methylene alpha to the methyl group.

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