The formation of 1-hydroxymethylnaphthalene and 6-hydroxymethylquinoline by both oxidative and reductive routes in Cunninghamella elegans.
Extraction of medium after incubation of the fungus, Cunninghamella elegans, with 0.03% (w/v) 1-methylnaphthalene produced mainly 1-hydroxymethylnaphthalene together with some 1-naphthoic acid and hydroxynaphthoic acid. Higher concentrations of substrate were inhibitory to biotransformation. Similar incubations with 1-naphtoic acid as substrate resulted in reduction of the carboxyl group to give 1-hydroxymethylnaphthalene. When 6-methylquinoline was used, the main product was 6-hydroxymethylquinoline but also some quinoline-6-carboxylic acid and some 6-methylquinoline-N-oxide were identified. In a 2-l fermenter 2.5 g substrate was transformed in 324 h. The 6-hydroxymethylquinoline was also produced by reduction of quinoline-6-carboxylic acid by the organism.
Mountfield
R J
RJ
Institute of Biological Sciences, University of Wales, Aberystwyth, Ceredigion, UK. rmo@novo.dk
Hopper
D J
DJ
D001673:Biodegradation, Environmental; D002264:Carboxylic Acids / Q000378:metabolism; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D003470:Culture Media; D020093:Cunninghamella / Q000254:growth & development / Q000378:metabolism*; D013058:Mass Spectrometry; D009281:Naphthalenes / Q000378:metabolism*; D010084:Oxidation-Reduction; D011804:Quinolines / Q000378:metabolism*; D012989:Soil Pollutants / Q000378:metabolism; D014874:Water Pollutants, Chemical / Q000378:metabolism
C115831:1-hydroxymethylnaphthalene; C115830:6-hydroxymethylquinoline; D002264:Carboxylic Acids; D003470:Culture Media; D009281:Naphthalenes; D011804:Quinolines; D012989:Soil Pollutants; D014874:Water Pollutants, Chemical; C085312:1-naphthoic acid; C025968:1-methylnaphthalene