Fungal biotransformation of organophosphines.
1. The biotransformations of triphenyl phosphite and of triphenyl-, tri-n.-butyl-, diethylphenyl-, and ethylmethylphenyl-phosphines by the fungi Mortierella isabellina ATCC 42613, Helminthosporium species NRRL 4671, and Aspergillus foetidus ATCC 10254, have been examined. 2. The triaryl and tri-n.-butyl substrates underwent oxidation at phosphorus in low yield, a process attributed largely to auto-oxidation under the experimental conditions used. 3. The alkyl aryl phosphines were enzymically oxidized at phosphorus, but concurrent auto-oxidation also occurred. 4. Incubation of ethylmethylphenyl phosphine with M. isabellina gave the corresponding S(-) phosphine oxide in a 92% yield with an enantiomeric purity of 13%.
Holland
H L
HL
Department of Chemistry, Brock University, St. Catharines, Ontario, Canada.
Carey
M
M
Kumaresan
S
S
D001230:Aspergillus / Q000378:metabolism; D001711:Biotransformation; D005658:Fungi / Q000378:metabolism*; D006375:Helminthosporium / Q000378:metabolism; D009090:Mucorales / Q000378:metabolism; D009943:Organophosphorus Compounds / Q000378:metabolism*; D010084:Oxidation-Reduction
D009943:Organophosphorus Compounds