Biotransformation of beta-ketosulfides to produce chiral beta-hydroxysulfoxides.
The biotransformations of a series of substituted phenylthio-2-propanone and benzylthio-2-propanone were carried out using Helminthosporium sp. NRRL 4671, Mortierella isabellina ATCC 42613, or Rhodococcus erythropolis IGTS8. Several products gave microbial oxidation of sulfide to sulfoxide and reduction of carbonyl to secondary alcohol, producing beta-hydroxysulfoxides in medium to high enantiomeric and diastereomeric purities. Fungal biotransformations using Helminthosporium sp. and M. isabellina resulted in the opposite sulfoxide configurations of various beta-hydroxysulfoxide products.
Holland
H L
HL
Department of Chemistry, Brock University, ON L2S 3A1, St. Catharines, Canada. holland@chemiris.labs.brocku.ca
Brown
F M
FM
Barrett
F
F
French
J
J
Johnson
D V
DV
D001711:Biotransformation; D005658:Fungi / Q000378:metabolism*; D006375:Helminthosporium / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D020094:Mortierella / Q000378:metabolism; D010084:Oxidation-Reduction; D012240:Rhodococcus / Q000378:metabolism*; D013237:Stereoisomerism; D013440:Sulfides / Q000378:metabolism*; D013454:Sulfoxides / Q000378:metabolism*
D013440:Sulfides; D013454:Sulfoxides