Biotransformation of β-ketosulfides to produce chiral β-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 reduc...

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Veröffentlicht in:	Journal of industrial microbiology & biotechnology 2003-05, Vol.30 (5), p.292-301
Hauptverfasser:	HOLLAND, H. L, BROWN, F. M, BARRETT, F, FRENCH, J, JOHNSON, D. V
Format:	Artikel
Sprache:	eng
Schlagworte:	Biological and medical sciences Biotransformation Fundamental and applied biological sciences. Psychology Fungi - metabolism Helminthosporium - metabolism Helminthosporium isabellina Magnetic Resonance Spectroscopy Mass Spectrometry Mortierella - metabolism Oxidation-Reduction Rhodococcus - metabolism Rhodococcus erythropolis Stereoisomerism Sulfides - metabolism Sulfoxides - metabolism
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Beschreibung
Zusammenfassung:	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.
ISSN:	1367-5435 1476-5535
DOI:	10.1007/s10295-003-0050-4