Literature DB >> 12759809

Biotransformation of beta-ketosulfides to produce chiral beta-hydroxysulfoxides.

H L Holland1, F M Brown, F Barrett, J French, D V Johnson.   

Abstract

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.

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Year:  2003        PMID： 12759809     DOI： 10.1007/s10295-003-0050-4

Source DB:  PubMed          Journal:  J Ind Microbiol Biotechnol        ISSN： 1367-5435            Impact factor:   3.346


  10 in total

Review 1.  Biodesulfurization.

Authors:  B L McFarland
Journal:  Curr Opin Microbiol       Date:  1999-06       Impact factor: 7.934

Review 2.  Enzymatic hydroxylation reactions.

Authors:  H L Holland; H K Weber
Journal:  Curr Opin Biotechnol       Date:  2000-12       Impact factor: 9.740

Review 3.  Aromatic dioxygenases: molecular biocatalysis and applications.

Authors:  D R Boyd; N D Sharma; C C Allen
Journal:  Curr Opin Biotechnol       Date:  2001-12       Impact factor: 9.740

Review 4.  Biotransformation of organic sulfides.

Authors:  H L Holland
Journal:  Nat Prod Rep       Date:  2001-04       Impact factor: 13.423

5.  Asymmetric Baeyer-Villiger oxidations of 4-mono- and 4,4-disubstituted cyclohexanones by whole cells of engineered Escherichia coli.

Authors:  M D Mihovilovic; G Chen; S Wang; B Kyte; F Rochon; M M Kayser; J D Stewart
Journal:  J Org Chem       Date:  2001-02-09       Impact factor: 4.354

6.  The reaction of S-benzylisothiourea with phenacyl bromide.

Authors:  R M DODSON
Journal:  J Am Chem Soc       Date:  1948-08       Impact factor: 15.419

7.  Elucidation of the metabolic pathway for dibenzothiophene desulphurization by Rhodococcus sp. strain IGTS8 (ATCC 53968).

Authors:  C Oldfield; O Pogrebinsky; J Simmonds; E S Olson; C F Kulpa
Journal:  Microbiology (Reading)       Date:  1997-09       Impact factor: 2.777

8.  Microbial desulfurization of alkylated dibenzothiophenes from a hydrodesulfurized middle distillate by Rhodococcus erythropolis I-19.

Authors:  B R Folsom; D R Schieche; P M DiGrazia; J Werner; S Palmer
Journal:  Appl Environ Microbiol       Date:  1999-11       Impact factor: 4.792

9.  Microbial oxidation of adamantanone by Pseudomonas putida carrying the camphor catabolic plasmid.

Authors:  S A Selifonov
Journal:  Biochem Biophys Res Commun       Date:  1992-08-14       Impact factor: 3.575

10.  Enzyme-catalysed oxygenation and deoxygenation routes to chiral thiosulfinates.

Authors:  Derek R Boyd; Narain D Sharma; Martina A Kennedy; Steven D Shepherd; John F Malone; André Alves-Areias; Robert Holt; Stig G Allenmark; Malin A Lemurell; Howard Dalton; Heather Luckarift
Journal:  Chem Commun (Camb)       Date:  2002-07-21       Impact factor: 6.222
  10 in total
  1 in total

1.  Atom-efficient gold(I)-chloride-catalyzed synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols: substrate scope and experimental and theoretical mechanistic investigation.

Authors:  Srijit Biswas; Christian Dahlstrand; Rahul A Watile; Marcin Kalek; Fahmi Himo; Joseph S M Samec
Journal:  Chemistry       Date:  2013-11-22       Impact factor: 5.236
  1 in total

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