1887

Abstract

The enantioselective reduction of racemic sulfoxides by dimethyl sulfoxide reductases from and was investigated. Purified dimethyl sulfoxide reductase from catalysed the selective removal of -methyl -tolyl sulfoxide from a racemic mixture of methyl -tolyl sulfoxide and resulted in an 88% recovery of enantiomerically pure -methyl -tolyl sulfoxide. was shown to be able to grow photoheterotrophically in the presence of certain chiral sulfoxides under conditions where a sulfoxide is needed as an electron sink. Whole cells of were shown to catalyse the enantioselective reduction of methyl -tolyl sulfoxide, ethyl 2-pyridyl sulfoxide, methylthiomethyl methyl sulfoxide and methoxymethyl phenyl sulfoxide. Similarly, whole cells of and reduced these sulfoxides but with opposite enantioselectivity.

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/content/journal/micro/10.1099/00221287-144-8-2247
1998-08-01
2021-10-20
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References

  1. Abo M., Tachibana M., Okubo A., Yamazaki S. 1994; Enantioselective reduction of the sulfoxide to sulfide in methyl phenyl sulfoxide by dimethylsulfoxide reductase from Rhodo- bacter sphaeroides f.s. denitrificans. . Biosci Biotechnol Biochem 58:596–597
    [Google Scholar]
  2. Abo M., Tachibana M., Okubo A., Yamazaki S. 1995; Enantioselective deoxygenation of alkyl aryl sulfoxides by DMSO reductase from Rhodobacter sphaeroides f.s. denitrificans. . Bioorg Med Chem 3:109–112
    [Google Scholar]
  3. Bennett B., Benson N., McEwan A.G., Bray R.C. 1994; Multiple states of the molybdenum centre of dimethylsulfoxide reductase from Rhodobacter capsulatus revealed by EPR spectroscopy.. Eur J Biochem 225:321–331
    [Google Scholar]
  4. Benson N. 1993 Biochemical and spectroscopic studies of dimethylsulphoxide reductase from Rhodobacter capsulatus. PhD thesis University of East Anglia:
    [Google Scholar]
  5. Bevinakatti H.S., Banerji A.A. 1991; Practical chemo- enzymatic synthesis of both enantiomers of propanolol.. J Org Chem 56:5372–5375
    [Google Scholar]
  6. Blattner F.R. 3rd Bloch C.A. 14 other authors 1997; The complete genome sequence of Escherichia coli K-12.. Science 277:1453–1474
    [Google Scholar]
  7. Burgess K., Henderson I., Ho K.-K. 1992; Biocatalytic resolutions of sulfinylalkonoates: a facile route to optically active sulfoxides.. J Org Chem 57:1290–1295
    [Google Scholar]
  8. Butlin R.J., Linney I.D., Mahon M.F., Tye H., Wills M. 1996; Recoverable chiral sulfoxides for asymmetric synthesis: application to stereoselective carbonyl reduction and the asymmetric synthesis of allylic alcohols.. J Chem Soc Perkins Trans 1:95–105
    [Google Scholar]
  9. Carreno M.C. 1995; Applications of sulfoxides to asymmetric synthesis of biologically active compounds.. Chem Rev 95:1717–1760
    [Google Scholar]
  10. Colonna S., Gaggero N., Manfredi A., Caseiia L., Gullotti M., Carrea G., Pasta P. 1990; Enantioselective oxidations of sulfides catalysed by chlorperoxidase.. Biochemistry 29:10465–10468
    [Google Scholar]
  11. Crosby J. 1992; Chirality in industry - an overview.. In Chirality in Industry 1 pp. 1–66 Collins A.N., Sheldrake G.N., Crosby J. Edited by Chichester: Wiley;
    [Google Scholar]
  12. Hanlon S.P. 1993 Physiology and biochemistry of dimethyl- sulfide oxidation and dimethylsulfoxide reduction by Rhodobacter species. PhD thesis University of East Anglia:
    [Google Scholar]
  13. Holland H. L. 1988; Chiral sulfoxidation by biotransformation of organic sulfides.. Chem Rev 88473–485
    [Google Scholar]
  14. Holland H.L., Brown F.M., Larsen B.G. 1995; Biotrans-formation of organic sulfides. 6. Formation of chiral para substituted benzyl methyl sulfoxides by Helminthosporium species NRRL 4671.. Tetrahedron Asymmetry 6:1561–1567
    [Google Scholar]
  15. Hudig H., Kaufmann N., Drews G. 1986; Respiratory deficient mutants of Rhodopseudomonas capsulata. . Arch Microbiol 145:378–385
    [Google Scholar]
  16. Iobbi-Nivol C., Pommier J., Simala-Grant J., Mejean V., Giordano G. 1996; High substrate specificity and induction characteristics of trimethylamine-N-oxide reductase of Escherichia coli. . Biochim Biophys Acta 1294:77–82
    [Google Scholar]
  17. Jones R.W., Garland P.B. 1976; Sites and specificity of the reaction of bipyridylium compounds with anaerobic respiratory enzymes of Escherichia coli. Effects of permeability barriers imposed by the cytoplasmic membrane.. Biochem J 164:199–211
    [Google Scholar]
  18. McAlpine A.S., McEwan A.G., Shaw A.L., Bailey S. 1997; Molybdenum active centre of DMSO reductase from Rhodobacter capsulatus: crystal structure of the oxidised enzyme at 1·82 Å resolution and the dithionite-reduced enzyme at 2·8 Å resolution.. J Biol Inorg Cbem 2:690–701
    [Google Scholar]
  19. McAlpine A.S., McEwan A.G., Bailey S. 1998; The high resolution crystal structure of DMSO reductase in complex with DMSO.. J Mol Biol 275:613–623
    [Google Scholar]
  20. McEwan A.G. 1994; Photosynthetic electron transport and anaerobic metabolism in purple non-sulfur phototrophic bacteria.. Antonie Leeuwenhoek 66:151–164
    [Google Scholar]
  21. McEwan A.G., Wetzstein H.-G., Jackson J.B., Ferguson S.J. 1985; Periplasmic location of the terminal reductase in trime- thylamine-N-oxide and dimethylsulfoxide respiration in the photosynthetic bacterium Rhodopseudomonas capsulata. . Bio-cbirn Biophys Acta 806:410–417
    [Google Scholar]
  22. McEwan A.G., Ferguson S.J., Jackson J.B. 1991; Purification and properties of dimethylsulphoxide reductase from Rhodo- bacter capsulatus. . Biochem J 207:305–307
    [Google Scholar]
  23. Penzer G.R., Radda G.K. 1971; Photochemistry of flavins.. Methods Enzymol 18B:479–495
    [Google Scholar]
  24. Pitchen P., France C.J., McFarlane I.M., Newton C.G., Thompson D.M. 1994; Large scale synthesis of a biologically active sulfoxide.. Tetrahedron Lett 35:485–488
    [Google Scholar]
  25. Richardson D.J., King G.F., Kelly O.J., McEwan A.G., Jackson J.B., Ferguson S.J. 1988; The role of auxiliary oxidants in maintaining redox balance during phototrophic growth of Rhodobacter capsulatus on propionate and butyrate.. Arch Microbiol 150:130–137
    [Google Scholar]
  26. Roberts S.M., Turner N.J., Willets A.J., Turner M.K. 1995 Introduction to Biocatalysis Using Enzymes and Microorganisms. Cambridge: Cambridge University Press;
    [Google Scholar]
  27. Rossi G, Fauve A., Madesdaire M., Roche D., Davis F.A., Reddy R.T. 1992; Microbiological and chemical methods in the asymmetric oxidation of sulfides: a comparative study for the preparation of (S)-vinyl sulfoxides.. Tetrahedron Asymmetry 3:629–636
    [Google Scholar]
  28. Satoh T., Kurihara F.N. 1987; Purification and properties of dimethylsulfoxide reductase containing a molybdenum cofactor from a photodenitrifier, Rhodobacter sphaeroides f.s.denitri- ficans. . J Biochem 102:191–197
    [Google Scholar]
  29. Schindelin H., Kisker G, Hilton J. C., Rajagopalan K. V., Rees D.C. 1996; Crystal structure of DMSO reductase: redox-linked changes in molybdopterin coordination.. Science 272:1615–1621
    [Google Scholar]
  30. Schneider F., Lowe J., Huber J., Schindelin H., Kisker C., Knaeblein J. 1996; Crystal structure of dimethylsulfoxide reductase from Rhodobacter capsulatus at 1·88 Å resolution.. J Mol Biol 263:53–69
    [Google Scholar]
  31. Shaw A.L, Hanson G. R., McEwan A. G. . 1996; Cloning and sequence analysis of the dimethylsulfoxide reductase structural gene from Rhodobacter capsulatus. . Biochim Biophys Acta 1276:176–180
    [Google Scholar]
  32. Simala-Grant J.L., Weiner J.H. 1996; Kinetic analysis and substrate specificity of Escherichia coli dimethylsulfoxide reductase.. Microbiology 142:3231–3239
    [Google Scholar]
  33. Solladie G. 1981; Asymmetric synthesis using nucleophilic reagents containing a chiral sulfoxide group.. Synthesis 3:185–196
    [Google Scholar]
  34. Styrvold O.B., Strom A.R. 1984; Dimethylsulphoxide and trimethylamine-N-oxide respiration of Proteus vulgaris. . Arch Microbiol 140:74–78
    [Google Scholar]
  35. Weaver P.F., Wall J.D., Gest H. 1975; Characterisation of Rhodopseudomonas capsulata. . Arch Microbiol 105:207–216
    [Google Scholar]
  36. Weiner J., Maclsaac D.P., Bishop R.E., Bilous R.E. 1988; Purification and properties of dimethylsulfoxide reductase, an iron-sulfur molybdoenzyme of Escherichia coli. . J Bacteriol 170:1505–1510
    [Google Scholar]
  37. Weiner J., Rothery R.A., Sambasivarao D., Trieber C.A. 1992; Molecular analysis of dimethylsulfoxide reductase: a complex iron-sulfur molybdoenzyme of Escherichia coli. . Biochim Biophys Acta 1102:1–18
    [Google Scholar]
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