Isolation of Rhodococcus sp. strain ECU0066, a new sulfide monooxygenase-producing strain for asymmetric sulfoxidation

Applied and Environmental Microbiology

Volumn 75, Issue 2, 2009, Pages 551-556

  Li, Ai Tao ^a   Zhang, Jian Dong ^a   Xu, Jian He ^a   Lu, Wen Ya ^b   Lin, Guo Qiang ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESES; BACTERIAL STRAINS; ENANTIOMERIC EXCESSES; ENANTIOSELECTIVE OXIDATIONS; MONOOXYGENASE; RHODOCOCCUS SP.; SULFOXIDATION;

BIOCHEMICAL ENGINEERING; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; ENZYMES; OCEANOGRAPHIC EQUIPMENT; SULFUR COMPOUNDS;

ENZYME ACTIVITY;

BACTERIUM; ENZYME ACTIVITY; OXIDATION; SULFIDE;

DNA, BACTERIAL; DNA, RIBOSOMAL; GENES, RRNA; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; OXIDOREDUCTASES ACTING ON SULFUR GROUP DONORS; RHODOCOCCUS; RNA, BACTERIAL; RNA, RIBOSOMAL, 16S; SEQUENCE ANALYSIS, DNA; SEQUENCE HOMOLOGY, NUCLEIC ACID; STEREOISOMERISM; SULFOXIDES;

BACTERIA (MICROORGANISMS); RHODOCOCCUS SP.;

EID: 58149379414     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.01527-08     Document Type: Article

References (25)

1. Adam, W., M. N. Korb, K. J. Roschmann, and C. R. Saha-Möller. 1998. Titanium-catalyzed, asymmetric sulfoxidation of alkyl aryl sulfides with optically active hydroperoxides. J. Org. Chem. 63:3423-3428.
2. Beer, J., P. Richardson, and A. Willetts. 1994. Baeyer-Villiger monooxygenase-dependent biotransformations: stereospecific heteroatom oxidations by camphor-grown Pseudomonas putida to produce chiral sulfoxides. Biotechnol. Lett. 16:909-912.
3. Bénéchie, M., and F. Khuong-Huu. 1996. Total synthesis of (-)-Maytansinol. J. Org. Chem. 61:7133-7138.
4. Boyd, D. R., N. D. Sharma, S. A. Haughey, M. A. Kennedy, B. T. McMurray, G. N. Sheldrake, C. C. R. Allen, H. Dalton, and K. Sproule. 1998. Toluene and naphthalene dioxygenase-catalysed sulfoxidation of alkyl aryl sulfides. J. Chem. Soc. Perkin Trans. I 12:1929-1933.
5. Boyd, D. R., N. D. Sharma, N. Gunaratne, S. A. Haughey, M. A. Kennedy, J. F. Malone, C. C. R. Allen, and H. Dalton. 2003. Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation. Org. Biol. Chem. 1:984-994.
6. Brunel, J. M., P. Diter, M. Duetsch, and H. B. Kagan. 1995. Highly enantioselective oxidation of sulfides mediated by a chiral titanium complex. J. Org. Chem. 60:8086-8088.
7. Carreno, M. C. 1995. Applications of sulfoxides to asymmetric synthesis of biologically active compounds. Chem. Rev. 95:1717-1760.
8. Cheesman, M. J., M. B. Kneller, E. J. Kelly, S. J. Thompson, C. K. Yeung, D. L. Eaton, and A. E. Rettie. 2001. Purification and characterization of hexahistidine-tagged cyclohexanone monooxygenase expressed in Saccharomyces cerevisiae and Escherichia coli. Protein Expr. Purif. 21:81-86.
9. Dembitsky, V. M. 2003. Oxidation, epoxidation and sulfoxidation reactions catalysed by haloperoxidases. Tetrahedron 59:4701-4720.
10. Fernández, I., and N. Khiar. 2003. Recent developments in the synthesis and utilization of chiral sulfoxides. Chem. Rev. 103:3651-3705.
11. Folsom, B. R., D. R. Schieche, P. M. Digrazia, J. Werner, and S. Palmer. 1999. Microbial desulfurization of alkylated dibenzothiophenes from a hydrodesulfurized middle distillate by Rhodococcus erythropolis I-19. Appl. Environ. Microbiol. 65:4967-4972.
12. Holland, H. L., L. J. Allen, M. J. Chernishenko, M. Diez, A. Kohl, J. Ozog, and J. X. Gu. 1997. Side chain oxidation of aromatic compounds by fungi. 7. A rationale for sulfoxidation, benzylic hydroxylation, and olefin oxidation by Mortierella isabellina. J. Mol. Catal. B 3:311-324.
13. Holland, H. L., F. M. Brown, A. Kerridge, P. Penkos, and J. Arensdor. 2003. Biotransformation of sulfides by Rhodococcus erythropolis. J. Mol. Catal. B 22:219-223.
14. Kamerbeek, N. M., A. J. J. Olsthoorn, M. W. Fraaije, and D. B. Janssen. 2003. Substrate specificity and enantioselectivity of 4-hydroxyacetophenone monooxygenase. Appl. Environ. Microbiol. 69:419-426.
15. Kelly, D. R., C. J. Knowles, J. G. Mahdi, I. N. Taylor, and M. A. Wright. 1996. The enantioselective oxidation of sulfides to sulfoxides with Acinetobacter sp. NCIMB 9871, Pseudomonas sp. NCIMB 9872, Xanthobacter autotrophicus DSM 731 (NCIMB 10811) and the Black yeast NV-2. Tetrahedron Asymmetry 7:365-368.
16. Kirimura, K., T. Furuya, R. Sato, Y. Ishii, K. Kino, and S. Usami. 2002. Biodesulfurization of naphthothiophene and benzothiophene through selective cleavage of carbon-sulfur bonds by Rhodococcus sp. strain WU-K2R. Appl. Environ. Microbiol. 68:3867-3872.
17. Legros, J., J. R. Dehli, and C. Bolm. 2005. Applications of catalytic asymmetric sulfide oxidations to the syntheses of biologically active sulfoxides. Adv. Synth. Catal. 347:19-31.
18. Mata, E. G. 1996. Recent advances in the synthesis of sulfoxides from sulfides. Phosphorus 117:231-286.
19. Nakamura, S., Y. Watanabe, and T. Toru. 2000. Extremely efficient chiral induction in conjugate additions of p-tolyl α-lithio-β- (trimethylsilyl)ethyl sulfoxide and subsequent electrophilic trapping reactions. J. Org. Chem. 65:1758-1766.
20. Pasta, P., G. Carrea, H. L. Holland, and S. Dallavalle. 1995. Synthesis of chiral benzyl alkyl sulfoxides by cyclohexanone monooxygenase from Acinetobacter NCIMB 9871. Tetrahedron Asymmetry 6:933-936.
21. Pinedo-Rivilla, C., J. Aleu, and I. G. Collado. 2007. Enantiomeric oxidation of organic sulfides by the filamentous fungi Botrytis cinerea, Eutypa lata and Trichoderma viride. J. Mol. Catal. B 49:18-23.
22. Ricci, L. C., J. V. Comasseto, L. H. Andrade, M. Capelari, Q. B. Cass, and A. L. M. Porto. 2005. Biotransformations of aryl alkyl sulfides by whole cells of white-rot Basidiomycetes. Enzyme Microb. Technol. 36:937-946.
23. Umemura, K., H. Matsuyama, N. Watanabe, M. Kobayashi, and N. Kamigata. 1989. Asymmetric alkylation of β-keto esters with optically active sulfonium salts. J. Org. Chem. 54:2374-2383.
24. Zambianchi, F., M. W. Fraaije, G. Carrea, G. Gonzalo, C. Rodríguez, V. Gotor, and G. Ottolina. 2007. Titration and assignment of residues that regulate the enantioselectivity of phenylacetone monooxygenase. Adv. Synth. Catal. 349:1327-1331.
25. Zhang, Q., and Y. K. Wu. 2007. Further explorations on bridged 1,2,4-trioxanes. Tetrahedron 63:10189-10201.