Biotechnological production of chiral organic sulfoxides: Current state and perspectives

Applied Microbiology and Biotechnology

Volumn 98, Issue 18, 2014, Pages 7699-7706

  Matsui, Toru ^a,d   Dekishima, Yasumasa ^b   Ueda, Makoto ^c  

^a UNIVERSITY OF THE RYUKYUS   (Japan)

^b MITSUBISHI CHEMICAL CORPORATION   (Japan)

^c OYAMA NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^d TOKYO UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric synthesis; Bioconversion; Organic sulfoxide; Oxygenase; Peroxidase

Indexed keywords

BIOCHEMICAL ENGINEERING; BIOCONVERSION; BIOTECHNOLOGY; PLANTS (BOTANY); REACTION INTERMEDIATES; SULFUR COMPOUNDS;

ASYMMETRIC SYNTHESIS; BAEYER-VILLIGER MONOOXYGENASES; BIOTECHNOLOGICAL PRODUCTION; ORGANIC SULFOXIDE; OXYGENASES; PEROXIDASE; PROTON PUMP INHIBITORS; STEREOSELECTIVE OXIDATIONS;

ENZYMES;

CHIRAL ORGANIC SULFOXIDE; DIOXYGENASE; ENZYME; SULFOXIDE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; MIXED FUNCTION OXIDASE; PEROXIDASE;

BIOENGINEERING; BIOTECHNOLOGY; DRUG; ENZYME ACTIVITY; INHIBITOR; OXIDE; RESOLUTION;

BIOCATALYST; BIOPROCESS; BIOTECHNOLOGICAL PRODUCTION; CATALYSIS; CHIRALITY; PROCESS DEVELOPMENT; PROTEIN ENGINEERING; SHORT SURVEY; STEREOCHEMISTRY; WHOLE CELL; BIOTECHNOLOGY; METABOLISM; OXIDATION REDUCTION REACTION;

BIOTECHNOLOGY; MIXED FUNCTION OXYGENASES; OXIDATION-REDUCTION; PEROXIDASE; SULFOXIDES;

EID: 84906948397     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-014-5932-z     Document Type: Short Survey

References (52)

1. Adam W, Mock-Knoblauch C, Saha-Moller CR (1999) Asymmetric synthesis with the enzyme coprinus peroxidase: kinetic resolution of chiral hydroperoxides and enantioselective sulfoxidation. J Org Chem 64:4834-4839
2. Allenmark SG, Andersson MA (1996) Chloroperoxidase-catalyzed asymmetric synthesis of a series of aromatic cyclic sulfoxides. Tetrahedron: Asymmetry 7:1089-1094 (Pubitemid 26150541)
3. Balke K, Kadow M, Mallin H, Sass S, Bornscheuer UT (2012) Discovery, application and protein engineering of Baeyer-Villiger monooxygenases for organic synthesis. Org Biomol Chem 10:6249-6265
4. Benoit E, Cresteil T, Riviere JL, Delatour P (1992) Specific and enantioselective sulfoxidation of an aryl-trifluoromethyl sulfide by rat liver cytochromes P-450. Drug Metab Dispos 20:877881
5. Bong YK, Clay MD, Collier SJ, Mijts B, Vogel M, Zhang X, Zhu J, Nazor J, Smith D, Song S (2011) Synthesis of prazole compounds. WO071982
6. Bornscheuer UT, Huisman G, Kazlauskas RJ, Lutz S, Moore J, Robins K (2012) Engineering the third wave in biocatalysis. Nature 485:185-194
7. Boyd DR, Sharma ND, Haughey SA, Kennedy MA, McMurray BT, Sheldrake GN, Allen CCR, Dalton H, Sproule K (1998) Toluene and naphthalene dioxygenase-catalysed sulfoxidation of alkyl aryl sulfides. J Chem Soc, Perkin Trans 1:1929-1934
8. Burgess K, Henderson I (1989) A facile route to homochiral sulfoxides. Tetrahedron Lett 30:3633-3636
9. Buronfosse T, Moroni P, Benoit E, Riviere JL (1995) Stereoselective sulfoxidation of the pesticide methiocarb by flavin-containing monooxygenase and cytochrome P450-dependent monooxygenases of rat liver microsomes. Anticholinesterase activity of the two sulfoxide enantiomers. J Biochem Toxicol 10:179-189
10. Carrea G, Redigolo B, Riva S, Colonna S, Gaggero N, Battisterl E, Bianchi D (1992) Effects of substrate structure on the enantioselectivity and stereochemical course of sulfoxidation catalyzed by cyclohexanone monooxygenase. Tetrahedron: Asymmetry 3:1063-1068
11. Carreño MC (1995) Applications of sulfoxides to asymmetric synthesis of biologically active compounds. Chem Rev 95:6129-6144
12. Colonna S, Gaggero N, Manfredi A (1990) Enantioselective oxidations of sulfides catalyzed by chloroperoxidase. Biochemistry 29:10465-10468
13. Colonna S, Gaggero N, Casella L, Carrea G, Pasta P (1992) Chloroperoxidase and hydrogen peroxide: an efficient system for enzymatic enantioselective sulfoxidations. Tetrahedron: Asymmetry 3:95-106
14. Colonna S, Gaggero N, Pasta P, Ottolina G (1996) Enantioselective oxidation of sulfides to sulfoxides catalyzed by bacterial cyclohexanone monooxygenases. Chem Comm 20:2303-2307 (Pubitemid 126443703)
15. Colonna S, Gaggero N, Carrea G, Pasta P, Alphand V, Furstoss R (2001) Enantioselective synthesis of tert-butyl tert-butanethiosulfinate catalyzed by cyclohexanone monooxygenase. Chirality 13:40-42 (Pubitemid 32057998)
16. Dai L, Klibanov AM (2000) Peroxidase-catalyzed asymmetric sulfoxidation in organic solvents versus in water. Biotechnol Bioeng 70:353-357
17. Das PK, Caaveiro JM, Luque S, Klibanov AM (2002) Binding of hydrophobic hydroxamic acids enhances peroxidase's stereoselectivity in nonaqueous sulfoxidations. J Am Chem Soc 124:782-787 (Pubitemid 34112788)
18. de Gonzalo G, Pazmino DET, Ottolina G, Fraaije MW, Calaf E (2005) Oxidations catalyzed by phenylacetone monooxygenase from Thermobifida fusca. Tetrahedron: Asymmetry 16:3077-3083 (Pubitemid 41317549)
19. de Gonzalo G, Pazmino DET, Ottolina G, Fraaije MW, Carrea G (2006) 4-hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB as an oxidative biocatalyst in the synthesis of optically active sulfoxides. Tetrahedron: Asymmetry 17:130-135 (Pubitemid 43112324)
20. de Gonzalo G, Mihovilovic MD, Fraaije MW (2010) Recent developments in the application of Baeyer-Villiger monooxygenase as biocatalysts. Chembiochem 11:2208-2231
21. Dodson RM, Newman N, Tsuchiya HM (1962) Microbiological transformations. XI. The preparation of optically active sulfoxides. J Org Chem 27:2707-2708
22. Feingersch R, Shainsky J, Wood TK, Fishman A (2008) Protein engineering of toluene monooxygenases for synthesis of chiral sulfoxides. Appl Environ Microbiol 74:1555-1566 (Pubitemid 351358453)
23. Fraaije MW, Wu J, Heuts DP, van Hellemond EW, Spelberg JH, Janssen DB (2005) Discovery of a thermostable Baeyer-Villiger monooxygenase by genome mining. 66:393-400
24. Friemann R, Ivkovic-Jensen MM, Lessner DJ, Yu C-L, Gibson DT, Parales RE, Eklund H, Ramaswamy S (2005) Structural insight into the dioxygenation of nitroarene compounds: the crystal structure of nitrobenzene dioxygenase. J Mol Bio 348:1139-1151 (Pubitemid 40602372)
25. Harris RZ, Newmyer SL, Montellano PRO (1993) Horseradish peroxidase-catalyzed two-electron oxidations. J Biol Chem 25:1637-1645
26. Hibi M, Kawashima T, Kodera T, Smirnov SV, Sokolov PM, Sugiyama M, Shimizu S, Yokozeki K, Ogawa J (2011) Characterization of Bacillus thuringiensis L-isoleucine dioxygenase for production of useful amino acids. Appl Environ Microbiol 77:6926-6930
27. Hibi M, Kawashima T, Yajima H, Smirnov SV, Kodera T, Sugiyama M, Shimizu S, Yokozeki K, Ogawa J (2013) Enzymatic synthesis of chiral amino acid sulfoxides by Fe(II)/α-ketoglutarate-dependent dioxygenase. Tetrahedron: Asymmetry 24:990-994
28. Kamerbeek NM, Janssen DB, van Berkei WJH, Fraaije MW (2003) Baeyer-Villiger monooxygenases, an emerging family of flavin dependent biocatalysts. Adv Synth Catal 345:667-678 (Pubitemid 37406648)
29. Kielbasinski P, Rachwalski M, Mikolajczyk M, Rutjes MPJT (2008) Nitrilase-catalysed hydrolysis of cyanomethyl p-tolyl sulfoxide: stereochemistry and mechanism. Tetrahedron: Asymmetry 19:562-567
30. Klibanov AM (2001) Improving enzymes by using them in organic solvents. Nature 409:241-246
31. Lee K, Brand JM, Gibson DT (1995) Stereospecific sulfoxidation by toluene and naphthalene dioxygenases. Biochem Biophys Res Commun 212:9-15
32. Li AT, Zhang JD, Xu JH, Lu WY, Lin GQ (2009) Isolation of Rhodococcus sp. strain ECU0066, a new sulfide monooxygenase-producing strain for asymmetric sulfoxidation. Appl Environ Microbiol 75:551-556
33. Li A-T, Yu H-L, Pan J, Zhang J-D, Xu JH, Lin G-Q (2011) Resolution of racemic sulfoxides with high productivity and enantioselectivity by a Rhodococcus sp. strain as an alternative to biooxidation of prochiral sulfides for efficient production of enantiopure sulfoxides. Biores Technol 102:1537-1542
34. Light DR, Waxman DJ, Walsh C (1982) Studies on the chirality of sulfoxidation catalyzed by bacterial flavoenzyme cyclohexanone monooxygenase and hog liver flavin adenine dinucleotide containing monooxygenase. Biochemistry 21:2490-2498
35. Malito E, Alfieri A, Fraaije MW, Mattevi A (2004) Crystal structure of a Baeyer-Villiger monooxygenase. Proc Natl Acad Sci U S A 101:13157-13162 (Pubitemid 39209635)
36. Moroni P, Buronfosse T, Longin-Sauvageon C, Delatour P, Benoit E (1995) Chiral sulfoxidation of albendazole by the flavin adenine dinucleotide- containing and cytochrome P450-dependent monooxygenases from rat liver microsomes. Drug Metab Dispos 23:160-165
37. Nikodinovic-Runic J, Coulombel L, Francuski D, Sharma ND, Boyd DR, Ferrall RMO, O'Connor KE (2013) The oxidation of alkylaryl sulfides and benzo[b]thiophenes by Escherichia coli cells expressing wild-type and engineered styrene monooxygenase from Pseudomonas putida CA-3. Appl Microbiol Biotechnol 97:4849-4858
38. Ohshiro A, Izumi Y (1999) Microbial desulfurization of organic sulfur compounds in petroleum. Biosci Biotechnol Biochem 63:1-9
39. Opperman DJ, Reetz MT (2010) Towards practical Baeyer-Villiger- monooxygenases: Design of cyclohexanone monooxygenase mutants with enhanced oxidative stability. Chem Bio Chem 11:2589-2596
40. Parales RE, Lee K, Resnick SM, Jiang H, Lessner DJ, Gibson DT (2000) Substrate specificity of naphthalene dioxygenase: effect of specific amino acids at the active site of the enzyme. J Bact 182:1641-1649 (Pubitemid 30121129)
41. Parales RE, Huang R, Yu C-L, Parales JV, Lee FKN, Lessner DJ, Ivkovic-Jensen MM, Liu W, Friemann R, Ramaswamy S, Gibson DT (2005) Purification, characterization, and crystallization of the components of the nitrobenzene and 2-nitrotoluene dioxygenase enzyme systems. Appl Environ Microbiol 71:3806-3814 (Pubitemid 40980550)
42. Pazmiño DET, Snajdrova R, Rial DV, Mihovilovic MD, Fraaije MW (2007) Altering the substrate specificity and enantioselectivity of phenylacetone monooxygenase by structure-inspired enzyme redesign. Adv Synth Catal 349:1361-1368
43. Rachwalski M, Kwiatkwska M, Drabowicz J, Klos M, Wieczorek WM, Szyrej M, Sieron L, Kielbasinski P (2008) Enzyme-promoted desymmetrization of bis(2-hydroxymethylphenyl) sulfoxide as a route to tridentate chiral catalysts. Tetrahedron: Asymmetry 19:2096-2101
44. Ramadhan SH, Matsui T, Nakano K, Minami H (2012) High cell density cultivation of Pseudomonas putida strain HKT554 and its application for optically active sulfoxide production. Appl Microbiol Biotechnol 97:1903-1907
45. Rioz-Martinez A, Bisoqno FR, Rodriguez C, de Gonzalo G, Lavandera I, Pazmiño DET, Fraaije MW, Gotor V (2010) Biocatalyzed concurrent production of enantioenriched compounds through parallel interconnected kinetic asymmetric transformations. Org Biomol Chem 8:1431-1437
46. Schallmey A, den Besten G, Teune IG, Kembaren RF, Janssen DB (2011) Characterization of cytochrome P450 monooxygenase CYP154H1 from the thermophilic soil bacterium Thermobifida fusca. Appl Microbiol Biotechnol 89:1475-1485
47. Shainsky J, Bernath-Levin K, Isaschar-Ovdat S, Glaser F, Fishman A (2013) Protein engineering of nitrobenzene dioxygenase for enantioselective synthesis of chiral sulfoxides. Protein Eng Des Sel 26:1-11
48. ten Brink HB, Holland HL, Schoemaker HE, van Lingen H, Weber R (1999) Probing the scope of the sulfoxidation activity of vanadium bromoperoxidase from Ascophyllum nodosum. Tetrahedron: Asymmetry 10:4563-4572 (Pubitemid 30084679)
49. Toda H, Imae R, Itoh N (2012) Efficient biocatalyst for the production of enantiopure (S)-epoxides using a styrene monooxygenase (SMO) and Leifsonia alcohol dehydrogenase (LSADH) system. Tetrahedron: Asymmetry 23:1542-1549
50. Yoshida T, Kito M, Tsuji M, Nagasawa T (2001) Microbial synthesis of a proton pump inhibitor by enantioselective oxidation of a sulfide into its corresponding sulfoxide by Cunninghamella echinulata MK-40. Biotechnol Lett 23:1217-1222 (Pubitemid 32781189)
51. Yu JH, Klibanov AM (2006) Co-lyophilization with D-proline greatly enhances peroxidase's stereoselectivity in a non-aqueous medium. Biotechnol Lett 28:555-558
52. Zhai XH, Ma YH, Lay DY, Zhou S, Chen ZM (2013) Development of a whole-cell biocatalyst with NADPH regeneration system for biosulfoxidation. J Ind Microbiol Biotechnol 40:797-803