3.5.2 Oxidation at Sulfur

G. Grogan

doi:10.1055/sos-SD-216-00175

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Faber, K. et al.: 2015 Science of Synthesis: Biocatalysis in Organic Synthesis 3 DOI: 10.1055/sos-SD-216-00175

Biocatalysis in Organic Synthesis 3

3.5.2 Oxidation at Sulfur

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Editors: Faber, K.; Fessner, W.-D.; Turner, N. J.

Authors: Allen, C. C. R.; de Gonzalo, G.; Ellinger, J. J.; Ewing, T. A.; Faber, K.; Fernández-Lucas, J.; Flynn, C. M.; Fraaije, M. W.; García-Junceda, E.; Garrabou, X.; Gkotsi, D. S.; Glueck, S. M.; Goss, R. J. M.; Grogan, G.; Gröger, H.; Grüschow, S.; Hammer, S. C.; Hauer, B.; Herter, S.; Hilvert, D.; Hollmann, F.; Hormigo, D.; Hummel, W.; Molla, G.; Nestl, B. M.; Nolte, J. C.; Obexer, R.; Oroz-Guinea, I.; Patel, R. N.; Pollegioni, L.; Quin, M. B.; Schmidt-Dannert, C.; Smith, D. R. M.; Turner, N. J.; Urlacher, V. B.; van Berkel, W. J. H.; Woodley, J. M.

Title: Biocatalysis in Organic Synthesis 3

Print ISBN: 9783131746610; Online ISBN: 9783131974914; Book DOI: 10.1055/b-003-125814

1st edition © 2015. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries

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Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

The asymmetric biocatalytic oxidation of sulfides can be performed with high enantioselectivity by a number of different enzymes, allowing access to biologically active compounds including flavors and pharmaceuticals, and also chiral auxiliaries for organic synthesis. The application of biocatalysts in asymmetric sulfoxidation has benefited recently from advances in molecular biology that allow the study and application of individual enzymes, either purified or expressed in recombinant strains of E. coli. In this chapter, the major contemporary approaches to biocatalytic sulfoxidation, including enzymes such as peroxidases, flavin-dependent monooxygenases, and dioxygenases, are reviewed. In addition, the most user-friendly examples of enzyme-catalyzed sulfoxidation are illustrated using practical exemplar procedures from the relevant literature.

Key words

Baeyer–Villiger monooxygenase - bovine serum albumin - chloroperoxidase - cytochrome P450 - dioxygenase - flavin-containing monooxygenase - horseradish peroxidase - peroxidase - sulfide - sulfoxidation - sulfoxide - tyrosinase - vanadium bromoperoxidase

1 Bentley R. Chem. Soc. Rev. 2005; 34: 609

PubMed Search in Google Scholar

2 Solladie G. Heteroat. Chem. 2002; 13: 443

Search in Google Scholar

3 Legros J, Dehli JR, Bolm C. Adv. Synth. Catal. 2005; 347: 19

Search in Google Scholar

4 Kagan HB, Organosulfur Chemistry in Asymmetric Synthesis. Toru T, Bolm C. Wiley-VCH; Weinheim, Germany 2008: 1–29

Search in Google Scholar

5 Wojaczyńska E, Wojaczyński J. Chem. Rev. 2010; 110: 3851

PubMed Search in Google Scholar

6 Mahony GE, Ford A, Maguire AR. J. Sulfur Chem. 2013; 34: 301

Search in Google Scholar

7 Holland HL. Chem. Rev. 1988; 88: 473

Search in Google Scholar

8 Colonna S, Gaggero N, Pasta P, Ottolina G. Chem. Commun. (Cambridge) 1996; 2303

9 Holland HL. Nat. Prod. Rep. 2001; 18: 171

PubMed Search in Google Scholar

10 Grogan G, Comprehensive Chirality. Carreira EM, Yamamoto H. Elsevier; Amsterdam, Netherlands 2012. 7. 295–328

Search in Google Scholar

11 Dodson RM, Tsuchiya HM, Newman N. J. Org. Chem. 1962; 27: 2707

Search in Google Scholar

12 Auret BJ, Boyd DR, Henbest HB. Chem. Commun. 1966; 66

13 Auret BJ, Boyd DR, Henbest HB, Ross S. J. Chem. Soc. C 1968; 2371

14 Auret BJ, Boyd DR, Henbest HB, Watson CG, Balenovic K, Polak V, Johanides V, Divjak S. Phytochemistry 1974; 13: 65

Search in Google Scholar

15 Holland HL, Carter IM. Can. J. Chem. 1982; 60: 2420

Search in Google Scholar

16 Holland HL, Pöpperl H, Ninniss RW, Chenchaiah PC. Can. J. Chem. 1985; 63: 1118

Search in Google Scholar

17 Holland HL, Allen LJ, Chernishenko MJ, Diez M, Kohl A, Ozog J, Gu J.-X. J. Mol. Catal. B: Enzym. 1997; 3: 311

Search in Google Scholar

18 Holland HL, Rand CG, Viski P, Brown FM. Can. J. Chem. 1991; 69: 1989

Search in Google Scholar

19 Auret BJ, Boyd DR, Cassidy ES, Turley F, Drake SF, Mason SF. J. Chem. Soc., Chem. Commun. 1983; 282

20 Auret BJ, Boyd DR, Dunlop R. J. Chem. Soc., Perkin Trans. 1 1988; 2827

21 Holland HL, Brown FM, Larsen BG. Bioorg. Med. Chem. 1994; 2: 647

PubMed Search in Google Scholar

22 Holland HL, Bornmann MJ, Lakshmaiah G. J. Mol. Catal. B: Enzym. 1996; 1: 97

Search in Google Scholar

23 Holland HL, Brown FM, Larsen BG. Tetrahedron: Asymmetry 1994; 5: 1241

Search in Google Scholar

24 Holland HL, Brown FM, Larsen BG. Tetrahedron: Asymmetry 1995; 6: 1561

Search in Google Scholar

25 Holland HL, Brown FM, Kerridge A, Turner CD. J. Mol. Catal. B: Enzym. 1999; 6: 463

Search in Google Scholar

26 Holland HL, Turner CD, Andreana PR, Nguyen D. Can. J. Chem. 1999; 77: 463

Search in Google Scholar

27 Holland HL, Brown FM, Larsen BG, Zabic M. Tetrahedron: Asymmetry 1995; 6: 1569

Search in Google Scholar

28 Holland HL, Gu J.-X, Orallo F, Camiña M, Fabeiro P, Willetts AJ. Pharm. Res. 1999; 16: 281

PubMed Search in Google Scholar

29 Harris RZ, Newmyer SL, Ortiz de Montellano PR. J. Biol. Chem. 1993; 268: 1637

PubMed Search in Google Scholar

30 Ozaki S.-i, Ortiz de Montellano PR. J. Am. Chem. Soc. 1994; 116: 4487

Search in Google Scholar

31 Ozaki S.-i, Ortiz de Montellano PR. J. Am. Chem. Soc. 1995; 117: 7056

Search in Google Scholar

32 Adam W, Mock-Knoblauch C, Saha-Möller CR. J. Org. Chem. 1999; 64: 4834

PubMed Search in Google Scholar

33 Sangar S, Pal M, Moon LS, Jolly RS. Bioresour. Technol. 2012; 115: 102

PubMed Search in Google Scholar

34 Hofrichter M, Ullrich R. Appl. Microbiol. Biotechnol. 2006; 71: 276

PubMed Search in Google Scholar

35 Colonna S, Gaggero N, Manfredi A, Casella L, Gullotti M. J. Chem. Soc., Chem. Commun. 1988; 1451

36 Colonna S, Gaggero N, Manfredi A, Casella L, Gullotti M, Carrea G, Pasta P. Biochemistry 1990; 29: 10465

Search in Google Scholar

37 Colonna S, Gaggero N, Casella L, Carrea G, Pasta P. Tetrahedron: Asymmetry 1992; 3: 95

Search in Google Scholar

38 Fu H, Kondo H, Ichikawa Y, Look GC, Wong C.-H. J. Org. Chem. 1992; 57: 7265

Search in Google Scholar

39 Pasta P, Carrea G, Colonna S, Gaggero N. Biochim. Biophys. Acta, Protein Struct. Mol. Enzymol. 1994; 1209: 203

PubMed Search in Google Scholar

40 Allenmark SG, Andersson MA. Tetrahedron: Asymmetry 1996; 7: 1089

Search in Google Scholar

41 Allenmark SG, Andersson MA. Chirality 1998; 10: 246

Search in Google Scholar

42 van Deurzen MPJ, Remkes IJ, van Rantwijk F, Sheldon RA. J. Mol. Catal. A: Chem. 1997; 117: 329

Search in Google Scholar

43 van de Velde F, van Rantwijk F, Sheldon RA. J. Mol. Catal. B: Enzym. 1999; 6: 453

Search in Google Scholar

44 Pasta P, Carrea G, Gaggero N, Monzani E, Colonna S. Biotechnol. Bioeng. 1999; 62: 489

PubMed Search in Google Scholar

45 Conesa A, van de Velde F, van Rantwijk F, Sheldon RA, van den Hondel CAMJJ, Punt PJ. J. Biol. Chem. 2001; 276: 17635

PubMed Search in Google Scholar

46 Vargas RR, Bechara EJH, Marzorati L, Wladislaw B. Tetrahedron: Asymmetry 1999; 10: 3219

Search in Google Scholar

47 Holland HL, Brown FM, Johnson DV, Kerridge A, Mayne B, Turner CD, Vliet AJ. J. Mol. Catal. B: Enzym. 2002; 17: 249

Search in Google Scholar

48 Holland HL, Brown FM, Lozada D, Mayne B, Szerminski WR, van Vliet AJ. Can. J. Chem. 2002; 80: 633

Search in Google Scholar

49 ten Brink HB, Schoemaker HE, Wever R. Eur. J. Biochem. 2001; 268: 132

PubMed Search in Google Scholar

50 Andersson M, Willetts A, Allenmark S. J. Org. Chem. 1997; 62: 8455

PubMed Search in Google Scholar

51 Andersson MA, Allenmark SG. Tetrahedron 1998; 54: 15293

Search in Google Scholar

52 ten Brink HB, Tuynman A, Dekker HL, Hemrika W, Izumi Y, Oshiro T, Schoemaker HE, Wever R. Inorg. Chem. 1998; 38: 6780

Search in Google Scholar

53 ten Brink HB, Holland HL, Schoemaker HE, van Lingen H, Wever R. Tetrahedron: Asymmetry 1999; 10: 4563

Search in Google Scholar

54 van de Velde F, Konemann L, van Rantwijk F, Sheldon RA. Chem. Commun. (Cambridge) 1998; 1891

55 Cytochrome P450: Structure, Mechanism, and Biochemistry. Ortiz de Montellano PR. Kluwer Academic; New York 2005

Crossref Search in Google Scholar

56 Grogan G. Curr. Opin. Chem. Biol. 2011; 15: 241

PubMed Search in Google Scholar

57 Fasan R. ACS Catal. 2012; 2: 647

Crossref Search in Google Scholar

58 Urlacher VB, Girhard M. Trends Biotechnol. 2012; 30: 26

PubMed Search in Google Scholar

59 Waxman DJ, Light DR, Walsh C. Biochemistry 1982; 21: 2499

Search in Google Scholar

60 Kashiyama E, Yokoi T, Odomi M, Funae Y, Inoue K, Kamataki T. Drug Metab. Dispos. 1997; 25: 716

PubMed Search in Google Scholar

61 Äbelö A, Andersson TB, Antonsson M, Knuts Naudot A, Skånberg I, Weidof L. Drug Metab. Dispos. 2000; 28: 966

PubMed Search in Google Scholar

62 Moroni P, Buronfosse T, Longin-Sauvageon C, Delatour P, Benoit E. Drug Metab. Dispos. 1995; 23: 160

PubMed Search in Google Scholar

63 Fruetel J, Chang Y.-T, Collins J, Loew G, Ortiz de Montellano PR. J. Am. Chem. Soc. 1994; 116: 11643

Search in Google Scholar

64 Ohta H, Okamoto Y, Tsuchihashi G. Chem. Lett. 1984; 13: 205

Search in Google Scholar

65 Holland HL, Brown FM, Kerridge A, Pienkos P, Arensdor J. J. Mol. Catal. B: Enzym. 2003; 22: 219

Search in Google Scholar

66 Adam W, Heckel F, Saha-Möller CR, Taupp M, Meyer J.-M, Schreier P. Appl. Environ. Microbiol. 2005; 71: 2199

PubMed Search in Google Scholar

67 Li A.-T, Zhang J.-D, Xu J.-H, Lu W.-Y, Lin G.-Q. Appl. Environ. Microbiol. 2009; 75: 551

PubMed Search in Google Scholar

68 Zhang J.-D, Li A.-T, Yang Y, Xu J.-H. Appl. Microbiol. Biotechnol. 2010; 85: 615

PubMed Search in Google Scholar

69 Zhang J.-D, Li A.-T, Yu H.-L, Imanaka T, Xu J.-H. J. Ind. Microbiol. Biotechnol. 2011; 38: 633

PubMed Search in Google Scholar

70 van Berkel WJH, Kamerbeek NM, Fraaije MW. J. Biotechnol. 2006; 124: 670

PubMed Search in Google Scholar

71 Torres Pazmiño DE, Dudek HM, Fraaije MW. Curr. Opin. Chem. Biol. 2010; 14: 138

PubMed Search in Google Scholar

72 Leisch H, Morley K, Lau PCK. Chem. Rev. 2011; 111: 4165

PubMed Search in Google Scholar

73 Balke K, Kadow M, Mallin H, Bornscheuer UT. Org. Biomol. Chem. 2012; 10: 6249

PubMed Search in Google Scholar

74 Light DR, Waxman DJ, Walsh C. Biochemistry 1982; 21: 2490

Search in Google Scholar

75 Carrea G, Redigolo B, Riva S, Colonna S, Gaggero N, Battistel E, Bianchi D. Tetrahedron: Asymmetry 1992; 3: 1063

Search in Google Scholar

76 Secundo F, Carrea G, Dallavalle S, Franzosi G. Tetrahedron: Asymmetry 1993; 4: 1981

Search in Google Scholar

77 Colonna S, Gaggero N, Bertinotti A, Carrea G, Pasta P, Bernardi A. J. Chem. Soc., Chem. Commun. 1995; 1123

78 Colonna S, Gaggero N, Pasta P, Ottolina G. Chem. Commun. (Cambridge) 1996; 2303

79 Colonna S, Gaggero N, Carrea G, Pasta P. Chem. Commun. (Cambridge) 1997; 439

80 Malito E, Alfieri A, Fraaije MW, Mattevi A. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 13157

PubMed Search in Google Scholar

81 Mirza IA, Yachnin BJ, Wang S, Grosse S, Bergeron H, Imura A, Iwaki H, Hasegawa Y, Lau PCK, Berghuis AM. J. Am. Chem. Soc. 2009; 131: 8848

PubMed Search in Google Scholar

82 Chen G, Kayser MM, Mihovilovic MD, Mrstik ME, Martinez CA, Stewart JD. New J. Chem. 1999; 23: 827

Search in Google Scholar

83 Kayser MM, Zhao H, Chen G, Feicht A. ARKIVOC 2002; 47

84 Zambianchi F, Pasta P, Carrea G, Colonna S, Gaggero N, Woodley JM. Biotechnol. Bioeng. 2002; 78: 489

PubMed Search in Google Scholar

85 Reetz M, Daligault F, Brunner B, Hinrichs H, Deege A. Angew. Chem. Int. Ed. 2004; 43: 4078

PubMed Search in Google Scholar

86 Zhai X.-H, Ma Y.-H, Lai D.-Y, Zhou S, Chen Z.-M. J. Ind. Microbiol. Biotechnol. 2013; 40: 797

PubMed Search in Google Scholar

87 Bong YK, Clay MD, Collier SJ, Mijts B, Vogel M, Zhang X, Zhu J, Nazor J, Smith D, Song S. WO 2 011 071 982, 2011

PubMed

88 Fraaije MW, Wu J, Heuts DPHM, van Hellemond EW, Lutje Spelberg JH, Janssen DB. Appl. Microbiol. Biotechnol. 2005; 66: 393

PubMed Search in Google Scholar

89 de Gonzalo G, Pazmiño DET, Ottolina G, Fraaije MW, Carrea G. Tetrahedron: Asymmetry 2005; 16: 3077

Search in Google Scholar

90 Torres Pazmiño DE, Snajdrova R, Rial DV, Mihovilovic MD, Fraaije MW. Adv. Synth. Catal. 2007; 349: 1361

Search in Google Scholar

91 van Beek HL, de Gonzalo G, Fraaije MW. Chem. Commun. (Cambridge) 2012; 48: 3288

PubMed Search in Google Scholar

92 Kamerbeek NM, Olsthoorn AJJ, Fraaije MW, Janssen DB. Appl. Environ. Microbiol. 2003; 69: 419

PubMed Search in Google Scholar

93 Rioz-Martínez A, de Gonzalo G, Torres Pazmiño DE, Fraaije MW, Gotor V. Eur. J. Org. Chem. 2010; 2409

94 Jensen CN, Cartwright J, Ward J, Hart S, Turkenburg JP, Ali ST, Allen MJ, Grogan G. ChemBioChem 2012; 13: 872

PubMed Search in Google Scholar

95 Riebel A, de Gonzalo G, Fraaije MW. J. Mol. Catal. B: Enzym. 2013; 88: 20

Search in Google Scholar

96 Yeung CK, Rettie AE, Cytochrome P450 Protocols. Phillips IR, Shephard EA. Humana Press; Clifton, NJ 2005: 163

Crossref Search in Google Scholar

97 Hamman MA, Haehner-Daniels BD, Wrighton SA, Rettie AE, Hall SD. Biochem. Pharmacol. 2000; 60: 7

PubMed Search in Google Scholar

98 Cashman JR, Proudfoot J, Ho YK, Chin MS, Olsen LD. J. Am. Chem. Soc. 1989; 111: 4844

Search in Google Scholar

99 Cashman JR, Park SB, Yang ZC, Washington CB, Gomez DY, Giacomini KM, Brett CM. Drug Metab. Dispos. 1993; 21: 587

PubMed Search in Google Scholar

100 Rioz-Martínez A, de Gonzalo G, Torres Pazmiño DE, Fraaije MW, Gotor V. Eur. J. Org. Chem. 2010; 2409

101 Friemann R, Lee K, Brown EN, Gibson DT, Eklund H, Ramaswamy S. Acta Crystallogr., Sect. D 2009; 65: 24

PubMed Search in Google Scholar

102 Allen CCR, Boyd DR, Dalton H, Sharma ND, Haughey SA, McMordie RAS, McMurray BT, Sheldrake GN, Sproule K. J. Chem. Soc., Chem. Commun. 1995; 119

103 Lee K, Brand JM, Gibson DT. Biochem. Biophys. Res. Commun. 1995; 212: 9

PubMed Search in Google Scholar

104 Kerridge A, Willetts A, Holland H. J. Mol. Catal. B: Enzym. 1999; 6: 59

Search in Google Scholar

105 Boyd DR, Sharma ND, Byrne BE, Haughey SA, Kennedy MA, Allen CCR. Org. Biomol. Chem. 2004; 2: 2530

PubMed Search in Google Scholar

106 Boyd DR, Sharma ND, Haughey SA, Kennedy MA, Malone JF, Shepherd SD, Allen CCR, Dalton H. Tetrahedron 2004; 60: 549

Search in Google Scholar

107 Pievo R, Gullotti M, Monzani E, Casella L. Biochemistry 2008; 47: 3493

Search in Google Scholar

108 Feingersch R, Shainsky J, Wood TK, Fishman A. Appl. Environ. Microbiol. 2008; 74: 1555

PubMed Search in Google Scholar

109 Brouk M, Derry N.-L, Shainsky J, Ben-Barak Zelas Z, Boyko Y, Dabush K, Fishman A. J. Mol. Catal. B: Enzym. 2010; 66: 72

Search in Google Scholar

110 Hibi M, Kawashima T, Yajima H, Smirnov SV, Kodera T, Sugiyama M, Shimizu S, Yokozeki K, Ogawa J. Tetrahedron: Asymmetry 2013; 24: 990

Search in Google Scholar

111 Sugimoto T, Kokubo T, Miyazaki J, Tanimoto S, Okano M. Bioorg. Chem. 1981; 10: 311

Search in Google Scholar

112 Colonna S, Banfi S, Fontana F, Sommaruga M. J. Org. Chem. 1985; 50: 769

Search in Google Scholar

113 Colonna S, Banfi S, Annunziata R, Casella L. J. Org. Chem. 1986; 51: 891

Search in Google Scholar

114 Colonna S, Gaggero N. Tetrahedron Lett. 1989; 30: 6233

Search in Google Scholar

115 Colonna S, Gaggero N, Leone M. Tetrahedron 1991; 47: 8385

Search in Google Scholar

116 Ozaki S.-i, Matsui T, Watanabe Y. J. Am. Chem. Soc. 1996; 118: 9784

Search in Google Scholar

117 Ozaki S.-i, Yang H.-J, Matsui T, Goto Y, Watanabe Y. Tetrahedron: Asymmetry 1999; 10: 183

Search in Google Scholar

118 Ricoux R, Allard M, Dubuc R, Dupont C, Marechal JD, Mahy JP. Org. Biomol. Chem. 2009; 7: 3208

PubMed Search in Google Scholar

119 Rousselot-Pailley P, Bochot C, Marchi-Delapierre C, Jorge-Robin A, Martin L, Fontecilla-Camps JC, Cavazza C, Ménage S. ChemBioChem 2009; 10: 545

PubMed Search in Google Scholar

120 Pordea A, Creus M, Panek J, Duboc C, Mathis DB, Novic M, Ward TR. J. Am. Chem. Soc. 2008; 130: 8085

PubMed Search in Google Scholar