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Faber, K. et al.: 2015 Science of Synthesis: Biocatalysis in Organic Synthesis DOI: 10.1055/sos-SD-215-00136
Biocatalysis in Organic Synthesis 2

2.3.2 Addition of Water to C=C Bonds

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

Authors: Au, S. K.; Bartsch, S.; Beecher, D.; Boffi, A.; Bommarius, A. S.; Bonamore, A.; Brown, G.; Busto, E.; Clapés, P.; Faber, K.; Fischereder, E.-M.; France, S. P.; Fuchs, C. S.; Geertsema, E. M.; Glieder, A.; Gruber-Khadjawi, M.; Hall, M.; Hanefeld, U.; Hussain, S.; Ilari, A.; Janssen, D. B.; Kaluđerović, G. N.; Kroutil, W.; Lamm, A. S.; Leipold, F.; Lewin, R.; Li, A. T.; Li, Z.; Majerić Elenkov, M.; Micklefield, J.; Moody, T. S.; Mix, S.; Müller, M.; Poelarends, G. J.; Pohl, M.; Pressnitz, D.; Resch, V.; Richter, N.; Rosazza, J. P. N.; Schreckenbach, H. F.; Simon, R. C.; Steiner, K.; Szymański, W.; Thompson, M. L.; Turner, N. J.; Venkitasubramanian, P.; Vogel, A.; Wechsler, C.; Wessjohann, L. A.; Wohlgemuth, R.

Title: Biocatalysis in Organic Synthesis

Print ISBN: 9783131741615; Online ISBN: 9783131975317; Book DOI: 10.1055/b-003-125813

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

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

While chemists struggle to find efficient methods to perform the asymmetric addition of water, nature employs countless enzymes (called hydratases or hydro-lyases) to perform this reaction using substrates with both activated and nonactivated double bonds. However, compared to the vast number of hydratases involved in metabolic pathways in nature, only a few are described for their use in organic synthesis. Nevertheless, their potential in asymmetric catalysis has been recognized and some hydratases are used on a large scale in industrial processes. Since hydratases perform the addition of water, water is used as both a solvent and a reagent, opening up a very efficient and green route to both secondary and tertiary alcohols. This chapter focuses on hydratases that catalyze interesting reactions and are tested beyond their biochemical characterization.

Key words

acetylene hydratase - aconitase - carotenoid hydratases - citraconase - fumarase - hydratase - hydratase–tautomerase bifunctionality - hydro-lyase - kievitone hydratase - limonene hydratase - linalool dehydrogenase–isomerase - malease - oleate hydratase - phaseollidin hydratase - urocanase - water addition
 
  • 1 Davey PN, Earle MJ, Hamill JT, Katdare SP, Rooney DW, Seddon KR. Green Chem. 2010; 12: 628
  • 2 Wang S, Zhang Z, Chi C, Wu G, Ren J, Wang Z, Huang M, Jiang Y. React. Funct. Polym. 2008; 68: 424
  • 3 Wang X, Sui D, Huang M, Jiang Y. Polym. Adv. Technol. 2006; 17: 163
  • 4 Xue L, Jia B, Tang L, Ji XF, Huang MY, Jiang YY. Polym. Adv. Technol. 2004; 15: 346
  • 5 Hahn H.-D, Dämbkes G, Rupprich N, Bahl H, Frey GD. Ullmannʼs Encyclopedia of Industrial Chemistry. Wiley-VCH; Weinheim, Germany 2013
    Google Scholar
  • 6 Falbe J, Bahrmann H, Lipps W, Mayer D, Frey GD. Ullmannʼs Encyclopedia of Industrial Chemistry. Wiley-VCH; Weinheim, Germany 2013
    Google Scholar
  • 7 Sheldon RA, Arends IWCE, Hanefeld U. Green Chemistry and Catalysis. Wiley-VCH; Weinheim, Germany 2007
    Google Scholar
  • 8 Anderson VE, Ruszczycky MW, Harris ME. Chem. Rev. 2006; 106: 3236
  • 9 Zhang X, Houk KN. Acc. Chem. Res. 2005; 38: 379
  • 10 van der Werf MJ, van den Tweel WJJ, Kamphuis J, Hartmans S, de Bont JAM. Trends Biotechnol. 1994; 12: 95
  • 11 van Leeuwen BNM, van der Wulp AM, Duijnstee I, van Maris AJA, Straathof AJJ. Appl. Microbiol. Biotechnol. 2012; 93: 1377
  • 12 Tokoroyama T. Eur. J. Org. Chem. 2010; 2009
  • 13 Mohrig JR, Moerke KA, Cloutier DL, Lane BD, Person EC, Onasch TB. Science (Washington, D. C.) 1995; 269: 527
  • 14 Beinert H, Kennedy MC, Stout CD. Chem. Rev. 1996; 96: 2335
  • 15 Lauble H, Kennedy MC, Beinert H, Stout CD. J. Mol. Biol. 1994; 237: 437
  • 16 Rose IA, Weaver TM. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 3393
  • 17 Mohrig JR. Acc. Chem. Res. 2013; 46: 1407
  • 18 Holden HM, Benning MM, Haller T, Gerlt JA. Acc. Chem. Res. 2001; 34: 145
  • 19 Hanson KR, Rose IA. Acc. Chem. Res. 1975; 8: 1
  • 20 Gerlt JA, Gassman PG. J. Am. Chem. Soc. 1992; 114: 5928
  • 21 Bahnson BJ, Anderson VE, Petsko GA. Biochemistry 2002; 41: 2621
  • 22 Weaver T, Banaszak L. Biochemistry 1996; 35: 13955
  • 23 Weaver T. Acta Crystallogr., Sect. D 2005; 61: 1395
  • 24 Kourist R, Bornscheuer UT. Appl. Microbiol. Biotechnol. 2011; 91: 505
  • 25 Davis EN, Wallen LL, Goodwin JC, Rohwedder WK, Rhodes RA. Lipids 1969; 4: 356
  • 26 Niehaus Jr WG, Kisic A, Torkelson A, Bednarczyk DJ, Schroepfer Jr GJ. J. Biol. Chem. 1970; 245: 3790
  • 27 Wallen LL, Benedict RG, Jackson RW. Arch. Biochem. Biophys. 1962; 99: 249
  • 28 Kisic A, Miura Y, Schroepfer Jr GJ. Lipids 1971; 6: 541
  • 29 Bevers LE, Pinkse MWH, Verhaert PDEM, Hagen WR. J. Bacteriol. 2009; 191: 5010
  • 30 Joo Y.-C, Jeong K.-W, Yeom S.-J, Kim Y.-S, Kim Y, Oh D.-K. Biochimie 2012; 94: 907
  • 31 Gocho S, Tabogami N, Inagaki M, Kawabata C, Komai T. Biosci., Biotechnol., Biochem. 1995; 59: 1571
  • 32 Wanikawa A, Hosoi K, Takise I, Kato T. J. Inst. Brew. 2000; 106: 39
  • 33 Kim B.-N, Joo Y.-C, Kim Y.-S, Kim K.-R, Oh D.-K. Appl. Microbiol. Biotechnol. 2012; 95: 929
  • 34 Kim B.-N, Yeom S.-J, Oh D.-K. Biotechnol. Lett. 2011; 33: 993
  • 35 Joo Y.-C, Seo E.-S, Kim Y.-S, Kim K.-R, Park J.-B, Oh D.-K. J. Biotechnol. 2012; 158: 17
  • 36 Jeon E.-Y, Lee J.-H, Yang K.-M, Joo Y.-C, Oh D.-K, Park J.-B. Process Biochem. 2012; 47: 941
  • 37 Song J.-W, Jeon E.-Y, Song D.-H, Jang H.-Y, Bornscheuer UT, Oh D.-K, Park J.-B. Angew. Chem. 2013; 125: 2594 Angew. Chem. Int. Ed. 2013; 52: 2534
  • 38 Moise AR, Al-Babili S, Wurtzel ET. Chem. Rev. 2014; 114: 164
  • 39 Steiger S, Mazet A, Sandmann G. Arch. Biochem. Biophys. 2003; 414: 51
  • 40 Steiger S, Takaichi S, Sandmann G. J. Biotechnol. 2002; 97: 51
  • 41 Umeno D, Tobias AV, Arnold FH. Microbiol. Mol. Biol. Rev. 2005; 69: 51
  • 42 Sun Z, Shen S, Wang C, Wang H, Hu Y, Jiao J, Ma T, Tian B, Hua Y. Microbiology 2009; 155: 2775
  • 43 Hiseni A, Arends IWCE, Otten LG. Appl. Microbiol. Biotechnol. 2011; 91: 1029
  • 44 Brodkorb D, Gottschall M, Marmulla R, Lüddeke F, Harder J. J. Biol. Chem. 2010; 285: 30436
  • 45 Lüddeke F, Harder J. Z. Naturforsch., C 2011; 66: 409
  • 46 Cleveland TE, Smith DA. Physiol. Plant Pathol. 1983; 22: 129
  • 47 Li D, Chung K.-R, Smith DA, Schardl CL. Mol. Plant-Microbe Interact. 1995; 8: 388
  • 48 Turbek CS, Li D, Choi GH, Schardl CL, Smith DA. Phytochemistry 1990; 29: 2841
  • 49 Turbek CS, Smith DA, Schardl CL. FEMS Microbiol. Lett. 1992; 94: 187
  • 50 Pearlman PS, Chen C, Botes AL, Conradie AVE. US 2013 0 189 753, 2013 Chem. Abstr.. 2013 158 288625
    Google Scholar
  • 51 Marliere P. WO 2011 076 689, 2011 Chem. Abstr.. 2011 155 121541
    Google Scholar
  • 52 Cadwallader KR, Braddock RJ, Parish ME, Higgins DP. J. Food Sci. 1989; 54: 1241
  • 53 Maróstica Jr MR, Pastore GM. Food Chem. 2007; 101: 345
  • 54 Bicas JL, Barros FFC, Wagner R, Godoy HT, Pastore GM. J. Ind. Microbiol. Biotechnol. 2008; 35: 1061
  • 55 Bicas JL, de Quadros CP, Néri-Numa IA, Pastore GM. Food Chem. 2010; 120: 452
  • 56 Onken J, Berger RG. J. Biotechnol. 1999; 69: 163
  • 57 Rottava I, Toniazzo G, Cortina PF, Martello E, Grando CE, Lerin LA, Treichel H, Mossi AJ, de Oliveira D, Cansian RL, Antunes OAC, Oestreicher EG. LWT–Food Sci. Technol. 2010; 43: 1128
  • 58 Adams A, Demyttenaere JCR, De Kimpe N. Food Chem. 2003; 80: 525
  • 59 Badee AZM, Helmy SA, Morsy NFS. Food Chem. 2011; 126: 849
  • 60 Tan Q, Day DF. Appl. Microbiol. Biotechnol. 1998; 49: 96
  • 61 Cadwallader KR, Braddock RJ, Parish ME. J. Food Sci. 1992; 57: 241
  • 62 Savithiry N, Cheong T, Oriel P, Biotechnology for Fuels and Chemicals Davison BH, Wyman CE, Finkelstein M. Humana New York 1997; 63–65. 213
  • 63 Bicas JL, Fontanille P, Pastore GM, Larroche C. Process Biochem. 2010; 45: 481
  • 64 Pescheck M, Mirata MA, Brauer B, Krings U, Berger RG, Schrader J. J. Ind. Microbiol. Biotechnol. 2009; 36: 827
  • 65 Prieto SGA, Perea VJA, Ortiz LCC. Vitae 2011; 18: 163
  • 66 Rosner BM, Schink B. J. Bacteriol. 1995; 177: 5767
  • 67 Meckenstock RU, Krieger R, Ensign S, Kroneck PMH, Schink B. Eur. J. Biochem. 1999; 264: 176
  • 68 Seiffert GB, Ullmann GM, Messerschmidt A, Schink B, Kroneck PMH, Einsle O. Proc. Natl. Acad. Sci. U. S. A. 2007; 104: 3073
  • 69 Einsle O, Niessen H, Abt DJ, Seiffert G, Schink B, Huber R, Messerschmidt A, Kroneck PMH. Acta Crystallogr., Sect. F 2005; 61: 299
  • 70 ten Brink F, Schink B, Kroneck PMH. J. Bacteriol. 2011; 193: 1229
  • 71 Liao R.-Z, Thiel W. J. Chem. Theory Comput. 2012; 8: 3793
  • 72 de Bont JAM, Peck M. Arch. Microbiol. 1980; 127: 99
  • 73 Germon JC, Knowles R. Can. J. Microbiol. 1988; 34: 242
  • 74 Kanner D, Bartha R. J. Bacteriol. 1979; 139: 225
  • 75 Span I, Wang K, Wang W, Zhang Y, Bacher A, Eisenreich W, Li K, Schulz C, Oldfield E, Groll M. Nature Commun. 2012; 3: 1042
  • 76 Lamartiniere CA, Braymer HD, Larson AD. Arch. Biochem. Biophys. 1970; 141: 293
  • 77 Yumoto N, Tokushige M. Biochem. Biophys. Res. Commun. 1988; 153: 1236
  • 78 Flint DH, Allen RM. Chem. Rev. 1996; 96: 2315
  • 79 Woods SA, Schwartzbach SD, Guest JR. Biochim. Biophys. Acta, Protein Struct. Mol. Enzymol. 1988; 954: 14
  • 80 Ueda Y, Yumoto N, Tokushige M, Fukui K, Ohya-Nishiguchi H. J. Biochem. (Tokyo) 1991; 109: 728
  • 81 Flint DH. Arch. Biochem. Biophys. 1994; 311: 509
  • 82 Flint DH. Biochemistry 1993; 32: 799
  • 83 Flint DH, Emptage MH, Guest JR. Biochemistry 1992; 31: 10331
  • 84 Weaver T, Lees M, Zaitsev V, Zaitseva I, Duke E, Lindley P, McSweeny S, Svensson A, Keruchenko J, Keruchenko I, Gladilin K, Banaszak L. J. Mol. Biol. 1998; 280: 431
  • 85 Yang J, Wang Y, Woolridge EM, Arora V, Petsko GA, Kozarich JW, Ringe D. Biochemistry 2004; 43: 10424
  • 86 Weaver T, Lees M, Banaszak L. Protein Sci. 1997; 6: 834
  • 87 Bressler E, Pines O, Goldberg I, Braun S. Biotechnol. Prog. 2002; 18: 445
  • 88 Yamamoto K, Tosa T, Yamashita K, Chibata I. Eur. J. Appl. Microbiol. Biotechnol. 1976; 3: 169
  • 89 Takata I, Yamamoto K, Tosa T, Chibata I. Enzyme Microb. Technol. 1980; 2: 30
  • 90 Chibata I, Tosa T, Takata I. Trends Biotechnol. 1983; 1: 9
  • 91 Liese A, Seelbach K, Wandrey C. Industrial Biotransformations. Wiley-VCH; Weinheim, Germany 2006
    Google Scholar
  • 92 Tosa T, Shibatani T. Ann. N. Y. Acad. Sci. 1995; 750: 364
  • 93 Leuchtenberger W, Karrenbauer M, Plöcker U. Ann. N. Y. Acad. Sci. 1984; 434: 78
  • 94 Danneel H.-J, Geiger R. DE 4 430 010C1, 1996 Chem. Abstr.. 1996 124 201642
    Google Scholar
  • 95 Danneel H.-J, Geiger R. DE 4 424 664C1, 1995 Chem. Abstr.. 1995 123 337561
    Google Scholar
  • 96 Teipel JW, Hass GM, Hill RL. J. Biol. Chem. 1968; 243: 5684
  • 97 Findeis MA, Whitesides GM. J. Org. Chem. 1987; 52: 2838
  • 98 Sacks W, Jensen CO. J. Biol. Chem. 1951; 192: 231
  • 99 Dreyer J.-L. Eur. J. Biochem. 1985; 150: 145
  • 100 van der Werf MJ, van den Tweel WJJ, Hartmans S. Eur. J. Biochem. 1993; 217: 1011
  • 101 van der Werf MJ, van den Tweel WJJ, Hartmans S. Appl. Environ. Microbiol. 1992; 58: 2854
  • 102 van der Werf MJ, van den Tweel WJJ, Hartmans S. Appl. Environ. Microbiol. 1993; 59: 2823
  • 103 He B.-F, Nakajima-Kambe T, Ozawa T, Nakahara T. Process Biochem. 2000; 36: 407
  • 104 Ueda M, Yamada H, Asano Y. Appl. Microbiol. Biotechnol. 1994; 41: 215
  • 105 Michielsen MJF, Frielink C, Wijffels RH, Tramper J, Beeftink HH. J. Biotechnol. 2000; 79: 13
  • 106 Rao MRR, Subramanian SS, Rahatekar HI, Paranjape SV. Biochem. Biophys. Res. Commun. 1963; 12: 78
  • 107 Subramanian SS, Rao MRR. J. Biol. Chem. 1968; 243: 2367
  • 108 Brock M, Maerker C, Schütz A, Völker U, Buckel W. Eur. J. Biochem. 2002; 269: 6184
  • 109 Holz M, Förster A, Mauersberger S, Barth G. Appl. Microbiol. Biotechnol. 2009; 81: 1087
  • 110 Williams CH, Stillman TJ, Barynin VV, Sedelnikova SE, Tang Y, Green J, Guest JR, Artymiuk PJ. Nature Struct. Mol. Biol. 2002; 9: 447
  • 111 Serio AW, Sonenshein AL. J. Bacteriol. 2006; 188: 6406
  • 112 Kennedy MC, Mende-Mueller L, Blondin GA, Beinert H. Proc. Natl. Acad. Sci. U. S. A. 1992; 89: 11730
  • 113 Haile DJ, Rouault TA, Harford JB, Kennedy MC, Blondin GA, Beinert H, Klausner RD. Proc. Natl. Acad. Sci. U. S. A. 1992; 89: 11735
  • 114 Dickman SR, Cloutier AA. J. Biol. Chem. 1951; 188: 379
  • 115 Tyagi R, Eswaramoorthy S, Burley SK, Raushel FM, Swaminathan S. Biochemistry 2008; 47: 5608
  • 116 Gerlinger E, Hull WE, Rétey J. Tetrahedron 1983; 39: 3523
  • 117 Grueninger D, Treiber N, Ziegler MOP, Koetter JWA, Schulze M.-S, Schulz GE. Science (Washington, D. C.) 2008; 319: 206
  • 118 Kessler D, Rétey J, Schulz GE. J. Mol. Biol. 2004; 342: 183
  • 119 Rétey J. Arch. Biochem. Biophys. 1994; 314: 1
  • 120 Schubert C, Rétey J. Bioorg. Chem. 1994; 22: 368
  • 121 Schubert C, Zhao Y, Shin J.-H, Rétey J. Angew. Chem. 1994; 106: 1331 Angew. Chem. Int. Ed. Engl. 1994; 33: 1279
  • 122 Yamada EW, Jakoby WB. J. Am. Chem. Soc. 1958; 80: 2343
  • 123 Yamada EW, Jakoby WB. J. Biol. Chem. 1959; 234: 941
  • 124 Brecker L, Petschnigg J, Depiné N, Weber H, Ribbons DW. Eur. J. Biochem. 2003; 270: 1393
  • 125 Wang SC, Johnson WH, Whitman CP. J. Am. Chem. Soc. 2003; 125: 14282
  • 126 Poelarends GJ, Serrano H, Johnson WH, Hoffman DW, Whitman CP. J. Am. Chem. Soc. 2004; 126: 15658
  • 127 Almrud JJ, Poelarends GJ, Johnson WH, Serrano H, Hackert ML, Whitman CP. Biochemistry 2005; 44: 14818
  • 128 Poelarends GJ, Serrano H, Johnson WH, Whitman CP. Biochemistry 2005; 44: 9375
  • 129 de Jong RM, Brugman W, Poelarends GJ, Whitman CP, Dijkstra BW. J. Biol. Chem. 2004; 279: 11546
  • 130 Poelarends GJ, Veetil VP, Whitman CP. Cell. Mol. Life Sci. 2008; 65: 3606
  • 131 Poelarends GJ, Whitman CP. Bioorg. Chem. 2004; 32: 376
  • 132 Hiltunen JK, Qin Y.-M. Biochim. Biophys. Acta, Mol. Cell Biol. Lipids 2000; 1484: 117
  • 133 Agnihotri G, Liu H.-w. Bioorg. Med. Chem. 2003; 11: 9
  • 134 Bhaumik P, Koski MK, Glumoff T, Hiltunen JK, Wierenga RK. Curr. Opin. Struct. Biol. 2005; 15: 621
  • 135 Bell AF, Feng Y, Hofstein HA, Parikh S, Wu J, Rudolph MJ, Kisker C, Whitty A, Tonge PJ. Chem. Biol. 2002; 9: 1247
  • 136 Koski MK, Haapalainen AM, Hiltunen JK, Glumoff T. J. Biol. Chem. 2004; 279: 24666
  • 137 Koski MK, Haapalainen AM, Hiltunen JK, Glumoff T. J. Mol. Biol. 2005; 345: 1157
  • 138 Babbitt PC, Gerlt JA. J. Biol. Chem. 1997; 272: 30591
  • 139 Gerlt JA, Babbitt PC. Curr. Opin. Chem. Biol. 1998; 2: 607
  • 140 Müller-Newen G, Janssen U, Stoffel W. Eur. J. Biochem. 1995; 228: 68
  • 141 Hisano T, Tsuge T, Fukui T, Iwata T, Miki K, Doi Y. J. Biol. Chem. 2003; 278: 617
  • 142 Hasegawa J, Ogura M, Kanema H, Noda N, Kawaharada H, Watanabe K. J. Ferment. Technol. 1982; 60: 501
  • 143 Crosby J. Tetrahedron 1991; 47: 4789
  • 144 Kleber H.-P. FEMS Microbiol. Lett. 1997; 147: 1
  • 145 Jung H, Jung K, Kleber H.-P. Biochim. Biophys. Acta, Lipids Lipid Metab. 1989; 1003: 270
  • 146 Vandecasteele J.-P. Appl. Environ. Microbiol. 1980; 39: 327
  • 147 Zhou BN, Gopalan AS, VanMiddlesworth F, Shieh W.-R, Sih CJ. J. Am. Chem. Soc. 1983; 105: 5925
  • 148 Kulla H, Lehky P. EP 158 194, 1985 Chem. Abstr.. 1986 104 33037
    Google Scholar
  • 149 Seim H, Kleber H.-P. Appl. Microbiol. Biotechnol. 1988; 27: 538
  • 150 Engemann C, Elssner T, Kleber H.-P. Arch. Microbiol. 2001; 175: 353
  • 151 Alvarez-Vasquez F, Cánovas M, Iborra JL, Torres NV. Biotechnol. Bioeng. 2002; 80: 794
  • 152 Cánovas M, Maiquez JR, Obón JM, Iborra JL. Biotechnol. Bioeng. 2002; 77: 764
  • 153 Cánovas M, Torroglosa T, Iborra JL. Enzyme Microb. Technol. 2005; 37: 300
  • 154 Tian J, Wang Q, Zhang Z. Eur. Food Res. Technol. 2009; 229: 721
  • 155 Kulla HG. Chimia 1991; 45: 81
  • 156 Barghini P, Di Gioia D, Fava F, Ruzzi M. Microb. Cell Fact. 2007; 6: 13
  • 157 Negishi O, Sugiura K, Negishi Y. J. Agric. Food Chem. 2009; 57: 9956
  • 158 Li K, Frost JW. J. Am. Chem. Soc. 1998; 120: 10545
  • 159 Narbad A, Rhodes MJC, Gasson MJ, Walton NJ. WO 9 735 999A2, 1997 Chem. Abstr.. 1997 127 306674
    Google Scholar
  • 160 Calisti C, Ficca AG, Barghini P, Ruzzi M. Appl. Microbiol. Biotechnol. 2008; 80: 475
  • 161 Masai E, Harada K, Peng X, Kitayama H, Katayama Y, Fukuda M. Appl. Environ. Microbiol. 2002; 68: 4416
  • 162 Leonard PM, Brzozowski AM, Lebedev A, Marshall CM, Smith DJ, Verma CS, Walton NJ, Grogan G. Acta Crystallogr., Sect. D 2006; 62: 1494
  • 163 Leonard PM, Marshall CM, Dodson EJ, Walton NJ, Grogan G. Acta Crystallogr., Sect. D 2004; 60: 2343
  • 164 Bennett JP, Bertin L, Moulton B, Fairlamb IJS, Brzozowski AM, Walton NJ, Grogan G. Biochem. J. 2008; 414: 281
  • 165 Jin J, Oskam PC, Karmee SK, Straathof AJJ, Hanefeld U. Chem. Commun. (Cambridge) 2010; 46: 8588
  • 166 Jin J, Straathof AJJ, Pinkse MWH, Hanefeld U. Appl. Microbiol. Biotechnol. 2011; 89: 1831
  • 167 Dangel W, Tschech A, Fuchs G. Arch. Microbiol. 1988; 150: 358
  • 168 Dangel W, Tschech A, Fuchs G. Arch. Microbiol. 1989; 152: 273
  • 169 Resch V, Seidler C, Chen B.-S, Degeling I, Hanefeld U. Eur. J. Org. Chem. 2013; 7697
  • 170 Resch V, Jin J, Chen B.-S, Hanefeld U. AMB Express 2014; 4: 30
  • 171 Holland H, Gu J.-X. Biotechnol. Lett. 1998; 20: 1125
  • 172 Chen B.-S, Otten LG, Resch V, Muyzer G, Hanefeld U. Stand. Genomic Sci. 2013; 9: 175
  • 173 Müller M. Chem. Ing. Tech. 2013; 85: 795
  • 174 Wuensch C, Gross J, Steinkellner G, Gruber K, Glueck SM, Faber K. Angew. Chem. 2013; 125: 2349 Angew. Chem. Int. Ed. 2013; 52: 2293
  • 175 Wuensch C, Glueck SM, Gross J, Koszelewski D, Schober M, Faber K. Org. Lett. 2012; 14: 1974
  • 176 Bos J, García-Herraiz A, Roelfes G. Chem. Sci. 2013; 4: 3578
  • 177 Boersma AJ, Coquière D, Geerdink D, Rosati F, Feringa BL, Roelfes G. Nature Chem. 2010; 2: 991
  • 178 Boersma AJ, Megens RP, Feringa BL, Roelfes G. Chem. Soc. Rev. 2010; 39: 2083
  • 179 Oelerich J, Roelfes G. Chem. Sci. 2013; 4: 2013
  • 180 Megens RP, Roelfes G. Chem. Commun. (Cambridge) 2012; 48: 6366
  • 181 Rosati F, Roelfes G. ChemCatChem 2011; 3: 973