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Faber, K. et al.: 2015 Science of Synthesis, 1: Biocatalysis in Organic Synthesis 1 DOI: 10.1055/sos-SD-214-00071
Biocatalysis in Organic Synthesis 1

1.2 Strategies and Methods in Biocatalysis

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

Authors: Asano, Y.; Babich, L.; Bertau, M.; Cobucci-Ponzano, B.; Díaz-Rodríguez, A.; Engel, U.; Faber, K.; Flitsch, S. L.; Glueck, S. M.; Gotor-Fernández, V.; Green, A. P.; Hall, M.; Hartog, A. F.; Hepworth, L. J.; Hollmann, F.; Jeromin, G. E.; Lauchli, R.; Lavandera, I.; Liese, A.; Martínková, L.; Moracci, M.; Pesci, L.; Rodríguez-Mata, M.; Rozzell, D.; Rudat, J.; Schmidberger, J. W.; Servi, S.; Slomka, C.; Syldatk, C.; Tasnádi, G.; Tessaro, D.; Veselá, A. B.; Voglmeir, J.; Wever, R.

Title: Biocatalysis in Organic Synthesis 1

Print ISBN: 9783131741318; Online ISBN: 9783131975218; Book DOI: 10.1055/b-003-125815

1st edition © 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

The use of biocatalysts in organic synthesis and, particularly, in the preparation of optically pure chemicals offers major advantages in terms of selectivity, efficiency, safety, and sustainability. Thus, research groups are becoming more interested in biocatalysis as a tool for challenging synthetic routes. Herein we focus on the different strategies and methods that chemists have designed in order to obtain enantioenriched compounds starting from prochiral or racemic derivatives using enzymes or whole cells as catalysts. In the first part of the chapter, enzymatic desymmetrizations are presented, followed by other established systems dealing with racemates to attain a single or two enantiopure derivatives in the same reaction vessel. Then, the preparation of optically pure compounds in excellent yields and enantiomeric excesses by means of deracemization techniques is discussed. Finally, some recent examples where the combination of enzymes with other (bio)catalysts has provided high-added-value targets are shown.

Key words

desymmetrizations - kinetic resolutions - parallel kinetic resolutions - (cyclic) deracemizations - enantioconvergent processes - dynamic kinetic resolutions - dynamic kinetic asymmetric transformations - concurrent catalysis - cascade reactions - tandem reactions - one-pot reactions - multistep catalysis
 
  • 1 Wenda S, Illner S, Mell A, Kragl U. Green Chem. 2011; 13: 3007
  • 2 Bornscheuer UT, Huisman GW, Kazlauskas RJ, Lutz S, Moore JC, Robins K. Nature (London) 2012; 485: 185
  • 3 Woodley JM, Breuer M, Mink D. Chem. Eng. Res. Des. 2013; 91: 2029
  • 5 Behrens GA, Hummel A, Padhi SK, Schätzle S, Bornscheuer UT. Adv. Synth. Catal. 2011; 353: 2191
  • 6 Davids T, Schmidt M, Boettcher D, Bornscheuer UT. Curr. Opin. Chem. Biol. 2013; 17: 215
    PubMed
  • 7 Woodley JM. Curr. Opin. Chem. Biol. 2013; 17: 310
  • 8 Nestl BM, Nebel BA, Hauer B. Curr. Opin. Chem. Biol. 2011; 15: 187
  • 9 Muñoz Solano D, Hoyos P, Hernáiz MJ, Alcántara AR, Sánchez-Montero JM. Bioresour. Technol. 2012; 115: 196
    PubMed
  • 10 Bjerre J, Rousseau C, Marinescu L, Bols M. Appl. Microbiol. Biotechnol. 2008; 81: 1
  • 11 Breslow R. J. Biol. Chem. 2009; 284: 1337
    PubMed
  • 12 Asymmetric Organic Synthesis with Enzymes. Gotor V, Alfonso I, García-Urdiales E. Wiley-VCH; Weinheim, Germany 2008
    CrossrefGoogle Scholar
  • 13 Moss GP. Pure Appl. Chem. 1996; 68: 2193
  • 14 Fersht A. Structure and Mechanism in Protein Science. W. H. Freeman; New York 1999
    Google Scholar
  • 15 Jacobsen EE, Anthonsen T, Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions Fessner W.-D, Anthonsen T. Wiley-VCH Weinheim, Germany 2009; 96
  • 16 García-Urdiales E, Alfonso I, Gotor V. Chem. Rev. 2011; 111: PR110
    PubMed
  • 17 García-Urdiales E, Lavandera I, Gotor V, Enzyme Catalysis in Organic Synthesis Drauz K, Gröger H, May O. Wiley-VCH Weinheim, Germany 2012; 43
    Crossref
  • 18 Cahn RS, Ingold CK, Prelog V. Angew. Chem. 1966; 78: 413 Angew. Chem. Int. Ed. Engl. 1966; 5: 385
  • 19 Chen C.-S, Fujimoto Y, Girdaukas G, Sih CJ. J. Am. Chem. Soc. 1982; 104: 7294
  • 20 Straathof AJJ, Jongejan JA. Enzyme Microb. Technol. 1997; 21: 559
  • 21 biocatalysis.uni-graz.at/enantio/cgi-bin/enantio.pl (accessed April 2014).
  • 22 Rakels JLL, Straathof AJJ, Hiejnen JJ. Enzyme Microb. Technol. 1993; 15: 1051
    PubMed
  • 23 Chen C.-S, Wu S.-H, Girdaukas G, Sih CJ. J. Am. Chem. Soc. 1987; 109: 2812
  • 24 Caron G, Kazlauskas RJ. Tetrahedron: Asymmetry 1993; 4: 1995
  • 25 Xie Y.-C, Liu H.-Z, Chen J.-Y. Biotechnol. Lett. 1998; 20: 455
  • 26 Dehli JR, Gotor V. Chem. Soc. Rev. 2002; 31: 365
    PubMed
  • 27 Henrot M, Richter MEA, Maddaluno J, Hertweck C, De Paolis M. Angew. Chem. 2012; 124: 9725 Angew. Chem. Int. Ed. 2012; 51: 9587
    PubMed
  • 28 Berezina N, Kozma E, Furstoss R, Alphand V. Adv. Synth. Catal. 2007; 349: 2049
  • 29 Fink MJ, Fischer TC, Rudroff F, Dudek H, Fraaije MW, Mihovilovic MD. J. Mol. Catal. B: Enzym. 2011; 73: 9
  • 30 Martínez-Montero S, Fernández S, Sanghvi YS, Gotor V, Ferrero M. J. Org. Chem. 2010; 75: 6605
    PubMed
  • 31 Dehli JR, Gotor V. J. Org. Chem. 2002; 67: 1716
    PubMed
  • 32 Bianchi P, Roda G, Riva S, Danieli B, Zabelinskaja-Mackova A, Griengl H. Tetrahedron 2001; 57: 2213
  • 33 Dehli JR, Gotor V. ARKIVOC 2002; 196
  • 34 Faber K. Chem.–Eur. J. 2001; 7: 5005
  • 35 Gruber CC, Lavandera I, Faber K, Kroutil W. Adv. Synth. Catal. 2006; 348: 1789
  • 36 Voss CV, Gruber CC, Kroutil W. Synlett 2010; 991
  • 37 Rachwalski M, Vermue N, Rutjes FPJT. Chem. Soc. Rev. 2013; 42: 9268
    PubMed
  • 38 Soda K, Oikawa T, Yokoigawa K. J. Mol. Catal. B: Enzym. 2001; 11: 149
  • 39 Voss CV, Gruber CC, Faber K, Knaus T, Macheroux P, Kroutil W. J. Am. Chem. Soc. 2008; 130: 13969
    PubMed
  • 40 Kato D, Mitsuda S, Ohta H. J. Org. Chem. 2003; 68: 7234
    PubMed
  • 41 Shin G, Mathew S, Shon M, Kim B.-G, Yun H. Chem. Commun. (Cambridge) 2013; 49: 8629
    PubMed
  • 42 Köhler V, Wilson YM, Dürrenberger M, Ghislieri D, Churakova E, Quinto T, Knörr L, Häussinger D, Hollmann F, Turner NJ, Ward TR. Nat. Chem. 2013; 5: 93
    PubMed
  • 43 Turner NJ. Chem. Rev. 2011; 111: 4073
    PubMed
  • 44 Turner NJ, Enzyme Catalysis in Organic Synthesis Drauz K, Gröger H, May O. Wiley-VCH Weinheim, Germany 2012; 1535
    Crossref
  • 45 Kroutil W, Faber K. Tetrahedron: Asymmetry 1998; 9: 2901
  • 46 Strauss UT, Felfer U, Faber K. Tetrahedron: Asymmetry 1999; 10: 107
  • 47 Biade AE, Bourdillon C, Laval JM, Mairesse G, Moiroux J. J. Am. Chem. Soc. 1992; 114: 893
  • 48 Oikawa T, Mukoyama S, Soda K. Biotechnol. Bioeng. 2001; 73: 80
    PubMed
  • 49 Wallner SR, Pogorevc M, Trauthwein H, Faber K. Eng. Life Sci. 2004; 4: 512
  • 50 Kroutil W, Mischitz M, Faber K. J. Chem. Soc., Perkin Trans. 1 1997; 3629
  • 51 Pedragosa-Moreau S, Archelas A, Furstoss R. J. Org. Chem. 1993; 58: 5533
  • 52 Schober M, Toesch M, Knaus T, Strohmeier GA, van Loo B, Fuchs M, Hollfelder F, Macheroux P, Faber K. Angew. Chem. 2013; 125: 3359 Angew. Chem. Int. Ed. 2013; 52: 3277
    PubMed
  • 53 Takano S, Suzuki M, Ogasawara K. Tetrahedron: Asymmetry 1993; 4: 1043
  • 54 Lemke K, Ballschuh S, Kunath A, Theil F. Tetrahedron: Asymmetry 1997; 8: 2051
  • 55 Gadler P, Faber K. Trends Biotechnol. 2007; 25: 83
    PubMed
  • 56 Schober M, Knaus T, Toesch M, Macheroux P, Wagner U, Faber K. Adv. Synth. Catal. 2012; 354: 1737
  • 57 Szymański W, Westerbeek A, Janssen DB, Feringa BL. Angew. Chem. 2011; 123: 10900 Angew. Chem. Int. Ed. 2011; 50: 10712
    PubMed
  • 58 Lee JH, Han K, Kim M.-J, Park J. Eur. J. Org. Chem. 2010; 999
  • 59 Pellissier H. Tetrahedron 2011; 67: 3769
  • 60 Kim Y, Park J, Kim M.-J. ChemCatChem 2011; 3: 271
  • 61 Hussain I, Bäckvall J.-E, Enzyme Catalysis in Organic Synthesis Drauz K, Gröger H, May O. Wiley-VCH Weinheim, Germany 2012; 1777
    Crossref
  • 62 Tan DS, Günter MM, Drueckhammer DG. J. Am. Chem. Soc. 1995; 117: 9093
  • 63 Ebbers EJ, Ariaans GJA, Houbiers JPM, Bruggink A, Zwanenburg B. Tetrahedron 1997; 53: 9417
  • 64 Asano Y, Hölsch K, Enzyme Catalysis in Organic Synthesis Drauz K, Gröger H, May O. Wiley-VCH Weinheim, Germany 2012; 1607
    Crossref
  • 65 Schichl DA, Enthaler S, Holla W, Riermeier T, Kragl U, Beller M. Eur. J. Org. Chem. 2008; 3506
  • 66 El Blidi L, Nechab M, Vanthuyne N, Gastaldi S, Bertrand MP, Gil G. J. Org. Chem. 2009; 74: 2901
    PubMed
  • 67 Vongvilai P, Larsson R, Ramström O. Adv. Synth. Catal. 2008; 350: 448
  • 68 Vongvilai P, Ramström O. J. Am. Chem. Soc. 2009; 131: 14419
    PubMed
  • 69 van der Deen H, Cuiper AD, Hof RP, van Oeveren A, Feringa BL, Kellogg RM. J. Am. Chem. Soc. 1996; 118: 3801
  • 70 Thuring JWJF, Klunder AJH, Nefkens GHL, Wegman MA, Zwanenburg B. Tetrahedron Lett. 1996; 37: 4759
  • 71 Sharfuddin M, Narumi A, Iwai Y, Miyazawa K, Yamada S, Kakuchi T, Kaga H. Tetrahedron: Asymmetry 2003; 14: 1581
  • 72 Lozano P, De Diego T, Mira C, Montague K, Vaultier M, Iborra JL. Green Chem. 2009; 11: 538
  • 73 Cuetos A, Rioz-Martínez A, Bisogno FR, Grischek B, Lavandera I, de Gonzalo G, Kroutil W, Gotor V. Adv. Synth. Catal. 2012; 354: 1749
  • 74 Rioz-Martínez A, Cuetos A, Rodríguez C, de Gonzalo G, Lavandera I, Fraaije MW, Gotor V. Angew. Chem. 2011; 123: 8537 Angew. Chem. Int. Ed. 2011; 50: 8387
    PubMed
  • 75 Cuetos A, Lavandera I, Gotor V. Chem. Commun. (Cambridge) 2013; 49: 10688
    PubMed
  • 76 Shvo Y, Czarkie D, Rahamim Y, Chodosh DF. J. Am. Chem. Soc. 1986; 108: 7400
  • 77 Trost BM, Bunt RC, Lemoine RC, Calkins TL. J. Am. Chem. Soc. 2000; 122: 5968
  • 78 Steinreiber J, Faber K, Griengl H. Chem.–Eur. J. 2008; 14: 8060
    PubMed
  • 79 Martín-Matute B, Edin M, Bäckvall J.-E. Chem.–Eur. J. 2006; 12: 6053
    PubMed
  • 80 Borén L, Leijondahl K, Bäckvall J.-E. Tetrahedron Lett. 2009; 50: 3237
  • 81 Krumlinde P, Bogár K, Bäckvall J.-E. Chem.–Eur. J. 2010; 16: 4031
    PubMed
  • 82 Steinreiber J, Schürmann M, Wolberg M, van Assema F, Reisinger C, Fesko K, Mink D, Griengl H. Angew. Chem. 2007; 119: 1648 Angew. Chem. Int. Ed. 2007; 46: 1624
    PubMed
  • 83 Steinreiber J, Schürmann M, van Assema F, Wolberg M, Fesko K, Reisinger C, Mink D, Griengl H. Adv. Synth. Catal. 2007; 349: 1379
  • 84 Enzyme Catalysis in Organic Synthesis. Drauz K, Gröger H, May O. Wiley-VCH; Weinheim, Germany 2012
    CrossrefGoogle Scholar
  • 85 Tietze LF, Brasche G, Gericke KM. Domino Reactions in Organic Synthesis. Wiley-VCH; Weinheim, Germany 2006
    CrossrefGoogle Scholar
  • 86 Bruggink A, Schoevaart R, Kieboom T. Org. Process Res. Dev. 2003; 7: 622
  • 87 Pellissier H. Tetrahedron 2013; 69: 7171
  • 88 Ricca E, Brucher B, Schrittwieser JH. Adv. Synth. Catal. 2011; 353: 2239
  • 89 Vaxelaire C, Winter P, Christmann M. Angew. Chem. 2011; 123: 3685 Angew. Chem. Int. Ed. 2011; 50: 3605
    PubMed
  • 90 Trost BM. Science (Washington, D. C.) 1991; 254: 1471
    PubMed
  • 91 Burns NZ, Baran PS, Hoffmann RW. Angew. Chem. 2009; 121: 2896 Angew. Chem. Int. Ed. 2009; 48: 2854
    PubMed
  • 92 Clarke PA, Santos S, Martin WHC. Green Chem. 2007; 9: 438
  • 93 Hayashi Y, Umemiya S. Angew. Chem. 2013; 125: 3435 Angew. Chem. Int. Ed. 2013; 52: 3450
    PubMed
  • 94 Green Chemistry: Designing Chemistry for the Environment. Anastas PT, Williamson TC. Oxford University Press; Oxford 1998
    Google Scholar
  • 95 Anastas P, Eghbali N. Chem. Soc. Rev. 2010; 39: 301
    PubMed
  • 96 Sheldon RA, Multi-Step Enzyme Catalysis: Biotransformations and Chemoenzymatic Synthesis García-Junceda E. Wiley-VCH Weinheim, Germany 2008; 109
    Crossref
  • 97 Lopez-Gallego F, Schmidt-Dannert C. Curr. Opin. Chem. Biol. 2010; 14: 174
    PubMed
  • 98 Schrittwieser JH, Sattler J, Resch V, Mutti FG, Kroutil W. Curr. Opin. Chem. Biol. 2011; 15: 249
    PubMed
  • 99 Bisogno FR, Lavandera I, Gotor V. Kirk-Othmer Encyclopedia of Chemical Technology Wiley Hoboken, NJ 2011; 1
  • 100 Oroz-Guinea I, García-Junceda E. Curr. Opin. Chem. Biol. 2013; 17: 236
    PubMed
  • 101 Hollmann F, Arends IWCE, Buehler K. ChemCatChem 2010; 2: 762
  • 102 Rodríguez C, Lavandera I, Gotor V. Curr. Org. Chem. 2012; 16: 2525
  • 103 Aksu S, Arends IWCE, Hollmann F. Adv. Synth. Catal. 2009; 351: 1211
  • 104 Ferrandi EE, Monti D, Patel I, Kittl R, Haltrich D, Riva S, Ludwig R. Adv. Synth. Catal. 2012; 354: 2821
  • 105 Könst P, Kara S, Kochius S, Holtmann D, Arends IWCE, Ludwig R, Hollmann F. ChemCatChem 2013; 5: 3027
  • 106 Voss CV, Gruber CC, Kroutil W. Angew. Chem. 2008; 120: 753 Angew. Chem. Int. Ed. 2008; 47: 741
    PubMed
  • 107 Gruber CC, Nestl BM, Gross J, Hildebrandt P, Bornscheuer UT, Faber K, Kroutil W. Chem.–Eur. J. 2007; 13: 8271
    PubMed
  • 108 Monti D, Ferrandi EE, Zanellato I, Hua L, Polentini F, Carrea G, Riva S. Adv. Synth. Catal. 2009; 351: 1303
  • 109 Simon RC, Richter N, Busto E, Kroutil W. ACS Catal. 2014; 4: 129
  • 110 Koszelewski D, Grischek B, Glueck SM, Kroutil W, Faber K. Chem.–Eur. J. 2011; 17: 378
    PubMed
  • 111 Koszelewski D, Pressnitz D, Clay D, Kroutil W. Org. Lett. 2009; 11: 4810
    PubMed
  • 112 Koszelewski D, Müller N, Schrittwieser JH, Faber K, Kroutil W. J. Mol. Catal. B: Enzym. 2010; 63: 39
  • 113 Fuchs M, Tauber K, Sattler J, Lechner H, Pfeffer J, Kroutil W, Faber K. RSC Adv. 2012; 2: 6262
  • 114 Sattler JH, Fuchs M, Tauber K, Mutti FG, Faber K, Pfeffer J, Haas T, Kroutil W. Angew. Chem. 2012; 124: 9290 Angew. Chem. Int. Ed. 2012; 51: 9156
    PubMed
  • 115 Simon RC, Grischek B, Zepeck F, Steinreiber A, Belaj F, Kroutil W. Angew. Chem. 2012; 124: 6817 Angew. Chem. Int. Ed. 2012; 51: 6713
    PubMed
  • 116 Schrittwieser JH, Lavandera I, Seisser B, Mautner B, Lutje Spelberg JH, Kroutil W. Tetrahedron: Asymmetry 2009; 20: 483
  • 117 Schrittwieser JH, Lavandera I, Seisser B, Mautner B, Kroutil W. Eur. J. Org. Chem. 2009; 2293
  • 118 Ma SK, Gruber J, Davis C, Newman L, Gray D, Wang A, Grate J, Huisman GW, Sheldon RA. Green Chem. 2010; 12: 81
  • 119 Szymanski W, Postema CP, Tarabiono C, Berthiol F, Campbell-Verduyn L, de Wildeman S, de Vries JG, Feringa BL, Janssen DB. Adv. Synth. Catal. 2010; 352: 2111
  • 120 Wu S, Chen Y, Xu Y, Li A, Xu Q, Glieder A, Li Z. ACS Catal. 2014; 4: 409
  • 121 Di Gennaro P, Kazandjian LV, Mezzetti F, Sello G. Arch. Microbiol. 2013; 195: 269
    PubMed
  • 122 Schrewe M, Ladkau N, Bühler B, Schmid A. Adv. Synth. Catal. 2013; 355: 1693
  • 123 Peters RJRW, Marguet M, Marais S, Fraaije MW, van Hest JCM, Lecommandoux S. Angew. Chem. 2014; 126: 150 Angew. Chem. Int. Ed. 2014; 53: 146
  • 124 Denard CA, Hartwig JF, Zhao H. ACS Catal. 2013; 3: 2856
  • 125 Hollmann F, Lin P.-C, Witholt B, Schmid A. J. Am. Chem. Soc. 2003; 125: 8209
    PubMed
  • 126 Quinto T, Köhler V, Ward TR. Top. Catal. 2014; 57: 321
  • 127 Hildebrand F, Lütz S. Chem.–Eur. J. 2009; 15: 4998
    PubMed
  • 128 Poizat M, Arends IWCE, Hollmann F. J. Mol. Catal. B: Enzym. 2010; 63: 149
  • 129 Lutz J, Hollmann F, Ho TV, Schnyder A, Fish RH, Schmid A. J. Organomet. Chem. 2004; 689: 4783
  • 130 Höllrigl V, Otto K, Schmid A. Adv. Synth. Catal. 2007; 349: 1337
  • 131 Hildebrand F, Lütz S. Tetrahedron: Asymmetry 2007; 18: 1187
  • 132 Burda E, Hummel W, Gröger H. Angew. Chem. 2008; 120: 9693 Angew. Chem. Int. Ed. 2008; 47: 9551
    PubMed
  • 133 Gauchot V, Kroutil W, Schmitzer AR. Chem.–Eur. J. 2010; 16: 6748
    PubMed
  • 134 Kanbak-Aksu S, Hasan MN, Hagen WR, Hollmann F, Sordi D, Sheldon RA, Arends IWCE. Chem. Commun. (Cambridge) 2012; 48: 5745
    PubMed
  • 135 Filice M, Marciello M, del Puerto Morales M, Palomo JM. Chem. Commun. (Cambridge) 2013; 49: 6876
    PubMed
  • 136 Tenbrink K, Seßler M, Schatz J, Gröger H. Adv. Synth. Catal. 2011; 353: 2363
  • 137 Denard CA, Huang H, Bartlett MJ, Lu L, Tan Y, Zhao H, Hartwig JF. Angew. Chem. 2014; 126: 475 Angew. Chem. Int. Ed. 2014; 53: 465
    PubMed
  • 138 Wang ZJ, Clary KN, Bergman RG, Raymond KN, Toste FD. Nat. Chem. 2013; 5: 100
    PubMed
  • 139 Hanefeld U, Gardossi L, Magner E. Chem. Soc. Rev. 2009; 38: 453
    PubMed
  • 140 Engström K, Johnston EV, Verho O, Gustafson KPJ, Shakeri M, Tai C.-W, Bäckvall J.-E. Angew. Chem. 2013; 125: 14256 Angew. Chem. Int. Ed. 2013; 52: 14006
    PubMed
  • 141 Ward TR. Acc. Chem. Res. 2011; 44: 47
    PubMed
  • 142 Hyster TK, Knörr L, Ward TR, Rovis T. Science (Washington, D. C.) 2012; 338: 500
    PubMed
  • 143 Foulkes JM, Malone KJ, Coker VS, Turner NJ, Lloyd JR. ACS Catal. 2011; 1: 1589
  • 144 Baer K, Kraußer M, Burda E, Hummel W, Berkessel A, Gröger H. Angew. Chem. 2009; 121: 9519 Angew. Chem. Int. Ed. 2009; 48: 9355
    PubMed
  • 145 Sonoike S, Itakura T, Kitamura M, Aoki S. Chem.–Asian J. 2012; 7: 64
    PubMed