1.1.1 Historical Perspectives: Paving the Way for the Future

S. Servi; D. Tessaro; F. Hollmann

Abstract

This chapter describes the evolution of modern biocatalysis, focusing on the application of both whole-cell biocatalysts and isolated enzymes in organic synthesis. Milestones in this process are the application to β-lactam and amino acid chemistry, the preparation of chiral synthons as single enantiomers for the synthesis of pharmaceutical intermediates, the modification of carbohydrates and the synthesis of value-added products from lipids. The application of hydrolytic enzymes (lipases, proteases, esterases, and nitrile hydratases) has evolved in time toward more complex enzymatic systems such as oxidoreductases involving cofactor recycling or aminotransferases (transaminases) leading to the formation of chiral amines. The recently developed techniques of molecular biology and directed evolution toward the preparation of better enzymatic catalysts are dramatically improving the availability and efficiency of the enzymes and thus significantly increasing the role of biocatalysis in organic synthesis.

Schlüsselwörter

chiral synthons - whole-cell biocatalysis - hydrolytic enzymes - oxidoreductases - cofactor recycling - directed evolution - cascade biocatalysis

• 1 Neidleman SL, Biocatalysis Abramowicz DA. Van Nostrand Reinhold New York 1990; 1

• 2 Vasić-Rački Ð, Industrial Biotransformations Liese A, Seelbach K, Wandrey C. Wiley-VCH Weinheim, Germany 2006; 1

• 3 Borman S. Chem. Eng. News 1990; 68: 9

• 4 Stinson SC. Chem. Eng. News 1992; 70: 46

• 5 Testa B, Trager WF. Chirality 1990; 2: 129

• 6 Sheldon RA. Chirotechnology: Industrial Synthesis of Optically Active Compounds Marcel Dekker New York 1993; 1. 993

• 7 Collins AN, Sheldrake GN, Crosby J. Chirality in Industry: The Commercial Manufacture and Applications of Optically Active Compounds Wiley Chichester, U. K. 1992; 409

• 8 Sheldon RA. Drug Inf. J. 1990; 24: 129

• 9 Progress in Industrial Microbiology. Aida K, Chibata I, Nakayama K, Takinami K, Yamada H. Elsevier; Amsterdam 1986. 24.

• 10 Olivieri R, Fascetti E, Angelini L, Degen L. Biotechnol. Bioeng. 1981; 23: 2173

• 11 Giordano C, Castaldi G, Cavicchioli S, Villa M. Tetrahedron 1989; 45: 4243

• 12 Battistel E, Bianchi D, Cesti P, Pina C. Biotechnol. Bioeng. 1991; 38: 659

• 13 Mutsaers JHGM, Kooreman HJ. Recl. Trav. Chim. Pays-Bas 1991; 110: 185

• 14 Chan A. CHEMTECH 1993; 23: 46

• 15 Applications of Biochemical Systems in Organic Chemistry. Jones JB, Sih CJ, Perlman D. Wiley; New York 1976

• 16 Enzymes in Organic Synthesis. Porter R, Clark S. Pitman; London 1985

• 17 Biocatalysts in Organic Synthesis. Tramper J, van der Plas HC, Linko P. Elsevier; Amsterdam 1985

• 18 Enzymes as Catalysts in Organic Synthesis. Schneider MP. Reidel; Dordrecht, The Netherlands 1986

• 19 Bioorganic Chemistry in Healthcare and Technology. Pandit U, Alderweirelt F. Plenum; New York 1991

• 20 Microbial Reagents in Organic Synthesis Servi S. Springer Berlin 1992;

• 21 Reetz MT. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 5716

• 22 Reetz MT. Tetrahedron 2002; 58: 6595

• 23 Reetz MT, Rentzsch M, Pletsch A, Maywald M, Maiwald P, Peyralans JJ.-P, Maichele A, Fu Y, Jiao N, Hollmann F, Mondière R, Taglieber A. Tetrahedron 2007; 63: 6404

• 24 Reetz MT. J. Am. Chem. Soc. 2013; 135: 12480

• 25 Reetz MT. Angew. Chem. Int. Ed. 2011; 50: 138

• 26 Reetz MT. J. Org. Chem. 2009; 74: 5767

• 27 Reetz MT, Wang L.-W, Bocola M. Angew. Chem. Int. Ed. 2006; 45: 1236

• 28 Bornscheuer UT, Huisman GW, Kazlauskas RJ, Lutz S, Moore JC, Robins K. Nature (London) 2012; 485: 185

• 29 Fox RJ, Huisman GW. Trends Biotechnol. 2008; 26: 132

• 30 Fox RJ, Davis SC, Mundorff EC, Newman LM, Gavrilovic V, Ma SK, Chung LM, Ching C, Tam S, Muley S, Grate J, Gruber J, Whitman JC, Sheldon RA, Huisman GW. Nature Biotechnol. 2007; 25: 338

• 31 Röthlisberger D, Khersonsky O, Wollacott AM, Jiang L, DeChancie J, Betker J, Gallaher JL, Althoff EA, Zanghellini A, Dym O, Albeck S, Houk KN, Tawfik DS, Baker D. Nature (London) 2008; 453: 190

• 32 Jiang L, Althoff EA, Clemente FR, Doyle L, Röthlisberger D, Zanghellini A, Gallaher JL, Betker JL, Tanaka F, Barbas III CF, Hilvert D, Houk KN, Stoddard BL, Baker D. Science (Washington, D. C.) 2008; 319: 1387

• 33 Biotechnology. Rehm H.-J, Reed G, Pühler A, Stadler D. Wiley-VCH; Weinheim: Germany 1998. 8a.

• 34 Biotechnology. Rehm H.-J, Reed G, Pühler A, Stadler D. Wiley-VCH; Weinheim, Germany 2000. 8b.

• 35 Ladner WE, Whitesides GM. J. Am. Chem. Soc. 1984; 106: 7250

• 36 Phythian SJ, Biotechnology Rehm H.-J, Reed G, Pühler A, Stadler D. Wiley-VCH Weinheim: Germany 1998; 8a. 193–241

• 37 Lam LKP, Hui RAHF, Jones JB. J. Org. Chem. 1986; 51: 2047

• 38 Hummel A, Bruesehaber E, Boettcher D, Trauthwein H, Doderer K, Bornscheuer UT. Angew. Chem. Int. Ed. 2007; 46: 8492

• 39 Bornscheuer U, Boettcher D, Bruesehaber E, Doderer K. US 20 100 021 964, 2010 Chem. Abstr.. 2010

• 40 Volontè F, Pisanelli I, DʼArrigo P, Viani F, Molla G, Servi S, Pollegioni L. Enzyme Microb. Technol. 2011; 49: 560

• 41 Tallarita E, Pollegioni L, Servi S, Molla G. Protein Expression Purif. 2012; 82: 345

• 42 Gentile A, Giordano C, Fuganti C, Ghirotto L, Servi S. J. Org. Chem. 1992; 57: 6635

• 43 Ghirotto L, Servi S, Fuganti C, Gentile A, Giordano C. DE 4 115 697, 1991 Chem. Abstr.. 1992

• 44 Hulshof LA, Roskam JH. EP 343 714A1, 1989 Chem. Abstr.. 1990

• 45 Dodds DR, Lopez JL, Zepp CM, Brandt S. US 6 521 445, 2003 Chem. Abstr.. 2003

• 46 Harrison FG, Gibson ED. Process Biochem. Int. 1984; 19: 33

• 47 Baldaro E, Fuganti C, Servi S, Tagliani A, Terreni M, Microbial Reagents in Organic Synthesis Servi S. Springer Berlin 1992; 175–188

• 48 Pollegioni L, Rosini E, Molla G. Appl. Microbiol. Biotechnol. 2013; 97: 2341

• 49 Olivieri R, Viglia A, Degen L, Angelini L, Fascetti E. DE 2 920 963, 1979 Chem. Abstr.. 1980

• 50 Gavagan JE, DiCosimo R, Eisenberg A, Fager SK, Folsom PW, Hann EC, Schneider KJ, Fallon RD. Appl. Microbiol. Biotechnol. 1999; 52: 654

• 51 Hann EC, Eisenberg A, Fager SK, Perkins NE, Gallagher FG, Cooper SM, Gavagan JE, Stieglitz B, Hennessey SM, DiCosimo R. Bioorg. Med. Chem. 1999; 7: 2239

• 52 Petersen M, Kiener A. Green Chem. 1999; 1: 99

• 53 Hilterhaus L, Liese A, White Biotechnology Ulber R, Sell D. Springer Berlin 2007; 105. 133–173

• 54 Industrial Biotransformations. Liese A, Seelbach K, Wandrey C. Wiley-VCH; Weinheim, Germany 2006

• 55 Yamada H, Kobayashi M. Biosci., Biotechnol., Biochem. 1996; 60: 1391

• 56 Suzuki T, Komatsu K, Tuzimura K. J. Chromatogr., A 1973; 80: 199

• 57 Huisman GW, Liang J, Krebber A. Curr. Opin. Chem. Biol. 2010; 14: 122

• 58 Hollmann F, Arends IWCE, Holtmann D. Green Chem. 2011; 13: 2285

• 59 Hollmann F, Arends IWCE, Buehler K, Schallmey A, Bühler B. Green Chem. 2011; 13: 226

• 60 Rodriguez C, Lavandera I, Gotor V. Curr. Org. Chem. 2012; 16: 2525

• 61 Huisman GW, Collier SJ. Curr. Opin. Chem. Biol. 2013; 17: 284

• 62 Willetts AJ, Knowles CJ, Levitt MS, Roberts SM, Sandey H, Shipston NF. J. Chem. Soc., Perkin Trans. 1 1991; 1608

• 63 Bisogno FR, Rioz-Martínez A, Rodríguez C, Lavandera I, de Gonzalo G, Torres Pazmiño DE, Fraaije MW, Gotor V. ChemCatChem 2010; 2: 946

• 64 Zhang W, OʼConnor K, Wang DIC, Li Z. Appl. Environ. Microbiol. 2009; 75: 687

• 65 Park HJ, Jung J, Choi H, Uhm KN, Kim H.-K. J. Microbiol. Biotechnol. 2010; 20: 1300

• 66 Richter N, Neumann M, Liese A, Wohlgemuth R, Weckbecker A, Eggert T, Hummel W. Biotechnol. Bioeng. 2010; 106: 541

• 67 Torres Pazmiño DE, Snajdrova R, Baas B.-J, Ghobrial M, Mihovilovic MD, Fraaije MW. Angew. Chem. Int. Ed. 2008; 47: 2275

• 68 Torres Pazmiño DE, Riebel A, de Lange J, Rudroff F, Mihovilovic MD, Fraaije MW. ChemBioChem 2009; 10: 2595

• 69 Weckbecker A, Gröger H, Hummel W. Biosystems Engineering I: Creating Superior Biocatalysts Springer Berlin 2010; 120. 195–242

• 70 Kratzer R, Pukl M, Egger S, Nidetzky B. Microb. Cell. Fact. 2008; 7: 37

• 71 Gröger H, May O, Werner H, Menzel A, Altenbuchner J. Org. Process Res. Dev. 2006; 10: 666

• 72 Ager D, Handbook of Chiral Chemicals Ager D. CRC Boca Raton, FL 2005; 11

• 73 Bommarius AS, Schwarm M, Stingl K, Kottenhahn M, Huthmacher K, Drauz K. Tetrahedron: Asymmetry 1995; 6: 2851

• 74 Schmidt E, Blaser H, Fauquex P, Sedelmeier G, Spindler F, Microbial Reagents in Organic Synthesis Servi S. Springer Berlin 1992; 377–388

• 75 Bradshaw CW, Wong C.-H, Hummel W, Kula M.-R. Bioorg. Chem. 1991; 19: 29

• 76 Hilker I, Gutiérrez MC, Furstoss R, Ward J, Wohlgemuth R, Alphand V. Nature Protoc. 2008; 3: 546

• 77 Berezina N, Kozma E, Furstoss R, Alphand V. Adv. Synth. Catal. 2007; 349: 2049

• 78 Hilker I, Wohlgemuth R, Alphand V, Furstoss R. Biotechnol. Bioeng. 2005; 92: 702

• 79 Oberleitner N, Peters C, Muschiol J, Kadow M, Saß S, Bayer T, Schaaf P, Iqbal N, Rudroff F, Mihovilovic MD, Bornscheuer UT. ChemCatChem 2013; 5: 3524

• 80 Mihovilovic MD, Müller B, Kayser MM, Stewart JD, Fröhlich J, Stanetty P, Spreitzer H. J. Mol. Catal. B: Enzym. 2001; 11: 349

• 81 Mihovilovic MD, Chen G, Wang S, Kyte B, Rochon F, Kayser MM, Stewart JD. J. Org. Chem. 2001; 66: 733

• 82 Stewart JD, Reed KW, Martinez CA, Zhu J, Chen G, Kayser MM. J. Am. Chem. Soc. 1998; 120: 3541

• 83 Stewart JD. Curr. Org. Chem. 1998; 2: 195

• 84 Fink MJ, Rudroff F, Mihovilovic MD. Bioorg. Med. Chem. Lett. 2011; 21: 6135

• 85 Fink MJ, Fischer TC, Rudroff F, Dudek H, Fraaije MW, Mihovilovic MD. J. Mol. Catal. B: Enzym. 2011; 73: 9

• 86 Rehdorf J, Mihovilovic MD, Bornscheuer UT. Angew. Chem. Int. Ed. 2010; 49: 4506

• 87 Rehdorf J, Lengar A, Bornscheuer UT, Mihovilovic MD. Bioorg. Med. Chem. Lett. 2009; 19: 3739

• 88 Mihovilovic MD. Curr. Org. Chem. 2006; 10: 1265

• 89 Zhang Z.-G, Roiban G.-D, Acevedo JP, Polyak I, Reetz MT. Adv. Synth. Catal. 2013; 355: 99

• 90 Zhang Z.-G, Parra LP, Reetz MT. Chem.–Eur. J. 2012; 18: 10160

• 91 Opperman DJ, Reetz MT. ChemBioChem 2010; 11: 2589

• 92 Hollmann F, Taglieber A, Schulz F, Reetz MT. Angew. Chem. Int. Ed. 2007; 46: 2903

• 93 Clouthier CM, Kayser MM, Reetz MT. J. Org. Chem. 2006; 71: 8431

• 94 Schulz F, Leca F, Hollmann F, Reetz MT. Beilstein J. Org. Chem. 2005; 1: 10

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

• 96 Reetz MT, Brunner B, Schneider T, Schulz F, Clouthier CM, Kayser MM. Angew. Chem. Int. Ed. 2004; 43: 4075

• 97 Alphand V, Wohlgemuth R. Curr. Org. Chem. 2010; 14: 1928

• 98 Bong YK, Clay MD, Collier SJ, Mijts B, Vogel M, Zhang X, Zhu J, Nazor J, Smith D, Song S. WO 2011 071 982, 2011 Chem. Abstr.. 2011

• 99 Ang EL, Clay MD, Behrouzian B, Eberhard E, Collier SJ, Fu FJ, Smith D, Song S, Alvizio O, Widegren M, Zhu J, Xu J, Wilson R Vol WO 2 012 078 800, 2012 Chem. Abstr.. 2012

• 100 Koszelewski D, Tauber K, Faber K, Kroutil W. Trends Biotechnol. 2010; 28: 324

• 101 Savile CK, Janey JM, Mundorff EC, Moore JC, Tam S, Jarvis WR, Colbeck JC, Krebber A, Fleitz FJ, Brands J, Devine PN, Huisman GW, Hughes GJ. Science (Washington, D. C.) 2010; 329: 305

• 102 Desai AA. Angew. Chem. Int. Ed. 2011; 50: 1974

• 103 www.epa.gov/gcc/pubs/pgcc/winners/gspa06.html (accessed Sept 25, 2014).

• 104 Bruggink A, Roos EC, de Vroom E. Org. Process Res. Dev. 1998; 2: 128

• 105 Clausen K, Dekkers RM. WO 9 602 663, 1996 Chem. Abstr.. 1996

• 106 Oyama K, Nishimura S, Nonaka Y, Kihara K, Hashimoto T. J. Org. Chem. 1981; 46: 5241

• 107 Adelhorst K, Björkling F, Godtfredsen SE, Kirk O. Synthesis 1990; 112

• 108 Björkling F, Godtfredsen SE, Kirk O. J. Chem. Soc., Chem. Commun. 1990; 1301

• 109 Thum O. Tenside, Surfactants, Deterg. 2004; 41: 287

• 110 Thum O, Oxenbøll KM. SOFW J. 2008; 134: 44

• 111 Thum O, Oxenbøll KM. Biocatalysis; A sustainable process for production of cosmetic ingredients. In Proceedings of the International Federation of Societies of Cosmetic Chemists. IFSCC Congress 2006.

• 112 de Ferra L, Massardo P, Piccolo O, Servi S. EP 0 776 976, 1997 Chem. Abstr.. 1997

• 113 DʼArrigo P, Servi S. Trends Biotechnol. 1997; 15: 90

• 114 DʼArrigo P, de Ferra L, Piergianni V, Selva A, Servi S, Strini A. J. Chem. Soc., Perkin Trans. 1 1996; 2651

• 115 Rios-Mercadillo VM, Whitesides GM. J. Am. Chem. Soc. 1979; 101: 5828

• 116 Schoevaart R, van Rantwijk F, Sheldon RA. J. Org. Chem. 2000; 65: 6940

• 117 DʼArrigo P, Piergianni V, Pedrocchi-Fantoni G, Servi S. J. Chem. Soc., Chem. Commun. 1995; 2505

• 118 Kieslich K. Microbial Transformations of Non-steroid Cyclic Compounds. Thieme; Stuttgart 1976

• 119 Martzen MR, McCraith SM, Spinelli SL, Torres FM, Fields S, Grayhack EJ, Phizicky EM. Science (Washington, D. C.) 1999; 286: 1153

• 120 Fronza G, Fuganti C, Grasselli P, Servi S, Zucchi G, Barbeni M, Villa M. J. Chem. Soc., Chem. Commun. 1995; 439

• 121 Wipf B, Kupfer E, Bertazzi R, Leuenberger HGW. Helv. Chim. Acta 1983; 66: 485

• 122 VanMiddlesworth F, Sih CJ. Biocatal. Biotransform. 1987; 1: 117

• 123 Sih CJ, Zhou B.-N, Gopalan AS, Shieh W.-R, Chen C.-S, Girdaukas G, VanMiddlesworth F. Ann. N. Y. Acad. Sci. 1984; 434: 186

• 124 Zhou B.-N, Gopalan AS, VanMiddlesworth F, Shieh W.-R, Sih CJ. J. Am. Chem. Soc. 1983; 105: 5925

• 125 Nakamura K, Kawai Y, Nakajima N, Ohno A. J. Org. Chem. 1991; 56: 4778

• 126 Nakamura K, Kawai Y, Oka S, Ohno A. Bull. Chem. Soc. Jpn. 1989; 62: 875

• 127 Rodríguez S, Kayser M, Stewart JD. Org. Lett. 1999; 1: 1153

• 128 Rodríguez S, Kayser MM, Stewart JD. J. Am. Chem. Soc. 2001; 123: 1547

• 129 Stewart JD, Rodríguez S, Kayser MM, Enzyme Technologies for Pharmaceutical and Biotechnological Applications Kirst HA, Yeh W.-K, Zmijewski Jr MJ. Marcel Dekker New York 2001; 175–207

• 130 Kaluzna IA, Matsuda T, Sewell AK, Stewart JD. J. Am. Chem. Soc. 2004; 126: 12827

• 131 Ma SK, Gruber J, Davis C, Newman L, Gray D, Wang A, Grate J, Huisman GW, Sheldon RA. Green Chem. 2010; 12: 81

• 132 Liang J, Lalonde J, Borup B, Mitchell V, Mundorff E, Trinh N, Kochrekar DA, Nair Cherat R, Pai GG. Org. Process Res. Dev. 2010; 14: 193

• 133 Fuganti C, Chiringhelli D, Grasselli P. J. Chem. Soc., Chem. Commun. 1975; 846b

• 134 Leuenberger HGW, Boguth W, Barner R, Schmid M, Zell R. Helv. Chim. Acta 1979; 62: 455

• 135 Gramatica P, Ranzi BM, Manitto P. Bioorg. Chem. 1981; 10: 14

• 136 Desrut M, Kergomard A, Renard MF, Veschambre H. Tetrahedron 1981; 37: 3825

• 137 Rambeck B, Simon H. Angew. Chem. Int. Ed. Engl. 1974; 13: 609

• 138 Thanos I, Simon H. Angew. Chem. Int. Ed. Engl. 1986; 25: 462

• 139 Warburg O, Christian W. Naturwissenschaften 1932; 20: 688

• 140 Warburg O, Christian W. Biochem. Z. 1933; 266: 377

• 141 Kohli RM, Massey V. J. Biol. Chem. 1998; 273: 32763

• 142 Brown BJ, Deng Z, Karplus PA, Massey V. J. Biol. Chem. 1998; 273: 32753

• 143 Shimoda K, Hirata T. J. Mol. Catal. B: Enzym. 2000; 8: 255

• 144 Kataoka M, Kotaka A, Thiwthong R, Wada M, Nakamori S, Shimizu S. J. Biotechnol. 2004; 114: 1

• 145 Shimoda K, Kubota N, Hamada H, Kaji M, Hirata T. Tetrahedron: Asymmetry 2004; 15: 1677

• 146 Swiderska MA, Stewart JD. J. Mol. Catal. B: Enzym. 2006; 42: 52

• 147 Swiderska MA, Stewart JD. Org. Lett. 2006; 8: 6131

• 148 Hall M, Stueckler C, Kroutil W, Macheroux P, Faber K. Angew. Chem. Int. Ed. 2007; 46: 3934

• 149 Leuenberger HGW, Boguth W, Widmer E, Zell R. Helv. Chim. Acta 1976; 59: 1832

• 150 Högberg H.-E, Hedenström E, Fägerhag J, Servi S. J. Org. Chem. 1992; 57: 2052

• 151 Hall M, Stueckler C, Hauer B, Stuermer R, Friedrich T, Breuer M, Kroutil W, Faber K. Eur. J. Org. Chem. 2008; 1511

• 152 Evans DA, Ennis MD, Mathre DJ. J. Am. Chem. Soc. 1982; 104: 1737

• 153 Holmberg E, Holmquist M, Hedenström E, Berglund P, Norin T, Högberg H.-E, Hult K. Appl. Microbiol. Biotechnol. 1991; 35: 572

• 154 Bougioukou DJ, Walton AZ, Stewart JD. Chem. Commun. (Cambridge) 2010; 46: 8558

• 155 Liese A, Seelbach K, Buchholz A, Haberland J, Industrial Biotransformations Liese A, Seelbach K, Wandrey C. Wiley-VCH Weinheim, Germany 2006; 447

• 156 Fuganti C, Grasselli P, Poli G, Servi S, Zorzella A. J. Chem. Soc., Chem. Commun. 1988; 1619

• 157 Fuganti C, Grasselli P, Biocatalysis in Agricultural Biotechnology Whitaker JR, Sonnet PE. 389 American Chemical Society Washington, DC 1989; 359

• 158 Cardillo R, Servi S, Tinti C. Appl. Microbiol. Biotechnol. 1991; 36: 300

• 159 Meyer D, Walter L, Kolter G, Pohl M, Müller M, Tittmann K. J. Am. Chem. Soc. 2011; 133: 3609

• 160 Bujons J, Guajardo R, Kyler KS. J. Am. Chem. Soc. 1988; 110: 604

• 161 Glänzer BI, Faber K, Griengl H. Tetrahedron 1987; 43: 5791

• 162 Becker W, Freund H, Pfeil E. Angew. Chem. Int. Ed. Engl. 1965; 4: 1079

• 163 Effenberger F, Ziegler T, Förster S. Angew. Chem. Int. Ed. Engl. 1987; 26: 458

• 164 Effenberger F, Hörsch B, Förster S, Ziegler T. Tetrahedron Lett. 1990; 31: 1249

• 165 Klempier N, Griengl H, Hayn M. Tetrahedron Lett. 1993; 34: 4769

• 166 Förster S, Roos J, Effenberger F, Wajant H, Sprauer A. Angew. Chem. Int. Ed. Engl. 1996; 35: 437

• 167 Hasslacher M, Schall M, Hayn M, Griengl H, Kohlwein SD, Schwab H. J. Biol. Chem. 1996; 271: 5884

• 168 Griengl H, Klempier N, Pöchlauer P, Schmidt M, Shi N, Zabelinskaja-Mackova AA. Tetrahedron 1998; 54: 14477

• 169 Kazlauskas RJ, Bornscheuer UT, Biotechnology Rehm H.-J, Reed G, Pühler A, Stadler D. Wiley-VCH Weinheim: Germany 1998; 8a. 36–191

• 170 Wang Y.-F, Lalonde JJ, Momongan M, Bergbreiter DE, Wong C.-H. J. Am. Chem. Soc. 1988; 110: 7200

• 171 Barbas III CF, Wang Y.-F, Wong C.-H. J. Am. Chem. Soc. 1990; 112: 2013

• 172 Jennewein S, Schürmann M, Wolberg M, Hilker I, Luiten R, Wubbolts M, Mink D. Biotechnol. J. 2006; 1: 537

• 173 Schürmann M, Sprenger GA. J. Biol. Chem. 2001; 276: 11055

• 174 Patel JM. J. Mol. Catal. B: Enzym. 2009; 61: 123