Download PDF
Faber, K. et al.: 2015 Science of Synthesis, 1: Biocatalysis in Organic Synthesis 1 DOI: 10.1055/sos-SD-214-00250
Biocatalysis in Organic Synthesis 1

1.4.4 Enzymatic Synthesis of Amides

More Information

Book

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

Also available at
 


Abstract

The synthesis of amides is one of the most common reactions performed in organic chemistry. Biocatalysis is an attractive alternative to chemical methodologies because of the mild reaction conditions and excellent atom economy, combined with the potential for stereoselectivity. Here, we provide an overview of the literature on enzyme-catalyzed amide-bond formation on a preparative scale, with a focus on nonnatural substrates.

Key words

amines - amides - esters - aminolysis - enzymes - regioselectivity - chemoselectivity - stereoselectivity - kinetic resolution - lipases - esterases - penicillin acylases - proteases - nitrile hydratases
 
  • 1 Carey JS, Laffan D, Thomson C, Williams MT. Org. Biomol. Chem. 2006; 4: 2337
    PubMed
  • 2 Gotor V, Gotor-Fernández V, Busto E, Comprehensive Chirality Carreira EM, Yamamoto H. Elsevier Amsterdam, The Netherlands 2012; 7. 101
    Crossref
  • 3 Pattabiraman VR, Bode JW. Nature (London) 2011; 480: 471
  • 4 Gotor-Fernández V, Brieva R, Gotor V. J. Mol. Catal. B: Enzym. 2006; 40: 111
  • 5 Ollis DL, Cheah E, Cygler M, Dijkstra B, Frolow F, Franken SM, Harel M, Remington SJ, Silman I, Schrag J, Sussman JL, Verschueren KHG, Goldman A. Protein Eng. 1992; 5: 197
  • 6 Neang PM, Subileau M, Perrier V, Dubreucq E. J. Mol. Catal. B: Enzym. 2013; 94: 36
  • 7 van Rantwijk F, Hacking MAPJ, Sheldon RA. Monatsh. Chem. 2000; 131: 549
  • 8 Reetz MT. Curr. Opin. Chem. Biol. 2002; 6: 145
    PubMed
  • 9 Ghanem A. Tetrahedron 2007; 63: 1721
  • 10 Lutz S. Tetrahedron: Asymmetry 2004; 15: 2743
  • 11 Gotor-Fernández V, Busto E, Gotor V. Adv. Synth. Catal. 2006; 348: 797
  • 12 Torres-Gavilán A, Castillo E, López-Munguía A. J. Mol. Catal. B: Enzym. 2006; 41: 136
  • 13 Syrén P.-O, Hult K. ChemCatChem 2011; 3: 853
  • 14 Schmid RD, Verger R. Angew. Chem. Int. Ed. 1998; 37: 1608
    PubMed
  • 15 Zaks A, Klibanov AM. Proc. Natl. Acad. Sci. U. S. A. 1985; 82: 3192
    PubMed
  • 16 Adamczyk M, Grote J. Tetrahedron Lett. 1996; 37: 7913
  • 17 Adamczyk M, Grote J. Tetrahedron: Asymmetry 1997; 8: 2099
  • 18 Adamczyk M, Grote J, Rege S. Tetrahedron: Asymmetry 1997; 8: 2509
  • 19 Adamczyk M, Grote J. Bioorg. Med. Chem. Lett. 1999; 9: 245
  • 20 Conde S, López-Serrano P, Martínez A. Tetrahedron: Asymmetry 2000; 11: 2537
  • 21 Gotor V, Brieva R, Rebolledo F. J. Chem. Soc., Chem. Commun. 1988; 957
  • 22 Kanerva LT, Kosonen M, Vänttinen E, Huuhtanen TT, Dahlqvist M. Acta Chem. Scand. 1992; 46: 1101
  • 23 Furutani T, Furui M, Ooshima H, Kato J. Enzyme Microb. Technol. 1996; 19: 578
  • 24 Couturier L, Taupin D, Yvergnaux F. J. Mol. Catal. B: Enzym. 2009; 56: 29
  • 25 Tufvesson P, Annerling A, Hatti-Kaul R, Adlercreutz D. Biotechnol. Bioeng. 2007; 97: 447
    PubMed
  • 27 Madeira Lau R, van Rantwijk F, Seddon KR, Sheldon RA. Org. Lett. 2000; 2: 4189
    PubMed
  • 28 Dhake KP, Qureshi ZS, Singhal RS, Bhanage BM. Tetrahedron Lett. 2009; 50: 2811
  • 29 van Pelt S, Teeuwen RLM, Janssen MHA, Sheldon RA, Dunn PJ, Howard RM, Kumar R, Martínez I, Wong JW. Green Chem. 2011; 13: 1791
  • 30 Lal S, Snape TJ. J. Mol. Catal. B: Enzym. 2012; 83: 80
  • 31 Chen S.-T, Tsai C.-F, Wang K.-T. Chem. Commun. (Cambridge) 1996; 165
  • 32 Hassan S, Tschersich R, Müller TJJ. Tetrahedron Lett. 2013; 54: 4641
  • 33 Stavila E, Loos K. Tetrahedron Lett. 2013; 54: 370
  • 34 Li X.-G, Lähitie M, Kanerva LT. Tetrahedron: Asymmetry 2008; 19: 1857
  • 35 van Rantwijk F, Sheldon RA. Tetrahedron 2004; 60: 501
  • 36 Kazlauskas RJ, Weissfloch ANE, Rappaport AT, Cuccia LA. J. Org. Chem. 1991; 56: 2656
  • 37 Gotor V, Brieva R, Rebolledo F. Tetrahedron Lett. 1988; 29: 6973
  • 38 García-Urdiales E, Ríos-Lombardía N, Mangas-Sánchez J, Gotor-Fernández V, Gotor V. ChemBioChem 2009; 10: 1830
    PubMed
  • 39 Schmid A, Dordick JS, Hauer B, Kiener A, Wubbolts M, Witholt B. Nature (London) 2001; 409: 258
  • 40 Cammenberg M, Hult K, Park S. ChemBioChem 2006; 7: 1745
    PubMed
  • 41 Ditrich K. Synthesis 2008; 2283
  • 42 Morgan B, Zaks A, Dodds DR, Liu J, Jain R, Megati S, Njoroge FG, Girijavallabhan VM. J. Org. Chem. 2000; 65: 5451
    PubMed
  • 43 Morgan B, Dodds DR, Zaks A, Andrews DR, Klesse R. J. Org. Chem. 1997; 62: 7736
  • 44 Shakeri M, Engström K, Sandström AG, Bäckvall J.-E. ChemCatChem 2010; 2: 534
  • 45 Boros Z, Falus P, Márkus M, Weiser D, Oláh M, Hornyánszky G, Nagy J, Poppe L. J. Mol. Catal. B: Enzym. 2013; 85–86: 119
  • 46 de Miranda AS, Miranda LSM, de Souza ROMA. Org. Biomol. Chem. 2013; 11: 3332
    PubMed
  • 47 Raza S, Fransson L, Hult K. Protein Sci. 2001; 10: 329
    PubMed
  • 48 Gotor V, Brieva R, González C, Rebolledo F. Tetrahedron 1991; 47: 9207
  • 49 García MJ, Rebolledo F, Gotor V. Tetrahedron: Asymmetry 1993; 4: 2199
  • 50 García MJ, Rebolledo F, Gotor V. Tetrahedron: Asymmetry 1992; 3: 1519
  • 51 Weiß M, Gröger H. Synlett 2009; 1251
  • 52 Strompen S, Weiß M, Ingram T, Smirnova I, Gröger H, Hilterhaus L, Liese A. Biotechnol. Bioeng. 2012; 109: 1479
    PubMed
  • 53 Strompen S, Weiß M, Gröger H, Hilterhaus L, Liese A. Adv. Synth. Catal. 2013; 355: 2391
  • 54 Turner NJ. Curr. Opin. Chem. Biol. 2004; 8: 114
    PubMed
  • 55 Martín-Matute B, Bäckvall J.-E. Curr. Opin. Chem. Biol. 2007; 11: 226
    PubMed
  • 56 Pellissier H. Adv. Synth. Catal. 2011; 353: 659
  • 57 Pellissier H. Tetrahedron 2008; 64: 1563
  • 58 Paetzold J, Bäckvall J.-E. J. Am. Chem. Soc. 2005; 127: 17620
    PubMed
  • 59 Rodríguez-Mata M, Gotor-Fernández V, González-Sabín J, Rebolledo F, Gotor V. Org. Biomol. Chem. 2011; 9: 2274
    PubMed
  • 60 Kim M.-J, Kim W.-H, Han K, Choi YK, Park J. Org. Lett. 2007; 9: 1157
    PubMed
  • 61 Parvulescu A, De Vos D, Jacobs P. Chem. Commun. (Cambridge) 2005; 5307
    PubMed
  • 62 Stirling M, Blacker J, Page MI. Tetrahedron Lett. 2007; 48: 1247
  • 63 Poulhès F, Vanthuyne N, Bertrand MP, Gastaldi S, Gil G. J. Org. Chem. 2011; 76: 7281
    PubMed
  • 64 Puertas S, Rebolledo F, Gotor V. J. Org. Chem. 1996; 61: 6024
  • 65 López-García M, Alfonso I, Gotor V. Tetrahedron: Asymmetry 2003; 14: 603
  • 66 Busto E, Gotor-Fernández V, Montejo-Bernardo J, Gárcía-Granda S, Gotor V. Org. Lett. 2007; 9: 4203
    PubMed
  • 67 Ríos-Lombardía N, Busto E, Gotor-Fernández V, Gotor V. J. Org. Chem. 2011; 76: 5709
    PubMed
  • 68 Hacking MAPJ, van Rantwijk F, Sheldon RA. J. Mol. Catal. B: Enzym. 2000; 9: 201
  • 69 Shin HC, Quinn DM. Biochemistry 1992; 31: 811
  • 70 Arroyo M, de la Mata I, Acebal C, Castillon MP. Appl. Microbiol. Biotechnol. 2003; 60: 507
    PubMed
  • 71 Bruggink A, Roos EC, de Vroom E. Org. Process Res. Dev. 1998; 2: 128
  • 72 Schulze B, Wubbolts MG. Curr. Opin. Biotechnol. 1999; 10: 609
    PubMed
  • 73 Abian O, Mateo C, Fernández-Lorente G, Guisán JM, Fernández-Lafuente R. Biotechnol. Prog. 2004; 20: 117
    PubMed
  • 74 Kumar D, Bhalla TC. Appl. Microbiol. Biotechnol. 2005; 68: 726
    PubMed
  • 75 Montalbetti CAGN, Falque V. Tetrahedron 2005; 61: 10827
  • 76 Ulijn RV, Baragaña B, Halling PJ, Flitsch SL. J. Am. Chem. Soc. 2002; 124: 10988
    PubMed
  • 77 Hanzawa S, Encyclopedia of Bioprocess Technology: Fermentation, Biocatalysis and Separation Flickinger MC, Drew SW. Wiley-Interscience New York 1999; 201
  • 78 Morihara K. J. Mol. Recognit. 1990; 3: 181
    PubMed
  • 79 Levitsky V, Lozano P, Iborra JL. Biotechnol. Lett. 1999; 21: 595
  • 80 Wang M.-X. Top. Organomet. Chem. 2011; 36: 105
  • 81 Kobayashi M, Shimizu S. Nature Biotechnol. 1998; 16: 733
    PubMed
  • 82 Prasad S, Bhalla TC. Biotechnol. Adv. 2010; 28: 725
    PubMed
  • 83 Pei X, Yang L, Xu G, Wang Q, Wu J. J. Mol. Catal. B: Enzym. 2014; 99: 26
  • 84 van Pelt S, Zhang M, Otten LG, Holt J, Sorokin DY, van Rantwijk F, Black GW, Perry JJ, Sheldon RA. Org. Biomol. Chem. 2011; 9: 3011
    PubMed
  • 85 Ramteke PW, Maurice NG, Joseph B, Wadher BJ. Biotechnol. Appl. Biochem. 2013; 60: 459
    PubMed
  • 86 Chen J, Zheng R.-C, Zheng Y.-G, Shen Y.-C. Adv. Biochem. Eng./Biotechnol. 2009; 113: 33
    PubMed
  • 87 Black GW, Gregson T, McPake CB, Perry JJ, Zhang M. Tetrahedron Lett. 2010; 51: 1639
  • 88 Yamada H, Kobayashi M. Biosci., Biotechnol., Biochem. 1996; 60: 1391
    PubMed
  • 89 DeSantis G, DiCosimo R, Biocatalysis for the Pharmaceutical Industry: Discovery, Development, and Manufacturing Tao JA, Lin G.-Q, Liese A. Wiley Singapore 2009; 153
    Crossref
  • 90 Ashina Y, Suto M, Endo T, Encyclopedia of Industrial Biotechnology: Bioprocess, Bioseparation, and Cell Technology Flickinger MC. Wiley-Interscience New York 2010; 1833
  • 91 Velankar H, Clarke KG, du Preez R, Cowan DA, Burton SG. Trends Biotechnol. 2010; 28: 561
    PubMed
  • 93 Shen Y, Wang M, Li X, Zhang J, Sun H, Luo J. J. Chem. Technol. Biotechnol. 2012; 87: 1396
  • 94 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
    PubMed
  • 95 Ewert C, Lutz-Wahl S, Fischer L. Tetrahedron: Asymmetry 2008; 19: 2573
  • 96 Moran-Ramallal R, Liz R, Gotor V. Org. Lett. 2007; 9: 521
    PubMed
  • 98 Wu Z.-L, Li Z.-Y. Chem. Commun. (Cambridge) 2003; 386
    PubMed
  • 99 Giessen TW, Marahiel MA. FEBS Lett. 2012; 586: 2065
    PubMed
  • 100 Heide L. Nat. Prod. Rep. 2009; 26: 1241
    PubMed
  • 101 Anderle C, Hennig S, Kammerer B, Li S.-M, Wessjohann L, Gust B, Heide L. Chem. Biol. (Oxford, U. K.) 2007; 14: 955
    PubMed
  • 102 Heide L. Biotechnol. Adv. 2009; 27: 1006
    PubMed
  • 103 Funabashi M, Yang Z, Nonaka K, Hosobuchi M, Fujita Y, Shibata T, Chi X, Van Lanen SG. Nature Chem. Biol. 2010; 6: 581
    PubMed
  • 104 Davids T, Schmidt M, Boettcher D, Bornscheuer UT. Curr. Opin. Chem. Biol. 2013; 17: 215
    PubMed
  • 105 Bornscheuer UT, Huisman GW, Kazlauskas RJ, Lutz S, Moore JC, Robins K. Nature (London) 2012; 485: 185