1.4.3 Hydrolysis of Amides

M. Hall; K. Faber; G. Tasnádi

doi:10.1055/sos-SD-214-00231

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Faber, K. et al.: 2015 Science of Synthesis, 1: Biocatalysis in Organic Synthesis 1 DOI: 10.1055/sos-SD-214-00231

Biocatalysis in Organic Synthesis 1

1.4.3 Hydrolysis of Amides

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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

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Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

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Abstract

This chapter describes the enzymatic hydrolysis of amide substrates. The main target compounds are amino acids, obtained via the kinetic resolution of amino acid amides and N-acylated amino acids using aminopeptidases, amidases, and aminoacylases. In addition, methods leading to enantiopure carboxylic acids and amines as well as lactamase-catalyzed processes are presented.

Key words

amide hydrolysis - amino acids - amines - carboxamides - lactams - Vince lactam - amidases - aminopeptidases - aminoacylases - lactamases

1 The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science. Greenberg A, Breneman CM, Liebman JF. Wiley; Hoboken, NJ 2003

Search in Google Scholar

2 Leuchtenberger W, Huthmacher K, Drauz K. Appl. Microbiol. Biotechnol. 2005; 69: 1

PubMed Search in Google Scholar

3 Faber K. Biotransformations in Organic Chemistry. Springer; Berlin 2011

Crossref Search in Google Scholar

4 Sonke T, Kaptein B, Schoemaker HE, Amino Acids, Peptides and Proteins in Organic Chemistry Hughes AB. Wiley-VCH Weinheim, Germany 2009; 1. 79

Search in Google Scholar

5 Breuer M, Ditrich K, Habicher T, Hauer B, Keßeler M, Stürmer R, Zelinski T. Angew. Chem. Int. Ed. 2004; 43: 788

PubMed Search in Google Scholar

6 Fournand D, Arnaud A. J. Appl. Microbiol. 2001; 91: 381

PubMed Search in Google Scholar

7 Martínková L, Křen V. Biocatal. Biotransform. 2002; 20: 73

Search in Google Scholar

8 Sharma M, Sharma NN, Bhalla TC. Rev. Environ. Sci. Bio/Technol. 2009; 8: 343

Search in Google Scholar

9 Shaw NM, Robins KT, Kiener A. Adv. Synth. Catal. 2003; 345: 425

Search in Google Scholar

10 Laumen K, Kittelmann M, Ghisalba O. J. Mol. Catal. B: Enzym. 2002; 19–20: 55

Search in Google Scholar

11 Phillips GT, Shears JH. EP 399 589, 1990 Chem. Abstr.. 1991

PubMed Search in Google Scholar

12 Shimizu S, Ogawa J, Chung MC.-M, Yamada H. Eur. J. Biochem. 1992; 209: 375

PubMed Search in Google Scholar

13 Ogawa J, Shimizu S, Yamada H. Bioorg. Med. Chem. 1994; 2: 429

PubMed Search in Google Scholar

14 Shimizu S, Ogawa J, Yamada H. Appl. Microbiol. Biotechnol. 1992; 37: 164

Search in Google Scholar

15 Fuganti C, Grasselli P, Seneci PF, Servi S, Casati P. Tetrahedron Lett. 1986; 27: 2061

Search in Google Scholar

16 Fadnavis NW, Sharfuddin M, Vadivel SK. Tetrahedron: Asymmetry 1999; 10: 4495

Search in Google Scholar

17 Torres-Gavilán A, Castillo E, López-Munguía A. J. Mol. Catal. B: Enzym. 2006; 41: 136

Search in Google Scholar

18 Smidt H, Fischer A, Fischer P, Schmid RD, Stelzer U. DE 19 507 217, 1996 Chem. Abstr.. 1996

PubMed Search in Google Scholar

19 Sonke T, Kaptein B, Wagner AFV, Quaedflieg PJLM, Schultz S, Ernste S, Schepers A, Mommers JHM, Broxterman QB. J. Mol. Catal. B: Enzym. 2004; 29: 265

Search in Google Scholar

20 Kadereit D, Waldmann H. Chem. Rev. 2001; 101: 3367

PubMed Search in Google Scholar

21 Wuts PGM, Greene TW. Greeneʼs Protective Groups in Organic Synthesis. Wiley; Hoboken, NJ 2006

Crossref Search in Google Scholar

22 Kohls H, Steffen-Munsberg F, Höhne M. Curr. Opin. Chem. Biol. 2014; 19: 180

PubMed Search in Google Scholar

23 Schoemaker HE, Boesten WHJ, Kaptein B, Roos EC, Broxterman QB, van den Tweel WJJ, Kamphuis J. Acta Chem. Scand. 1996; 50: 225

Search in Google Scholar

24 Hermes HFM, Sonke T, Peters PJH, van Balken JAM, Kamphuis J, Dijkhuizen L, Meijer EM. Appl. Environ. Microbiol. 1993; 59: 4330

PubMed Search in Google Scholar

25 van den Tweel WJJ, van Dooren TJGM, de Jonge PH, Kaptein B, Duchateau ALL, Kamphuis J. Appl. Microbiol. Biotechnol. 1993; 39: 296

Search in Google Scholar

26 Sonke T, Ernste S, Tandler RF, Kaptein B, Peeters WPH, van Assema FBJ, Wubbolts MG, Schoemaker HE. Appl. Environ. Microbiol. 2005; 71: 7961

PubMed Search in Google Scholar

27 Hermes HFM, Tandler RF, Sonke T, Dijkhuizen L, Meijer EM. Appl. Environ. Microbiol. 1994; 60: 153

PubMed Search in Google Scholar

28 Kamphuis J, Boesten WHJ, Broxterman QB, Hermes HFM, van Balken JAM, Meijer EM, Schoemaker HE. Adv. Biochem. Eng./Biotechnol. 1990; 42: 133

PubMed Search in Google Scholar

29 Boesten WHJ, Cals MJH. US 4 705 752, 1987 Chem. Abstr.. 1986

PubMed Search in Google Scholar

30 Wolf LB, Sonke T, Tjen KCMF, Kaptein B, Broxterman QB, Schoemaker HE, Rutjes FPJT. Adv. Synth. Catal. 2001; 343: 662

Search in Google Scholar

31 Kaptein B, van Dooren TJGM, Boesten WHJ, Sonke T, Duchateau ALL, Broxterman QB, Kamphuis J. Org. Process Res. Dev. 1998; 2: 10

Search in Google Scholar

32 Ozaki A, Kawasaki H, Yagasaki M, Hashimoto Y. Biosci., Biotechnol., Biochem. 1992; 56: 1980

Search in Google Scholar

33 Ozaki A, Kawasaki H, Hashimoto Y, Tamura K, Ochiai K, Kawamoto I. EP 334 358, 1989 Chem. Abstr.. 1990

PubMed Search in Google Scholar

34 Asano Y, Yamaguchi S. J. Am. Chem. Soc. 2005; 127: 7696

PubMed Search in Google Scholar

35 Youshko MI, van Langen LM, Sheldon RA, Švedas VK. Tetrahedron: Asymmetry 2004; 15: 1933

Search in Google Scholar

36 Roos EC, Mooiweer HH, Hiemstra H, Speckamp WN, Kaptein B, Boesten WHJ, Kamphuis J. J. Org. Chem. 1992; 57: 6769

Search in Google Scholar

37 Tornøe CW, Sonke T, Maes I, Schoemaker HE, Meldal M. Tetrahedron: Asymmetry 2000; 11: 1239

Search in Google Scholar

38 Sonke T, Kaptein B, Boesten WHJ, Broxterman QB, Kamphuis J, Formaggio F, Toniolo C, Rutjes FPJT, Schoemaker HE, Stereoselective Biocatalysis Patel RN. Marcel Dekker New York 2000; 23

39 Vriesema BK, ten Hoeve H, Wynberg H, Kellogg RM, Boesten WHJ, Meijer EM, Schoemaker HE. Tetrahedron Lett. 1986; 27: 2045

Search in Google Scholar

40 Kruizinga WH, Bolster J, Kellogg RM, Kamphuis J, Boesten WHJ, Meijer EM, Schoemaker HE. J. Org. Chem. 1988; 53: 1826

Search in Google Scholar

41 Kaptein B, Boesten WHJ, Broxterman QB, Peters PJH, Schoemaker HE, Kamphuis J. Tetrahedron: Asymmetry 1993; 4: 1113

Search in Google Scholar

42 Koksch B, Quaedflieg PJLM, Michel T, Burger K, Broxterman QB, Schoemaker HE. Tetrahedron: Asymmetry 2004; 15: 1401

Search in Google Scholar

43 Peggion C, Flammengo R, Mossel E, Broxterman QB, Kaptein B, Kamphuis J, Formaggio F, Crisma M, Toniolo C. Tetrahedron 2000; 56: 3589

Search in Google Scholar

44 Storcken RPM, Panella L, van Delft FL, Kaptein B, Broxterman QB, Schoemaker HE, Rutjes FPJT. Adv. Synth. Catal. 2007; 349: 161

Search in Google Scholar

45 Kaptein B, Broxterman QB, Schoemaker HE, Rutjes FPJT, Veerman JJN, Kamphuis J, Peggion C, Formaggio F, Toniolo C. Tetrahedron 2001; 57: 6567

Search in Google Scholar

46 Kaptein B, Moody HM, Broxterman QB, Kamphuis J. J. Chem. Soc., Perkin Trans. 1 1994; 1495

47 Jost M, Sonke T, Kaptein B, Broxterman QB, Sewald N. Synthesis 2005; 272

48 Van Betsbrugge J, Tourwé D, Kaptein B, Kierkels H, Broxterman R. Tetrahedron 1997; 53: 9233

Search in Google Scholar

49 Sheldon RA, Arends IWCE, Hanefeld U. Green Chemistry and Catalysis. Wiley-VCH; Weinheim, Germany 2007

Crossref Search in Google Scholar

50 Chenault HK, Dahmer J, Whitesides GM. J. Am. Chem. Soc. 1989; 111: 6354

Search in Google Scholar

51 Bommarius AS, Drauz K, Günther K, Knaup G, Schwarm M. Tetrahedron: Asymmetry 1997; 8: 3197

Search in Google Scholar

52 Beller M, Eckert M, Geissler H, Napierski B, Rebenstock H.-P, Holla EW. Chem.–Eur. J. 1998; 4: 935

Search in Google Scholar

53 Gröger H, Trauthwein H, Buchholz S, Drauz K, Sacherer C, Godfrin S, Werner H. Org. Biomol. Chem. 2004; 2: 1977

PubMed Search in Google Scholar

54 Chibata I, Tosa T, Sato T, Mori T. Methods Enzymol. 1976; 44: 746

PubMed Search in Google Scholar

55 Tosa T, Mori T, Fuse N, Chibata I. Agric. Biol. Chem. 1969; 33: 1047

Search in Google Scholar

56 Leuchtenberger W, Karrenbauer M, Plöcker ULF. Ann. N. Y. Acad. Sci. 1984; 434: 78

Search in Google Scholar

57 Bommarius AS, Drauz K, Klenk H, Wandrey C. Ann. N. Y. Acad. Sci. 1992; 672: 126

PubMed Search in Google Scholar

58 Petersen M, Sauter M. Chimia 1999; 53: 608

Search in Google Scholar

59 May O, Verseck S, Bommarius A, Drauz K. Org. Process Res. Dev. 2002; 6: 452

Search in Google Scholar

60 Tokuyama S, Hatano K. Appl. Microbiol. Biotechnol. 1996; 44: 774

PubMed Search in Google Scholar

61 Baxter S, Royer S, Grogan G, Brown F, Holt-Tiffin KE, Taylor IN, Fotheringham IG, Campopiano DJ. J. Am. Chem. Soc. 2012; 134: 19310

PubMed Search in Google Scholar

62 Moriguchi M, Ideta K. Appl. Environ. Microbiol. 1988; 54: 2767

PubMed Search in Google Scholar

63 Konda-Yamada Y, Okada C, Yoshida K, Umeda Y, Arima S, Sato N, Kai T, Takayanagi H, Harigaya Y. Tetrahedron 2002; 58: 7851

Search in Google Scholar

64 Wakayama M, Yoshimune K, Hirose Y, Moriguchi M. J. Mol. Catal. B: Enzym. 2003; 23: 71

Search in Google Scholar

65 Kumagai S, Kobayashi M, Yamaguchi S, Kanaya T, Motohashi R, Isobe K. J. Mol. Catal. B: Enzym. 2004; 30: 159

Search in Google Scholar

66 Arroyo M, de la Mata I, Acebal C, Pilar Castillón M. Appl. Microbiol. Biotechnol. 2003; 60: 507

PubMed Search in Google Scholar

67 Volpato G, Rodrigues RC, Fernandez-Lafuente R. Curr. Med. Chem. 2010; 17: 3855

PubMed Search in Google Scholar

68 Srirangan K, Orr V, Akawi L, Westbrook A, Moo-Young M, Chou CP. Biotechnol. Adv. 2013; 31: 1319

PubMed Search in Google Scholar

69 Pathak T, Waldmann H. Curr. Opin. Chem. Biol. 1998; 2: 112

PubMed Search in Google Scholar

70 Grulich M, Štěpánek V, Kyslík P. Biotechnol. Adv. 2013; 31: 1458

PubMed Search in Google Scholar

71 Švedas VK, Savchenko MV, Beltser AI, Guranda DF. Ann. N. Y. Acad. Sci. 1996; 799: 659

PubMed Search in Google Scholar

72 Fadnavis NW, Sharfuddin M, Vadivel SK, Bhalerao UT. J. Chem. Soc., Perkin Trans. 1 1997; 3577

73 Liu SL, Song QX, Wei DZ, Zhang YW, Wang XD. Prep. Biochem. Biotechnol. 2006; 36: 235

PubMed Search in Google Scholar

74 Fadnavis NW, Devi AV, Jasti LS. Tetrahedron: Asymmetry 2008; 19: 2363

Search in Google Scholar

75 Venkataiah M, Reddipalli G, Jasti LS, Fadnavis NW. Tetrahedron: Asymmetry 2011; 22: 1855

Search in Google Scholar

76 Soloshonok VA, Kirilenko AG, Fokina NA, Shishkina IP, Galushko SV, Kukhar VP, Švedas VK, Kozlova EV. Tetrahedron: Asymmetry 1994; 5: 1119

Search in Google Scholar

77 Soloshonok VA, Kirilenko AG, Fokina NA, Kukhar VP, Galushko SV, Švedas VK, Resnati G. Tetrahedron: Asymmetry 1994; 5: 1225

Search in Google Scholar

78 Cardillo G, Tolomelli A, Tomasini C. J. Org. Chem. 1996; 61: 8651

Search in Google Scholar

79 Soloshonok VA, Svedas VK, Kukhar VP, Kirilenko AG, Rybakova AV, Solodenko VA, Fokina NA, Kogut OV, Gulaev IY, Kozlova EV, Shishkina IP, Galushko SV. Synlett 1993; 339

80 Cardillo G, Gentilucci L, Tolomelli A, Tomasini C. J. Org. Chem. 1998; 63: 2351

Search in Google Scholar

81 Topgi RS, Ng JS, Landis B, Wang P, Behling JR. Bioorg. Med. Chem. 1999; 7: 2221

PubMed Search in Google Scholar

82 Margolin AL. Tetrahedron Lett. 1993; 34: 1239

Search in Google Scholar

83 Solodenko VA, Kasheva TN, Kukhar VP, Kozlova EV, Mironenko DA, Švedas VK. Tetrahedron 1991; 47: 3989

Search in Google Scholar

84 Solodenko VA, Belik MY, Galushko SV, Kukhar VP, Kozlova EV, Mironenko DA, Svedas VK. Tetrahedron: Asymmetry 1993; 4: 1965

Search in Google Scholar

85 Wang M.-X, Lu G, Ji G.-J, Huang Z.-T, Meth-Cohn O, Colby J. Tetrahedron: Asymmetry 2000; 11: 1123

Search in Google Scholar

86 Xue Z, Chao Y, Wang D, Wang M, Qian S. J. Ind. Microbiol. Biotechnol. 2011; 38: 1931

PubMed Search in Google Scholar

87 Brunella A, Graf M, Kittelmann M, Laumen K, Ghisalba O. Appl. Microbiol. Biotechnol. 1997; 47: 515

Search in Google Scholar

88 Graf M, Brunella A, Kittelmann M, Laumen K, Ghisalba O. Appl. Microbiol. Biotechnol. 1997; 47: 650

PubMed Search in Google Scholar

89 Wahl P, Walser-Volken P, Laumen K, Kittelmann M, Ghisalba O. Appl. Microbiol. Biotechnol. 1999; 53: 12

Search in Google Scholar

90 Zhang XX, Prata CAH, McIntosh TJ, Barthelemy P, Grinstaff MW. Bioconjugate Chem. 2010; 21: 988

PubMed Search in Google Scholar

91 Wegner MM, Rapoport H. J. Org. Chem. 1978; 43: 3840

Search in Google Scholar

92 Peverali D, Fornaroli M, Velardi F. US 6 518 456, 2003 Chem. Abstr.. 2003

PubMed Search in Google Scholar

93 Singh R, Vince R. Chem. Rev. 2012; 112: 4642

PubMed Search in Google Scholar

94 Venhoff N, Setzer B, Melkaoui K, Walker UA. Antiviral Ther. 2007; 12: 1075

PubMed Search in Google Scholar

95 Holt-Tiffin KE. Chim. Oggi 2009; 27: 23

Search in Google Scholar

96 Dhuppad U, Aravat V, Navhat S, Thomas A, Kadam S. US 8 404 727, 2013 Chem. Abstr.. 2010

PubMed Search in Google Scholar

97 Taylor SJC, Sutherland AG, Lee C, Wisdom R, Thomas S, Roberts SM, Evans C. J. Chem. Soc., Chem. Commun. 1990; 1120

98 Taylor SJC, McCague R, Wisdom R, Lee C, Dickson K, Ruecroft G, OʼBrien F, Littlechild J, Bevan J, Roberts SM, Evans CT. Tetrahedron: Asymmetry 1993; 4: 1117

Search in Google Scholar

99 Forró E, Fülöp F. Eur. J. Org. Chem. 2008; 5263

100 Toogood HS, Brown RC, Line K, Keene PA, Taylor SJC, McCague R, Littlechild JA. Tetrahedron 2004; 60: 711

Search in Google Scholar

101 Zhu SZ, Gong CY, Song DW, Gao SH, Zheng GJ. Appl. Environ. Microbiol. 2012; 78: 7492

PubMed Search in Google Scholar

102 Taylor SJC, Brown RC, Keene PA, Taylor IN. Bioorg. Med. Chem. 1999; 7: 2163

PubMed Search in Google Scholar

103 Assaf Z, Eger E, Vitnik Z, Fabian WMF, Ribitsch D, Guebitz GM, Faber K, Hall M. ChemCatChem 2014; 6: 2517

Search in Google Scholar

104 Straathof AJJ, Jongejan JA. Enzyme Microb. Technol. 1997; 21: 559

Search in Google Scholar

105 Liese A, Seelbach K, Buchholz A, Haberland J, Industrial Biotransformations Liese A, Seelbach K, Wandrey C. Wiley-VCH Weinheim: Germany 2006; 147

Crossref

106 Staudenmaler HR, Hauer B, Balkenhohl F, Ladner W, Schnell U, Pressler U. EP 0 687 736, 1995 Chem. Abstr.. 1996

PubMed Search in Google Scholar

107 Evans C, McCague R, Roberts SM, Sutherland AG, Wisdom R. J. Chem. Soc., Perkin Trans. 1 1991; 2276

108 Forró E, Fülöp F. Chem.–Eur. J. 2006; 12: 2587

PubMed Search in Google Scholar