Faber, K. et al.: 2015 Science of Synthesis: Biocatalysis Organic Synthesis 2 DOI: 10.1055/sos-SD-215-00213
Biocatalysis in Organic Synthesis 2

2.4.3 ω-Transaminases

Weitere Informationen

Buch

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

Autoren: 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.

Titel: Biocatalysis Organic Synthesis 2

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

Fachgebiete: Organische Chemie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Typ: Mehrbändiges Werk

 


Abstract

Optically pure amines are prepared from the corresponding prochiral ketones via asymmetric amination employing ω-transaminases and selected amine donors.

 
  • 1 Simon RC, Richter N, Busto E, Kroutil W. ACS Catal. 2014; 4: 129
  • 2 Kroutil W, Fischereder E.-M, Fuchs CS, Lechner H, Mutti FG, Pressnitz D, Rajagopalan A, Sattler JH, Simon RC, Siirola E. Org. Process Res. Dev. 2013; 17: 751
  • 3 Mathew S, Yun H. ACS Catal. 2012; 2: 993
  • 4 Malik MS, Park E.-S, Shin J.-S. Appl. Microbiol. Biotechnol. 2012; 94: 1163
  • 5 Tufvesson P, Lima-Ramos J, Jensen JS, Al-Haque N, Neto W, Woodley JM. Biotechnol. Bioeng. 2011; 108: 1479
  • 6 Ward J, Wohlgemuth R. Curr. Org. Chem. 2010; 14: 1914
  • 7 Koszelewski D, Tauber K, Faber K, Kroutil W. Trends Biotechnol. 2010; 28: 324
  • 8 Hailes HC, Dalby PA, Lye GJ, Baganz F, Micheletti M, Szita N, Ward JM. Curr. Org. Chem. 2010; 14: 1883
  • 9 Turner NJ, Truppo MD, Chiral Amine Synthesis: Methods, Developments and Applications Nugent TC. Wiley-VCH Weinheim, Germany 2010; 431
  • 10 Turner NJ. Curr. Opin. Chem. Biol. 2010; 14: 115
  • 11 Höhne M, Bornscheuer UT. ChemCatChem 2009; 1: 42
  • 12 Zhu D, Hua L. Biotechnol. J. 2009; 4: 1420
  • 13 Park E.-S, Malik MS, Dong J.-Y, Shin J.-S. ChemCatChem 2013; 5: 1734
  • 14 Fesko K, Steiner K, Breinbauer R, Schwab H, Schürmann M, Strohmeier GA. J. Mol. Catal. B: Enzym. 2013; 96: 103
  • 15 Shin J.-S, Kim B.-G. Biotechnol. Bioeng. 1999; 65: 206
  • 16 Savile CK, Janey JM, Mundorff EC, Moore JC, Tam S, Javis WR, Colbeck JC, Krebber A, Fleitz FJ, Brands J, Devine PN, Huisman GW, Hughes GJ. Science (Washington, D. C.) 2010; 329: 305
  • 17 Truppo MD, Rozzell JD, Moore JC, Turner NJ. Org. Biomol. Chem. 2009; 7: 395
  • 18 Stirling DI, Zeitlin AL, Matcham GW. EP 404 146, 1990 Chem. Abstr.. 1991 114 41055
  • 19 Koszelewski D, Lavandera I, Clay D, Rozzell D, Kroutil W. Adv. Synth. Catal. 2008; 350: 2761
  • 20 Koszelewski D, Clay D, Rozzell D, Kroutil W. Eur. J. Org. Chem. 2009; 2289
  • 21 Koszelewski D, Pressnitz D, Clay D, Kroutil W. Org. Lett. 2009; 11: 4810
  • 22 Mutti FG, Fuchs CS, Pressnitz D, Sattler JH, Kroutil W. Adv. Synth. Catal. 2011; 353: 3227
  • 23 Mutti FG, Fuchs CS, Pressnitz D, Turrini NG, Sattler JH, Lerchner A, Skerra A, Kroutil W. Eur. J. Org. Chem. 2012; 1003
  • 24 Pressnitz D, Fuchs CS, Sattler JH, Knaus T, Macheroux P, Mutti FG, Kroutil W. ACS Catal. 2013; 3: 555
  • 25 Pollard DJ, Woodley JM. Trends Biotechnol. 2007; 25: 66
  • 26 Truppo MD, Rozzell JD, Turner NJ. Org. Process Res. Dev. 2010; 14: 234
  • 27 Emre M. CNS Drugs 2006; 20: 748
  • 28 Park E, Kim M, Shin J.-S. Adv. Synth. Catal. 2010; 352: 3391
  • 29 Fuchs M, Koszelewski D, Tauber K, Sattler J, Banko W, Holzer AK, Pickl M, Kroutil W, Faber K. Tetrahedron 2012; 68: 7691
  • 30 Fuchs M, Koszelewski D, Tauber K, Kroutil W, Faber K. Chem. Commun. (Cambridge) 2010; 46: 5500
  • 31 Girardin M, Ouellet SG, Gauvreau D, Moore JC, Hughes G, Devine PN, OʼShea PD, Campeau L.-C. Org. Process Res. Dev. 2013; 17: 61
  • 32 Koszelewski D, Lavandera I, Clay D, Guebitz GM, Rozzell D, Kroutil W. Angew. Chem. Int. Ed. 2008; 47: 9337
  • 33 Koszelewski D, Göritzer M, Clay D, Seisser B, Kroutil W. ChemCatChem 2010; 2: 73
  • 34 Matcham G, Bhatia M, Lang W, Lewis C, Nelson N, Wang A, Wu W. Chimia 1999; 53: 584
  • 35 Cassimjee KE, Branneby C, Abedi V, Wells A, Berglund P. Chem. Commun. (Cambridge) 2010; 46: 5569
  • 36 Mutti FG, Sattler J, Tauber K, Kroutil W. ChemCatChem 2011; 3: 109
  • 37 Cuetos A, Lavandera I, Gotor V. Chem. Commun. (Cambridge) 2013; 49: 10688
  • 38 Mangion IK, Sherry BD, Yin J, Fleitz FJ. Org. Lett. 2012; 14: 3458
  • 39 Park E.-S, Dong J.-Y, Shin J.-S. Org. Biomol. Chem. 2013; 11: 6929
  • 40 Bea H.-S, Lee S.-H, Yun H. Biotechnol. Bioprocess Eng. 2011; 16: 291
  • 41 Meadows RE, Mulholland KR, Schürmann M, Golden M, Kierkels H, Meulenbroeks E, Mink D, May O, Squire C, Straatman H, Wells AS. Org. Process Res. Dev. 2013; 17: 1117
  • 42 Mutti FG, Kroutil W. Adv. Synth. Catal. 2012; 354: 3409
  • 43 Simon RC, Fuchs CS, Lechner H, Zepeck F, Kroutil W. Eur. J. Org. Chem. 2013; 3397
  • 44 Simon RC, Grischek B, Zepeck F, Steinreiber A, Belaj F, Kroutil W. Angew. Chem. Int. Ed. 2012; 51: 6713
  • 45 Simon RC, Zepeck F, Kroutil W. Chem.–Eur. J. 2013; 19: 2859
  • 46 Bates RW, Sa-Ei K. Tetrahedron 2002; 58: 5957
  • 47 Bailey PD, Millwood PA, Smith PD. Chem. Commun. (Cambridge) 1998; 633
  • 48 Buffat MGP. Tetrahedron 2004; 60: 1701
  • 49 Girling PR, Kiyoi T, Whiting A. Org. Biomol. Chem. 2011; 9: 3105
  • 50 Maruoka K, Miyazaki T, Ando M, Matsumura Y, Sakane S, Hattori K, Yamamoto H. J. Am. Chem. Soc. 1983; 105: 2831
  • 51 Maruoka K, Yamamoto H. Angew. Chem. Int. Ed. Engl. 1985; 24: 668
  • 52 Kaulmann U, Smithies K, Smith MEB, Hailes HC, Ward JM. Enzyme Microb. Technol. 2007; 41: 628
  • 53 Siirola E, Mutti FG, Grischek B, Hoefler SF, Fabian WMF, Grogan G, Kroutil W. Adv. Synth. Catal. 2013; 355: 1703
  • 54 Shin J.-S, Kim B.-G. Biosci., Biotechnol., Biochem. 2001; 65: 1782
  • 55 Martin AR, DiSanto R, Plotnikov I, Kamat S, Shonnard D, Pannuri S. Biochem. Eng. J. 2007; 37: 246
  • 56 Jiang J, Chen X, Feng J, Wu Q, Zhu D. J. Mol. Catal. B: Enzym. 2014; 100: 32
  • 57 Cho B.-K, Park H.-Y, Seo J.-H, Kim J, Kang T.-J, Lee B.-S, Kim B.-G. Biotechnol. Bioeng. 2008; 99: 275
  • 58 Busto E, Simon RC, Grischek B, Gotor-Fernández V, Kroutil W. Adv. Synth. Catal. 2014; 356: 1937
  • 59 Busto E, Gotor-Fernández V, Gotor V. J. Org. Chem. 2012; 77: 4842
  • 60 Molinaro C, Bulger PG, Lee EE, Kosjek B, Lau S, Gauvreau D, Howard ME, Wallace DJ, OʼShea PD. J. Org. Chem. 2012; 77: 2299
  • 61 Mack DJ, Weinrich ML, Vitaku E, Njarðarson JT Top 200 Brand Name Drugs by Total US Prescriptions in 2010; http://cbc.arizona.edu/njardarson/group/top-pharmaceuticals-poster (accessed June 2014
  • 62 Austad B, Bahadoor A, Belani JD, Janardanannair S, Johannes CW, Keaney GF, Lo CK, Wallerstein SL. WO 2011 017 551, 2011 Chem. Abstr.. 2011 154 234910
  • 63 Geisler J, Sasano H, Chen SA, Purohit A. J. Steroid Biochem. Mol. Biol. 2011; 125: 39
  • 64 Maltais R, Poirier D. Steroids 2011; 76: 929
  • 65 Mostafa YA, Taylor SD. Bioorg. Med. Chem. 2012; 20: 1535
  • 66 Taylor SD, Harris J. Steroids 2011; 76: 1098
  • 67 Richter N, Simon RC, Kroutil W, Ward JM, Hailes HC. Chem. Commun. (Cambridge) 2014; 50: 6098
  • 68 Yun H, Lim S, Cho B.-K, Kim B.-G. Appl. Environ. Microbiol. 2004; 70: 2529
  • 69 Shin J.-S, Yun H, Jang J.-W, Park I, Kim B.-G. Appl. Microbiol. Biotechnol. 2003; 61: 463
  • 70 Kim J, Kyung D, Yun H, Cho B.-K, Seo J.-H, Cha M, Kim B.-G. Appl. Environ. Microbiol. 2007; 73: 1772
  • 71 Shin J.-S, Kim B.-G. J. Org. Chem. 2002; 67: 2848
  • 72 GABA-Neurotransmitters: Pharmacochemical, Biochemical and Pharmacological Aspects. Krogsgaard-Larsen P, Scheel-Krüger J, Kofod H. Munksgaard; Copenhagen 1979
  • 73 Koszelewski D, Clay D, Faber K, Kroutil W. J. Mol. Catal. B: Enzym. 2009; 60: 191
  • 74 Bähn S, Imm S, Neubert L, Zhang M, Neumann H, Beller M. ChemCatChem 2011; 3: 1853
  • 75 Guillena G, Ramón DJ, Yus M. Chem. Rev. 2010; 110: 1611
  • 76 Sattler JH, Fuchs M, Tauber K, Mutti FG, Faber K, Pfeffer J, Haas T, Kroutil W. Angew. Chem. Int. Ed. 2012; 51: 9156
  • 77 Fuchs M, Tauber K, Sattler J, Lechner H, Pfeffer J, Kroutil W, Faber K. RSC Adv. 2012; 2: 6262
  • 78 Tauber K, Fuchs M, Sattler JH, Pitzer J, Pressnitz D, Koszelewski D, Faber K, Pfeffer J, Haas T, Kroutil W. Chem.–Eur. J. 2013; 19: 4030
  • 79 Lerchner A, Achatz S, Rausch C, Haas T, Skerra A. ChemCatChem 2013; 5: 3374
  • 80 Allen AJ, Kelsey DK. WO 2005 020 976, 2005 Chem. Abstr.. 2005 142 291415
  • 81 Beadle CD, Cases-Thomas MJ, Clark BP, Gallagher PT, Masters JJ, Timms GH, Walter MW, Whatton MA, Wood VA, Gilmore J. WO 2005 000 811, 2005 Chem. Abstr.. 2005 142 113884
  • 82 Muller M, Soukup M. WO 2004 013 097, 2004 Chem. Abstr.. 2004 140 163625
  • 83 Rowbottom MW, Vickers TD, Dyck B, Grey J, Tamiya J, Zhang M, Kiankarimi M, Wu D, Dwight W, Wade WS, Schwarz D, Heise CE, Madan A, Fisher A, Petroski R, Goodfellow VS. Bioorg. Med. Chem. Lett. 2006; 16: 4450
  • 84 Sanchez JP, Domagala JM, Heifetz CL, Priebe SR, Sesnie JA, Trehan AK. J. Med. Chem. 1992; 35: 1764
  • 85 Höhne M, Robins K, Bornscheuer UT. Adv. Synth. Catal. 2008; 350: 807
  • 86 Koszelewski D, Müller N, Schrittwieser JH, Faber K, Kroutil W. J. Mol. Catal. B: Enzym. 2010; 63: 39
  • 87 Shin G, Mathew S, Shon M, Kim B.-G, Yun H. Chem. Commun. (Cambridge) 2013; 49: 8629