PDF herunterladen
Faber, K. et al.: 2015 Science of Synthesis: Biocatalysis Organic Synthesis 2 DOI: 10.1055/sos-SD-215-00272
Biocatalysis in Organic Synthesis 2

2.6.1 Asymmetric Synthesis of Enantiopure Epoxides Using Monooxygenases

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

1st edition © 2015. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: Organische Chemie

Science of Synthesis Reference Libraries



Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Typ: Mehrbändiges Werk

Auch verfügbar auf
 


Abstract

Monooxygenases catalyze the asymmetric epoxidation of different types of alkenes, providing a green and useful method to synthesize the corresponding epoxides in high enantiomeric excess and good yield. The epoxidations catalyzed by styrene monooxygenase, xylene monooxygenase, alkane monooxygenase, alkene monooxygenase, and cytochrome P450 monooxygenase are reviewed in this chapter.

Schlüsselwörter

asymmetric epoxidation - asymmetric synthesis - enzyme catalysis - monooxygenase - chiral epoxides - green oxidation
 
  • 1 Farina V, Reeves JT, Senanayake CH, Song JJ. Chem. Rev. 2006; 106: 2734
  • 2 Katsuki T, Sharpless KB. J. Am. Chem. Soc. 1980; 102: 7932
  • 3 Zhang W, Loebach JL, Wilson SR, Jacobsen EN. J. Am. Chem. Soc. 1990; 112: 280
  • 4 Wang Z.-X, Tu Y, Frohn M, Zhang J.-R, Shi Y. J. Am. Chem. Soc. 1997; 119: 11224
  • 5 Tian H, She X, Xu J, Shi Y. Org. Lett. 2001; 3: 1929
  • 6 Collman JP, Wang Z, Straumanis A, Quelquejeu M, Rose E. J. Am. Chem. Soc. 1999; 121: 460
  • 7 Li Z, van Beilen JB, Duetz WA, Schmid A, de Raadt A, Griengl H, Witholt B. Curr. Opin. Chem. Biol. 2002; 6: 136
  • 8 Besse P, Veschambre H. Tetrahedron 1994; 50: 8885
  • 9 Martinez CA, Stewart JD. Curr. Org. Chem. 2000; 4: 263
  • 10 Chang D, Zhang J, Witholt B, Li Z. Biocatal. Biotransform. 2004; 22: 113
  • 11 Hwang S, Choi CY, Lee EY. J. Ind. Eng. Chem. (Amsterdam, Neth.) 2010; 16: 1
  • 12 Lin H, Liu J.-Y, Wang H.-B, Qaed Ahmed AA, Wu Z.-L. J. Mol. Catal. B: Enzym. 2011; 72: 77
  • 13 Panke S, Witholt B, Schmid A, Wubbolts MG. Appl. Environ. Microbiol. 1998; 64: 2032
  • 14 Mooney A, Ward P, OʼConnor KE. Appl. Microbiol. Biotechnol. 2006; 72: 1
  • 15 Kantz A, Chin F, Nallamothu N, Nguyen T, Gassner GT. Arch. Biochem. Biophys. 2005; 442: 102
  • 16 Otto K, Hofstetter K, Röthlisberger M, Witholt B, Schmid A. J. Bacteriol. 2004; 186: 5292
  • 17 Kantz A, Gassner GT. Biochemistry 2011; 50: 523
  • 18 Ukaegbu UE, Kantz A, Beaton M, Gassner GT, Rosenzweig AC. Biochemistry 2010; 49: 1678
  • 19 Kantz AA, Lam S, Nguyen M, Nguyen T, Gassner G. FASEB J. 2006; 20: A892
  • 20 Panke S, Wubbolts MG, Schmid A, Witholt B. Biotechnol. Bioeng. 2000; 69: 91
  • 21 Park J.-B, Bühler B, Habicher T, Hauer B, Panke S, Witholt B, Schmid A. Biotechnol. Bioeng. 2006; 95: 501
  • 22 Schmid A, Hofstetter K, Feiten H.-J, Hollmann F, Witholt B. Adv. Synth. Catal. 2001; 343: 732
  • 23 Panke S, Held M, Wubbolts MG, Witholt B, Schmid A. Biotechnol. Bioeng. 2002; 80: 33
  • 24 Kuhn D, Abdul Kholiq M, Heinzle E, Bühler B, Schmid A. Green Chem. 2010; 12: 815
  • 25 Hollmann F, Lin P.-C, Witholt B, Schmid A. J. Am. Chem. Soc. 2003; 125: 8209
  • 26 Di Gennaro P, Colmegna A, Galli E, Sello G, Pelizzoni F, Bestetti G. Appl. Environ. Microbiol. 1999; 65: 2794
  • 27 Bernasconi S, Orsini F, Sello G, Colmegna A, Galli E, Bestetti G. Tetrahedron Lett. 2000; 41: 9157
  • 28 Bernasconi S, Orsini F, Sello G, Di Gennaro P. Tetrahedron: Asymmetry 2004; 15: 1603
  • 29 Park MS, Han JH, Yoo SS, Lee EY, Lee SG, Park S. Korean J. Chem. Eng. 2005; 22: 418
  • 30 Lin H, Qiao J, Liu Y, Wu Z.-L. J. Mol. Catal. B: Enzym. 2010; 67: 236
  • 31 Lin H, Liu Y, Wu Z.-L. Tetrahedron: Asymmetry 2011; 22: 134
  • 32 Toda H, Itoh N. J. Biosci. Bioeng. 2012; 113: 12
  • 33 Toda H, Imae R, Komio T, Itoh N. Appl. Microbiol. Biotechnol. 2012; 96: 407
  • 34 Toda H, Imae R, Komio T, Itoh N. Tetrahedron: Asymmetry 2012; 23: 1542
  • 35 Tischler D, Eulberg D, Lakner S, Kaschabek SR, van Berkel WJH, Schlömann M. J. Bacteriol. 2009; 191: 4996
  • 36 Tischler D, Kermer R, Gröning JAD, Kaschabek SR, van Berkel WJH, Schlömann M. J. Bacteriol. 2010; 192: 5220
  • 37 van Hellemond EW, Janssen DB, Fraaije MW. Appl. Environ. Microbiol. 2007; 73: 5832
  • 38 Panke S, Meyer A, Huber CM, Witholt B, Wubbolts MG. Appl. Environ. Microbiol. 1999; 65: 2324
  • 39 Riesenberg D, Schulz V, Knorre WA, Pohl H.-D, Korz D, Sanders EA, Roß A, Deckwer W.-D. J. Biotechnol. 1991; 20: 17
  • 40 Qaed AA, Lin H, Tang D.-F, Wu Z.-L. Biotechnol. Lett. 2011; 33: 611
  • 41 Patel RN. Coord. Chem. Rev. 2008; 252: 659
  • 42 Lin H, Tang D.-F, Qaed Ahmed AA, Liu Y, Wu Z.-L. J. Biotechnol. 2012; 161: 235
  • 43 Gursky LJ, Nikodinovic-Runic J, Feenstra KA, OʼConnor KE. Appl. Microbiol. Biotechnol. 2010; 85: 995
  • 44 Lin H, Liu Y, Wu Z.-L. Chem. Commun. (Cambridge) 2011; 47: 2610
  • 45 Jung ME, Jung YH. Tetrahedron Lett. 1989; 30: 6637
  • 46 Zhang W, Basak A, Kosugi Y, Hoshino Y, Yamamoto H. Angew. Chem. Int. Ed. 2005; 44: 4389
  • 47 Austin RN, Buzzi K, Kim E, Zylstra GJ, Groves JT. JBIC, J. Biol. Inorg. Chem. 2003; 8: 733
  • 48 Wubbolts MG, Noordman R, van Beilen JB, Witholt B. Recl. Trav. Chim. Pays-Bas 1995; 114: 139
  • 49 Wubbolts MG, Reuvekamp P, Witholt B. Enzyme Microb. Technol. 1994; 16: 608
  • 50 Harayama S, Rekik M, Wubbolts M, Rose KRA, Timmis KN. J. Bacteriol. 1989; 171: 5048
  • 51 Suzuki M, Hayakawa T, Shaw JP, Rekik M, Harayama S. J. Bacteriol. 1991; 173: 1690
  • 52 Shaw JP, Harayama S. J. Ferment. Bioeng. 1995; 79: 195
  • 53 Shaw JP, Harayama S. Eur. J. Biochem. 1992; 209: 51
  • 54 Wubbolts MG, Hoven J, Melgert B, Witholt B. Enzyme Microb. Technol. 1994; 16: 887
  • 55 Panke S, de Lorenzo V, Kaiser A, Witholt B. Appl. Environ. Microbiol. 1999; 65: 5619
  • 56 van Beilen JB, Wubbolts MG, Witholt B. Biodegradation 1994; 5: 161
  • 57 Grund A, Shapiro J, Fennewald M, Bacha P, Leahy J, Markbreiter K, Nieder M, Toepfer M. J. Bacteriol. 1975; 123: 546
  • 58 Eggink G, Engel H, Meijer WG, Otten J, Kingma J, Witholt B. J. Biol. Chem. 1988; 263: 13400
  • 59 Sticher P, Jaspers MCM, Stemmler K, Harms H, Zehnder AJB, van der Meer JR. Appl. Environ. Microbiol. 1997; 63: 4053
  • 60 Favre-Bulle O, Witholt B. Enzyme Microb. Technol. 1992; 14: 931
  • 61 Peterson JA, Kusunose M, Kusunose E, Coon MJ. J. Biol. Chem. 1967; 242: 4334
  • 62 McKenna EJ, Coon MJ. J. Biol. Chem. 1970; 245: 3882
  • 63 Kok M, Oldenhuis R, van der Linden MPG, Raatjes P, Kingma J, van Lelyveld PH, Witholt B. J. Biol. Chem. 1989; 264: 5435
  • 64 Staijen IE, Hatzimanikatis V, Witholt B. Eur. J. Biochem. 1997; 244: 462
  • 65 May SW, Steltenkamp MS, Schwartz RD, McCoy CJ. J. Am. Chem. Soc. 1976; 98: 7856
  • 66 De Smet MJ, Witholt B, Wynberg H. J. Org. Chem. 1981; 46: 3128
  • 67 De Smet MJ, Kingma J, Wynberg H, Witholt B. Enzyme Microb. Technol. 1983; 5: 352
  • 68 Lageveen RG, Huisman GW, Preusting H. Appl. Environ. Microbiol. 1988; 54: 2924
  • 69 Fu H, Newcomb M, Wong C.-H. J. Am. Chem. Soc. 1991; 113: 5878
  • 70 Fu H, Shen GJ, Wong C.-H. Recl. Trav. Chim. Pays-Bas 1991; 110: 167
  • 71 Miyano S, Lu LDL, Viti SM, Sharpless KB. J. Org. Chem. 1985; 50: 4350
  • 72 Pederson RL, Liu KK.-C, Rutan JF, Chen L, Wong C.-H. J. Org. Chem. 1990; 55: 4897
  • 73 Gallagher SC, Cammack R, Dalton H. Eur. J. Biochem. 1997; 247: 635
  • 74 Small FJ, Ensign SA. J. Biol. Chem. 1997; 272: 24913
  • 75 Miura A, Dalton H. Biosci., Biotechnol., Biochem. 1995; 59: 853
  • 76 Gallagher SC, Cammack R, Dalton H. Biochem. J. 1999; 339: 79
  • 77 Gallagher SC, George A, Dalton H. Eur. J. Biochem. 1998; 254: 480
  • 78 Chion CKCK, Askew SE, Leak DJ. Appl. Environ. Microbiol. 2005; 71: 1909
  • 79 Ono M, Okura I. J. Mol. Catal. 1990; 61: 113
  • 80 Saeki H, Furuhashi K. J. Ferment. Bioeng. 1994; 78: 399
  • 81 Smith TJ, Lloyd JS, Gallagher SC, Fosdike WLJ, Murrell JC, Dalton H. Eur. J. Biochem. 1999; 260: 446
  • 82 Habets-Crützen AQH, Carlier SJN, de Bont JAM, Wistuba D, Schurig V, Hartmans S, Tramper J. Enzyme Microb. Technol. 1985; 7: 17
  • 83 Weijers CAGM, van Ginkel CG, de Bont JAM. Enzyme Microb. Technol. 1988; 10: 214
  • 84 Peterson JA, Graham SE. Structure (Oxford, U. K.) 1998; 6: 1079
  • 85 Nebert DW, Gonzalez FJ. Annu. Rev. Biochem. 1987; 56: 945
  • 86 Matson RS, Hare RS, Fulco AJ. Biochim. Biophys. Acta 1977; 487: 487
  • 87 Munro AW, Noble MA, Ost TW, Green AJ, McLean KJ, Robledo L, Miles CS, Murdoch J, Chapman SK. Subcell. Biochem. 2000; 35: 297
  • 88 Narhi LO, Fulco AJ. J. Biol. Chem. 1986; 261: 7160
  • 89 Roberts GA, Grogan G, Greter A, Flitsch SL, Turner NJ. J. Bacteriol. 2002; 184: 3898
  • 90 Farinas ET, Alcalde M, Arnold FH. Tetrahedron 2004; 60: 525
  • 91 Nickerson DP, Harford-Cross CF, Fulcher SR, Wong L. FEBS Lett. 1997; 405: 153
  • 92 Vaz ADN, McGinnity DF, Coon MJ. Proc. Natl. Acad. Sci. U. S. A. 1998; 95: 3555
  • 93 Fruetel JA, Mackman RL, Peterson JA, Ortiz de Montellano PR. J. Biol. Chem. 1994; 269: 28815
  • 94 Li AT, Wu SK, Adams JP, Snajdrova R, Li Z. Chem. Commun. (Cambridge) 2014; 50: 8771
  • 95 Schallmey A, den Besten G, Teune IGP, Kembaren RF, Janssen DB. Appl. Microbiol. Biotechnol. 2011; 89: 1475
  • 96 Li AT, Liu J, Pham SQ, Li Z. Chem. Commun. (Cambridge) 2013; 49: 11572
  • 97 Bellucci G, Chiappe C, Cordoni A, Marioni F. Biocatalysis 1994; 10: 149
  • 98 Foreman GL, Harris C, Guengerich FP, Bend JR. J. Pharmacol. Exp. Ther. 1989; 248: 492
  • 99 Eiben S, Kaysser L, Maurer S, Kühnel K, Urlacher VB, Schmid RD. J. Biotechnol. 2006; 124: 662
  • 100 Li QS, Ogawa J, Schmid RD, Shimizu S. FEBS Lett. 2001; 508: 249
  • 101 Kubo T, Peters MW, Meinhold P, Arnold FH. Chem.–Eur. J. 2006; 12: 1216
  • 102 Chiappe C, De Rubertis A, Amato G, Gervasi PG. Chem. Res. Toxicol. 1998; 11: 1487
  • 103 Wistuba D, Novotny H.-P, Träger O, Shurig V. Chirality 1989; 1: 127
  • 104 Shurig V, Wistuba D. Angew. Chem. Int. Ed. Engl. 1984; 23: 796
  • 105 Gelb MH, Malkonen P, Sligar S. Biochem. Biophys. Res. Commun. 1982; 104: 853
  • 106 Maryniak DM, Kadkhodayan S, Crull GB, Bryson TA, Dawson JH. Tetrahedron 1993; 49: 9373
  • 107 van Bladeren PJ, Vyas KP, Sayer JM, Ryan DE, Thomas PE, Levin W, Jerina DM. J. Biol. Chem. 1984; 259: 8966
  • 108 van Bladeren PJ, Armstrong RN, Cobb D, Thakker DR, Ryan DE, Thomas PE, Sharma ND, Boyd DR, Levin W, Jerina DM. Biochem. Biophys. Res. Commun. 1982; 106: 602
  • 109 Balani SK, Yeh HJC, Ryan DE, Thomas PE, Levin W, Jerina DM. Biochem. Biophys. Res. Commun. 1985; 130: 610
  • 110 Armstrong RN, Levin W, Ryan DE, Thomas PE, Mah HD, Jerina DM. Biochem. Biophys. Res. Commun. 1981; 100: 1077
  • 111 Ho PP, Fulco AJ. Biochim. Biophys. Acta 1976; 431: 249
  • 112 Fulco AJ. Annu. Rev. Pharmacol. Toxicol. 1991; 31: 177
  • 113 Kato T, Yamaguchi Y, Hirano T, Yokoyama T, Uyehara T, Namai T, Yamanaka S, Harada N. Chem. Lett. 1984; 13: 409
  • 114 Stimers JR, Dobretsov M, Hastings SL, Jude AR, Grant DF. Biochim. Biophys. Acta 1999; 1438: 359
  • 115 Ishizaki T, Ozawa T, Voelkel NF. Pulm. Pharmacol. Ther. 1999; 12: 145
  • 116 Kosaka K, Suzuki K, Hayakawa M, Sugiyama S, Ozawa T. Mol. Cell. Biochem. 1994; 139: 141
  • 117 Sugiyama S, Hayakawa M, Hanaki Y, Hieda N, Asai J, Ozawa T. Life Sci. 1988; 43: 221
  • 118 Çelik A, Sperandio D, Speight RE, Turner NJ. Org. Biomol. Chem. 2005; 3: 2688
  • 119 Capdevila JH, Wei S, Helvig C, Falck JR, Belosludtsev Y, Truan G, Graham-Lorence SE, Peterson JA. J. Biol. Chem. 1996; 271: 22663
  • 120 Graham-Lorence S, Truan G, Peterson JA, Falck JR, Wei S, Helvig C, Capdevila JH. J. Biol. Chem. 1997; 272: 1127
  • 121 Falck JR, Reddy YK, Haines DC, Reddy KM, Krishna UM, Graham S, Murry B, Peterson JA. Tetrahedron Lett. 2001; 42: 4131