2.3. 1 Addition of Hydrogen to C=C Bonds: Alkene Reduction
Book
Editors: Faber, K.; Fessner, W.-D.; Turner, N. J.
Title: Biocatalysis Organic Synthesis 2
Print ISBN: 9783131741615; Online ISBN: 9783131975317; Book DOI: 10.1055/b-003-125813
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
Abstract
Ene-reductases are flavoproteins which catalyze the asymmetric reduction of activated alkenes at the expense of a nicotinamide cofactor. The substrate scope is broad and includes α, β-unsaturated carbonyl compounds, carboxylic acid derivatives, and nitro compounds, which upon reduction yield the corresponding saturated products in high enantiopurity.
Key words
asymmetric catalysis - ene reaction - enzyme catalysis - reduction - stereoselective synthesis- 7 Hall M, Yanto Y, Bommarius AS, Encyclopedia of Industrial Biotechnology: Bioprocess, Bioseparation, and Cell Technology. Flickinger MC. Wiley; Hoboken, NJ 2010: 2234
- 12 Chaparro-Riggers JF, Rogers TA, Vazquez-Figueroa E, Polizzi KM, Bommarius AS. Adv. Synth. Catal. 2007; 349: 1521
- 13 Kataoka M, Kotaka A, Hasegawa A, Wada M, Yoshizumi A, Nakamori S, Shimizu S. Biosci., Biotechnol., Biochem. 2002; 66: 2651
- 23 Adalbjörnsson BV, Toogood HS, Fryszkowska A, Pudney CR, Jowitt TA, Leys D, Scrutton NS. ChemBioChem 2010; 11: 197
- 24 Schittmayer M, Glieder A, Uhl MK, Winkler A, Zach S, Schrittwieser JH, Kroutil W, Macheroux P, Gruber K, Kambourakis S, Rozzell JD, Winkler M. Adv. Synth. Catal. 2011; 353: 268
- 27 Opperman DJ, Sewell BT, Litthauer D, Isupov MN, Littlechild JA, van Heerden E. Biochem. Biophys. Res. Commun. 2010; 393: 426
- 31 Miura K, Tomioka Y, Suzuki H, Yonezawa M, Hishinuma T, Mizugaki M. Biol. Pharm. Bull. 1997; 20: 110
- 33 Straßner J, Schaller F, Frick UB, Howe GA, Weiler EW, Amrhein N, Macheroux P, Schaller A. Plant J. 2002; 32: 585
- 34 Tischer W, Bühler M, Sedlmaier H, Schmidtchen F, Simon H. Hoppe–Seylerʼs Z. Physiol. Chem. 1978; 359: 1157
- 35 Caldeira J, Feicht R, White H, Teixeira M, Moura JJG, Simon H, Moura I. J. Biol. Chem. 1996; 271: 18743
- 37 Hall M, Stueckler C, Ehammer H, Pointner E, Oberdorfer G, Gruber K, Hauer B, Stuermer R, Kroutil W, Macheroux P, Faber K. Adv. Synth. Catal. 2008; 350: 411
- 38 Hall M, Stueckler C, Hauer B, Stuermer R, Friedrich T, Breuer M, Kroutil W, Faber K. Eur. J. Org. Chem. 2008; 1511
- 40 Paul CE, Gargiulo S, Opperman DJ, Lavandera I, Gotor-Fernández V, Gotor V, Taglieber A, Arends IWCE, Hollmann F. Org. Lett. 2013; 15: 180
- 41 Hulley ME, Toogood HS, Fryszkowska A, Mansell D, Stephens GM, Gardiner JM, Scrutton NS. ChemBioChem 2010; 11: 2433
- 42 Mansell DJ, Toogood HS, Waller J, Hughes JMX, Levy CW, Gardiner JM, Scrutton NS. ACS Catal. 2013; 3: 370
- 43 Stueckler C, Mueller NJ, Winkler CK, Glueck SM, Gruber K, Steinkellner G, Faber K. Dalton Trans. 2010; 39: 8472
- 45 Brenna E, Cosi SL, Ferrandi EE, Gatti FG, Monti D, Parmeggiani F, Sacchetti A. Org. Biomol. Chem. 2013; 11: 2988
- 53 Stueckler C, Hall M, Ehammer H, Pointner E, Kroutil W, Macheroux P, Faber K. Org. Lett. 2007; 9: 5409
- 61 Stueckler C, Winkler CK, Hall M, Hauer B, Bonnekessel M, Zangger K, Faber K. Adv. Synth. Catal. 2011; 353: 1169
- 62 Tasnádi G, Winkler CK, Clay D, Sultana N, Fabian WMF, Hall M, Ditrich K, Faber K. Chem.–Eur. J. 2012; 18: 10362
- 63 Brenna E, Crotti M, Gatti FG, Manfredi A, Monti D, Parmeggiani F, Pugliese A, Zampieri D. J. Mol. Catal. B: Enzym. 2014; 101: 67
- 68 Burda E, Reß T, Winkler T, Giese C, Kostrov X, Huber T, Hummel W, Gröger H. Angew. Chem. Int. Ed. 2013; 52: 9323
- 71 Toogood HS, Fryszkowska A, Hare V, Fisher K, Roujeinikova A, Leys D, Gardiner JM, Stephens GM, Scrutton NS. Adv. Synth. Catal. 2008; 350: 2789
- 72 Durchschein K, Wallner S, Macheroux P, Schwab W, Winkler T, Kreis W, Faber K. Eur. J. Org. Chem. 2012; 4963
- 74 Winkler CK, Clay D, Turrini NG, Lechner H, Kroutil W, Davies S, Debarge S, OʼNeill P, Steflik J, Karmilowicz M, Wong JW, Faber K. Adv. Synth. Catal. 2014; 356: 1878
- 79 Winkler CK, Clay D, Davies S, OʼNeill P, McDaid P, Debarge S, Steflik J, Karmilowicz M, Wong JW, Faber K. J. Org. Chem. 2013; 78: 1525
- 80 Fryszkowska A, Toogood H, Sakuma M, Stephens GM, Gardiner JM, Scrutton NS. Catal. Sci. Technol. 2011; 1: 948
- 93 Fisher K, Mohr S, Mansell D, Goddard NJ, Fielden PR, Scrutton NS. Catal. Sci. Technol. 2013; 3: 1505
- 98 Grau MM, van der Toorn JC, Otten LG, Macheroux P, Taglieber A, Zilly FE, Arends IWCE, Hollmann F. Adv. Synth. Catal. 2009; 351: 3279
- 101 Bechtold M, Brenna E, Femmer C, Gatti FG, Panke S, Parmeggiani F, Sacchetti A. Org. Process Res. Dev. 2012; 16: 269
- 102 Debarge S, McDaid P, OʼNeill P, Frahill J, Wong JW, Carr D, Burrell A, Davies S, Karmilowicz M, Steflik J. Org. Process Res. Dev. 2014; 18: 109