Stereocontrol strategies in the asymmetric bioreduction of alkenes

Synlett

Volumn 23, Issue 13, 2012, Pages 1857-1864

  Oberdorfer, Gustav ^a,b   Gruber, Karl ^b   Faber, Kurt ^c   Hall, Mélanie ^c  

^a AUSTRIAN CENTRE OF INDUSTRIAL BIOTECHNOLOGY   (Austria)

^b Institute of Molecular Biosciences   (Austria)

^c UNIVERSITY OF GRAZ   (Austria)

Author keywords

asymmetric alkene reduction; biocatalysis; ene reductase; Old Yellow Enzyme; stereocontrol

Indexed keywords

ALKENE; ISOENZYME; OXIDOREDUCTASE;

ARTICLE; ASYMMETRIC BIOREDUCTION; BINDING AFFINITY; BIOCATALYSIS; CHEMICAL PHENOMENA; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ENZYME ACTIVE SITE; ENZYME SUBSTRATE COMPLEX; MOLECULAR DOCKING; MOLECULAR MODEL; MOLECULAR SIZE; NONHUMAN; PREDICTION; STEREOCHEMISTRY; STEREOCONTROL; STEREOSPECIFICITY;

EID: 84863891471     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1316591     Document Type: Article

References (34)

1. Faber K. Biotransformations in Organic Chemistry. 6th ed. Springer Heidelberg: 2011
2. Mugford PF, Wagner UG, Jiang Y, Faber K, Kazlauskas RJ. Angew. Chem. Int. Ed.: 2008; 47 8782
3. Derewenda ZS, Wei Y. J. Am. Chem. Soc.: 1995; 117 2104
4. Kazlauskas RJ, Weissfloch AN. E. J. Mol. Catal. B: Enzym.: 1997; 3 65
5. Mugford P, Wagner U, Jiang Y, Faber K, Kazlauskas RJ. Angew. Chem. Int. Ed.: 2008; 47 8782
6. Dashipour M, Asano Y. ACS Catal.: 2011; 1 1121
7. Purkarthofer T, Scranc W, Schuster C, Griengl H. Appl. Microbiol. Biotechnol.: 2007; 76 309
8. Gruber K, Kratky C. J. Polym. Sci. A: Polym. Chem.: 2004; 42 479
9. Gregory RJ. H. Chem. Rev.: 1999; 99 3649
10. Griengl H, Schwab H, Fechter M. Trends Biotechnol.: 2000; 18 252
11. Kallwass HK. W. Enzyme Microb. Technol.: 1992; 14 28
12. Hummel W, Schütte H, Kula M.-R. Appl. Microbiol. Biotechnol.: 1985; 21 7
13. Schütte H, Hummel W, Kula M.-R. Appl. Microbiol. Biotechnol.: 1984; 19 167
14. Yennawar NH, Conway ME, Yennawar HP, Farber GK, Hutson SM. Biochemistry: 2002; 41 11592
15. Davoodi J, Drown PM, Bledsoe RK, Wallin R, Reinhart GD, Hutson SM. J. Biol. Chem.: 1998; 273 4982
16. Parales RE, Resnick SM, Yu C, Boyd DR, Sharma ND, Gibson DT. J. Bacteriol.: 2000; 182 5495
17. Li Y, Aubert SD, Maes EG, Raushel FM. J. Am. Chem. Soc.: 2004; 126 8888
18. Ozaki S.-I, Ortiz de Montellano PR. J. Am. Chem. Soc.: 1994; 116 4487
19. Savenkova MI, Newmyer SL, Ortiz de Montellano PR. J. Biol. Chem.: 1996; 271 24598
20. Bartsch S, Kourist R, Bornscheuer UT. Angew. Chem. Int. Ed.: 2008; 47 1508
21. Terao Y, Ijima Y, Miyamoto K, Ohta H. J. Mol. Catal. B: Enzym.: 2007; 45 15
22. Adachi K, Kobayashi S, Ohno M. Chimia: 1986; 40 311
23. Winkler CK, Stueckler C, Mueller NJ, Pressnitz D, Faber K. Eur. J. Org. Chem.: 2010; 6354
24. Stueckler C, Winkler CK, Hall M, Hauer B, Bonnekessel M, Zangger K, Faber K. Adv. Synth. Catal.: 2011; 353 1169
25. Chen C.-S, Sih CJ. Angew. Chem.: 1989; 101 711
26. Faber K, Ottolina G, Riva S. Biocatalysis: 1993; 8 91
27. 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
28. Oberdorfer G, Steinkellner G, Stückler C, Faber K, Gruber K. ChemCatChem: 2011; 3 1562
29. Jorgensen WL, Maxwell DS, Tirado-Rives J. J. Am. Chem. Soc.: 1996; 118 11225
30. Jorgensen WL, Tirado-Rives J. J. Am. Chem. Soc.: 1988; 110 1657
31. Fiser A, Kinh Gian Do R, Sali A. Prot. Sci.: 2000; 9 1753
32. Sali A, Blundell TL. J. Mol. Biol.: 1993; 234 779
33. Krieger E, Darden T, Nabuurs SB, Finkelstein A, Vriend G. Proteins: Struct. Funct. Bioinf.: 2004; 57 678
34. Krieger E, Koraimann G, Vriend G. Proteins: Struct. Funct. Genet.: 2002; 47 393