Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis

Chemical Communications

Volumn 50, Issue 99, 2014, Pages 15669-15672

  Simon, Robert C ^a   Busto, Eduardo ^a   Schrittwieser, Joerg H ^a   Sattler, Johann H ^b   Pietruszka, Jörg ^c   Faber, Kurt ^a   Kroutil, Wolfgang ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b AUSTRIAN CENTRE OF INDUSTRIAL BIOTECHNOLOGY   (Austria)

^c HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; ALCOHOL DEHYDROGENASE; BUTYROPHENONE DERIVATIVE; KETONE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; NORVALINE; REDUCING AGENT; SOLVENT; VALINE;

ANALOGS AND DERIVATIVES; BINDING SITE; BIOCATALYSIS; BIOSYNTHESIS; CHEMISTRY; METABOLISM; MOLECULAR DOCKING; OXIDATION REDUCTION REACTION; PROTEIN TERTIARY STRUCTURE; STEREOISOMERISM; SYNTHESIS; ARTICLE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; LACTONIZATION; MANNICH REACTION; REACTION TIME; STEREOCHEMISTRY; TRANSESTERIFICATION;

2-PROPANOL; ALCOHOL OXIDOREDUCTASES; BINDING SITES; BIOCATALYSIS; BUTYROPHENONES; KETONES; MOLECULAR DOCKING SIMULATION; NADP; OXIDATION-REDUCTION; PROTEIN STRUCTURE, TERTIARY; REDUCING AGENTS; SOLVENTS; STEREOISOMERISM; VALINE;

EID: 84911471963     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc06230b     Document Type: Article

References (52)

1. R. Noyori, Nat. Chem. 2009, 1, 5
2. Z. Du, Z. Shao, Chem. Soc. Rev. 2013, 42, 1337
3. M. á. Fernández-Ibañez, B. Maciá, D. A. Alonso, I. M. Pastor, Molecules, 2013, 18, 10108
4. L. Stegbauer, F. Sladojevich, D. J. Dixon, Chem. Sci. 2012, 3, 942
5. C. Zhong, X. Shi, Eur. J. Org. Chem. 2010, 2999
6. B. Martín-Matute, J.-E. Bäckvall, Curr. Opin. Chem. Biol. 2007, 11, 226
7. O. Pàmies, J.-E. Bäckvall, Chem. Rev. 2003, 103, 3247
8. H. Gröger, W. Hummel, Curr. Opin. Chem. Biol. 2014, 19, 171
9. K. Baer, M. Kraußer, E. Burda, W. Hummel, A. Berkessel, H. Gröger, Angew. Chem. Int. Ed. 2009, 48, 9355
10. G. Rulli, N. Duangdee, K. Baer, W. Hummel, A. Berkessel, H. Gröger, Angew. Chem. Int. Ed. 2011, 50, 7944
11. G. Rulli, M. Heidlindemann, A. Berkessel, W. Hummel, H. Gröger, J. Biotechnol. 2013, 168, 271
12. M. Heidlindemann, G. Rulli, A. Berkessel, W. Hummel, H. Gröger, ACS Catal. 2014, 4, 1099
13. A. Kinnell, T. Harman, M. Bingham, A. Berry, A. Nelson, Tetrahedron, 2012, 68, 7719
14. R. Millet, A. M. Träff, M. L. Petrus, J.-E. Bäckvall, J. Am. Chem. Soc. 2010, 132, 15182
15. W. Schaper, M. Beckmann, U. Doller, G. Krautstrunk, D. Jans, W. Hempel and J. M. Waibel, US2004/6047 A1, US, 2004
16. J. Nielsen and M. Givskov, WO03106445 (A1), 2003
17. H. Hasegawa, N. Shiori, T. Narita and T. Katori, US4876359 A1, 1989
18. L. Fowden, Nature, 1966, 209, 807
19. P. Matzinger, P. Catalfomo, C. H. Eugster, Helv. Chim. Acta, 1972, 55, 1478
20. G. Ribes, C. Broca, P. Petit, M. Jacob, Y. Baissac, M. Manteghatti, M. Roye, Y. Sauvaire, Diabetologia, 1996, 39, A234
21. C. Broca, M. Manteghetti, R. Gross, Y. Baissac, M. Jacob, P. Petit, Y. Sauvaire, G. Ribes, Eur. J. Pharmacol. 2000, 390, 339
22. M. Seitz, O. Reiser, Curr. Opin. Chem. Biol. 2005, 9, 285
23. S. E. Franz, R. R. Watkins, L. A. Wright, B. A. Weaver, R. C. Hartage, I. Ghiviriga, G. Gumina, B. D. Feske, Synthesis, 2013, 2171
24. T. Classen, M. Korpak, M. Schölzel, J. Pietruszka, ACS Catal. 2014, 4, 1321
25. M. Korpak, J. Pietruszka, Adv. Synth. Catal. 2011, 353, 1420
26. A. Díaz-Rodríguez, W. Borzęcka, I. Lavandera, V. Gotor, ACS Catal. 2013, 4, 386
27. J. Ariza, J. Font, R. M. Ortuño, Tetrahedron, 1990, 46, 1931
28. L. J. Drummond, A. Sutherland, Tetrahedron, 2010, 66, 5349
29. M. Jacob, M. L. Roumestant, P. Viallefont, J. Martinez, Synlett, 1997, 691
30. C. Schmeck, L. S. Hegedus, J. Am. Chem. Soc. 1994, 116, 9927
31. M. Sendzik, W. Guarnieri, D. Hoppe, Synthesis, 1998, 1287
32. M. D. Swift, A. Sutherland, Org. Biomol. Chem. 2006, 4, 3889
33. W. H. Brooks, W. C. Guida, K. G. Daniel, Curr. Top. Med. Chem. 2011, 11, 760
34. B. K. Patel and A. J. Hutt, in Chirality in Drug Design and Development, ed. I. K. Reddy and R. Mehvar, New York, 2004
35. X. Cai, B. Xie, ARKIVOC, 2013, 264
36. J. M. M. Verkade, L. J. C. v. Hemert, P. J. L. M. Quaedflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29
37. A. Córdova, Acc. Chem. Res. 2004, 37, 102
38. B. List, P. Pojarliev, W. T. Biller, H. J. Martin, J. Am. Chem. Soc. 2002, 124, 827
39. A. Córdova, W. Notz, G. Zhong, J. M. Betancort, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1842
40. A. Córdova, S. Watanabe, F. Tanaka, W. Notz, C. F. Barbas III, J. Am. Chem. Soc. 2002, 124, 1866
41. A. Córdova, C. F. Barbas III, Tetrahedron Lett. 2002, 43, 7749
42. Y. Hayashi, W. Tsuboi, I. Ashimine, T. Urushima, M. Shoji, K. Sakai, Angew. Chem. Int. Ed. 2003, 42, 3677
43. I. Ibrahem, A. Córdova, Chem. Commun. 2006, 1760
44. W. Zhang, S. Saaby, K. A. Jørgensen, Angew. Chem. Int. Ed. 2004, 43, 4476
45. K. Edegger, C. C. Gruber, T. M. Poessl, S. R. Wallner, I. Lavandera, K. Faber, F. Niehaus, J. Eck, R. Oehrlein, A. Hafner, W. Kroutil, Chem. Commun. 2006, 2402
46. K. Inoue, Y. Makino, N. Itoh, Appl. Environ. Microbiol. 2005, 3633
47. W. Hummel, B. Riebel, Biotechnol. Lett. 2003, 25, 51
48. V. Höllrigl, K. Otto, A. Schmid, Adv. Synth. Catal. 2007, 349, 1337
49. F. Hollmann, A. Kleeb, K. Otto, A. Schmid, Tetrahedron: Asymmetry, 2005, 16, 3512
50. M. A. Blasco, H. Gröger, Bioorg. Med. Chem. 2014 doi: 10.1016/j.bmc.2014.06.024
51. J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, H. E. Schoemaker, M. Schürmann, F. L. van Delft, F. P. J. T. Rutjes, Adv. Synth. Catal. 2007, 349, 1332
52. J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, P. L. Alsters, F. L. van Delft, F. P. J. T. Rutjes, Tetrahedron Lett. 2006, 47, 8109