Regio- and stereoselective concurrent oxidations with whole cell biocatalyst: Simple and green syntheses of enantiopure 1,2-diols via oxidative kinetic resolution

ACS Catalysis

Volumn 1, Issue 6, 2011, Pages 591-596

  Jia, Xin ^a   Xu, Yi ^a   Li, Zhi ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

2 diols; concurrent oxidations; enantiopure 1; enantioselective synthesis; enzyme catalysis; Sphingomonas sp. HXN 200; tandem biocatalysis

Indexed keywords

2-DIOLS; BIOCATALYSIS; CONCURRENT OXIDATIONS; ENANTIOPURE 1; ENANTIOSELECTIVE SYNTHESIS; ENZYME CATALYSIS; SPHINGOMONAS SP;

ALDEHYDES; BIOCATALYSTS; CARBOXYLIC ACIDS; ETHYLENE GLYCOL; STEREOSELECTIVITY;

OXIDATION;

EID: 79958239883     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs200099k     Document Type: Article

References (38)

1. Bronson, J.; Ghazzouli, I.; Hitchcock, M.; Webb, R.; Martin, J. J. Med. Chem. 1989, 32, 1457-1463
2. Ho, H.; Woods, K.; Bronson, J.; Boeck, H.; Martin, J.; Hitchcock, M. Mol. Pharmacol. 1992, 41, 197-202
3. Piergentili, A.; Quaglia, W.; Giannella, M.; Bello, F.; Bruni, B.; Buccioni, M.; Carrieri, A.; Ciattini, S. Bioorg. Med. Chem. 2007, 15, 886-896
4. Durgam, G.; Tsukahara, R.; Makarova, N.; Walker, M.; Fujiwara, Y.; Pigg, K.; Baker, D.; Sardar, V.; Parrill, A.; Tigyi, G.; Miller, D. Bioorg. Med. Chem. Lett. 2006, 16, 633-640
5. Di Fabio, R.; Pietra, C.; Thomas, R.; Ziviani, L. Bioorg. Med. Chem. Lett. 1995, 5, 551-554
6. Yong-moon, C.; Choon-gil, K.; Young-sun, K.; Han-ju, Y.; Hyun-seok, L.; Bon-chul, K.; Eun-ho, L.; Dae-joong, I.; Yu-jin, S. U.S. Patent 0674530, 2006.
7. Kurosaki, Y.; Fukuda, T.; Iwao, M. Tetrahedron 2005, 61, 3289-3303
8. Yamazaki, N.; Atobe, M.; Kibayashi, C. Tetrahedron Lett. 2001, 42, 5029-5032
9. Ewing, D.; Glacon, V.; Len, C.; Mackenzie, G. New J. Chem. 2005, 29, 1461-1468
10. Atobe, M.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 2004, 69, 5595-5607
11. Kolb, H.; VanNieuwenhze, H.; Sharpless, B. Chem. Rev. 1994, 94, 2483-2547
12. Zaitsev, A.; Adolfsson, H. Synthesis 2006, 11, 1725-1756
13. Doo, S.; Sang, S.; Eun, K.; Han, Y.; Soon, H.; Yil, S.; Choong, E. Adv. Synth. Catal. 2006, 348, 2560-2564
14. Ohkuma, T.; Utsumi, N.; Watanabe, M.; Tsutsumi, K.; Arai, N.; Murata, K. Org. Lett. 2007, 9, 2565-2567
15. Tokunaga, M.; Larrow, J.; Kakiuchi, F.; Jacobsen, E. Science 1997, 277, 936-938
16. Schaus, S.; Brandes, B.; Larrow, J.; Tokunaga, M.; Hansen, K.; Gould, A.; Furrow, M.; Jacobsen, E. J. Am. Chem. Soc. 2002, 124, 1307-1315
17. Boyd, D. R.; Sharma, N. D.; Bowers, N. I.; Brannigan, I. N.; Groocock, M. R.; Malone, J. F.; McConville, G.; Allen, Ch. C. R. Adv. Synth. Catal. 2005, 347, 1081-1089
18. Lee, K.; Gibson, D. T. J. Bacteriol. 1996, 178, 3353-3356
19. Balint, J.; Egri, G.; Kolbert, A.; Dianoczky, C.; Fogassy, E.; Novak, L.; Poppe, L. Tetrahedron: Asymmetry 1997, 10, 4017-4028
20. Pallavicini, M.; Villa, L.; Cesarotti, E.; Antognazza, P. J. Chem. Res. 1994, 6, 232-233
21. Kamal, A.; Sandbhor, M.; Ahmed, K. Tetrahedron: Asymmetry 2003, 14, 3861-3866
22. Chen, C.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. Am. Chem. Soc. 1982, 104, 7294-7299
23. Weijers, C. Tetrahedron: Asymmetry 1997, 8, 639-647
24. Hao, J.; Zu-yi, L.; Xiao-wei, D. Org. Biomol. Chem. 2004, 2, 408-414
25. Monterde, M.; Lombard, M.; Archelas, A.; Cronin, A.; Arand, M.; Furstoss, R. Tetrahedron: Asymmetry 2004, 15, 2801-2805
26. Manoj, K.; Archelas, A.; Baratti, J.; Furstoss, R. Tetrahedron 2001, 57, 695-701
27. Xu, W.; Xu, J.; Pan, J.; Gu, Q.; Wu, X. Org. Lett. 2006, 8, 1737-1740
28. Suzuki, T.; Kasai, N.; Minamiura, N. Tetrahedron: Asymmetry 1994, 5, 239-246
29. Moreno-Dorado, F. J.; Guerra, F. M.; Ortega, M. J.; Zubía, E.; Massanet, G. M. Tetrahedron: Asymmetry 2003, 14, 503-510
30. Liu, Z.; Michel, J.; Wang, Z.; Witholt, B.; Li, Z. Tetrahedron: Asymmetry 2006, 17, 47-52
31. Li, Z.; Feiten, H.; Beilen, J.; Duetz, W.; Witholt, B. Tetrahedron: Asymmetry 1999, 10, 1323-1333
32. Li, Z.; Feiten, H.; Chang, D.; Duetz, W.; van Beilen, J.; Witholt, B. J. Org. Chem. 2001, 66, 8424
33. Jia, X.; Wang, Z.; Li, Z. Tetrahedron: Asymmetry 2008, 19, 407-415
34. Effenberger, F.; Null, V.; Ziegler, T. Tetrahedron Lett. 1992, 33, 5157-5160
35. Gerhardt, W. W.; Noga, D. E.; Hardcastle, K. I.; García, A. J.; Collard, D. M.; Weck., M. Biomacromolecules 2006, 7, 1735-1742
36. Xu, Y.; Jia, X.; Pank, S.; Li, Z. Chem. Commun. 2009, 1481-1483
37. Matos, J.; Smith, M.; Wong, C. Bioorg. Chem. 1985, 13, 121-130
38. Wong, C.; Matos, J. J. Org. Chem. 1985, 50, 1992-1994