Asymmetric reduction of substituted α- and β-ketoesters by Bacillus pumilus Phe-C3

Tetrahedron Asymmetry

Volumn 19, Issue 11, 2008, Pages 1347-1351

  He, Chunmao ^a,b   Chang, Dongliang ^a,c   Zhang, Jie ^c  

^a GUANGZHOU INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA KETOESTER; BETA OXOCARBOXYLIC ACID ESTER; ESTER DERIVATIVE; PHENYL GROUP;

ARTICLE; BACILLUS PUMILUS; BIOCATALYST; BIOTRANSFORMATION; CATALYST; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ENZYME SUBSTRATE; NONHUMAN; PRIORITY JOURNAL; REDUCTION; STEREOCHEMISTRY;

EID: 47049089266     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.05.003     Document Type: Article

References (63)

1. Daubmann T., Hennemann H.G., and Rosen T.C. Chem. Ing. Tech. 78 (2006) 249-255
2. Hasegawa J., and Nagashima N. In: Patel R.N. (Ed). Production of Chiral β-Hydroxy Acids and its Application in Organic Syntheses. Stereoselective Biocatalysis (2000), Marcel Dekker, New York 343-363
3. Karanewsky D.S., Badia M.C., Ciosek Jr. C.P., Robel F., Sofia M.J., Simpkins L.M., DeLange B., Harrity T.W., Biller S.A., and Gorden E.M. J. Med. Chem. 33 (1990) 2925-2956
4. Kula M.R., and Kragl U. In: Patel R.N. (Ed). Dehydrogenases in the Synthesis of Chiral Compounds. Stereoselective Biocatalysis (2000), Marcel Dekker, New York 839-866
5. Zhou B., Gopalan A.S., Vanmiddlesworth F., Shieh W.R., and Sih C.J. J. Am. Chem. Soc. 105 (1983) 5925-5926
6. Wang G.J., and Hollingsworth R.I. Tetrahedron: Asymmetry 20 (1999) 1895-1901
7. Genet J.P., Pinel C., Ratovelomanana-Vidal V., Mallart S., and Pfister X. Tetrahedron: Asymmetry 5 (1994) 675-690
8. Trost B.M., and Hanson P.R. Tetrahedron Lett. 35 (1994) 8119-8122
9. Kitamura M., Ohkuma T., Takaya H., and Noyori R. Tetrahedron Lett. 29 (1988) 1555-1556
10. Benincori T., Cesarotti E., Piccolo O., and Sannicolo F. J. Org. Chem. 65 (2000) 2043-2047
11. LeBlond C., Wang J., Liu J., Andrews A.T., and Sun Y.K. J. Am. Chem. Soc. 121 (1999) 4920-4921
12. Andres C., Delgado M., Pedrosa R., and Rodrigurz R. Tetrahedron Lett. 34 (1993) 8325-8328
13. Belzecki C., and Panfil I. J. Org. Chem. 44 (1979) 1212-1218
14. Iwasaki G., Kimura R., Numao N., and Knodo K. Chem. Pharm. Bull. 37 (1989) 280
15. Tang L., and Deng L. J. Am. Chem. Soc. 124 (2002) 2871-2872
16. Herold P., Indolses A.F., Studer M., Jalett H.P., Siegrist U., and Blaser H.U. Tetrahedron 56 (2000) 6497-6499
17. Faber K. Biotransformations in Organic Chemistry (1995), Springer, Berlin pp 160-168
18. Zhou B., Gopalan A.S., Vanmiddlesworth F., Shieh W.R., and Sih C.J. J. Am. Chem. Soc. 105 (1983) 5925-5926
19. Santaniello E., Casati R., and Milani F. J. Chem. Res. (S) (1984) 132-133
20. Tricone A., Nicolaus B., Lama L., Marsiglia F., and Gambacorta A. Biotechnol. Lett. 13 (1991) 31-34
21. Fuganti C., Grasselli P., Casati P., and Carmeno M. Tetrahedron Lett. 26 (1985) 101-104
22. Ribeiro J.B., Ramos M.d.C.K.V., Neto F.R.d.A., Leite S.G.F., and Antunes O.A.C. J. Mol. Catal. B: Enzymol. 24-25 (2003) 121
23. Vitinius U., Schaffner K., and Demuth M. J. Photochem. Photobiol. A: Chem. 169 (2005) 197
24. Dao D.H., Kawai Y., Hida K., Hornes S., Nakamura K., Ohno A., Okamura M., and Akasaka T. Bull. Chem. Soc. Jpn. 71 (1998) 425-432
25. Chalda A., Manohar M., Soundarajan T., and Loksewari T.S. Tetrahedron: Asymmetry 7 (1996) 1571-1572
26. Oda S., Inada Y., Kobayshi A., and Ohta H. Biosci., Biotechnol., Biochem. 62 (1998) 1762-1767
27. Fadnavis N.W., and Radhika K.R. Tetrahedron: Asymmetry 15 (2004) 3443-3447
28. Kaluzna I., Andrew A.A., Bonilla M., Martzen M.R., and Stewart J.D. J. Mol. Catal. B: Enzym. 17 (2002) 101-105
29. Padhi S.K., Pandian N.G., and Chadha A. J. Mol. Catal. B: Enzymol. 29 (2004) 25
30. Ma D.Y., Zheng Q.Y., Wang D.X., and Wang M.X. Org. Lett. 8 (2006) 3231-3234
31. Azerad R., and Buisson D. In: Servi S. (Ed). Microbial Reagents in Organic Synthesis (1992), Kluwer Academic, Dordrecht, The Netherlands 421-440
32. Nakamura K., Fuji M., and Ida Y. Tetrahedron: Asymmetry 12 (2001) 3147-3153
33. Padhi S.K., and Chadha A. Tetrahedron: Asymmetry 16 (2005) 2790-2798
34. Huerta F.F., Santosh Laxmi Y.R., and Backvall J.-E. Org. Lett. 2 (2000) 1037-1040
35. Chadha A., and Manohar M. Tetrahedron: Asymmetry 6 (1995) 651-652
36. Baldaro E., Darrigo P., Pedrocchi-Fantoni G., Rosell C.M., Servi S., Tagliani A., and Terreni M. Tetrahedron: Asymmetry 4 (1993) 1031-1034
37. Hsu S.H., Wu S.S., Wang Y.F., and Wong C.H. Tetrahedron Lett. 31 (1990) 6403-6406
38. Huang S.H., and Tsai S.W. J. Mol. Catal. B: Enzym. 28 (2004) 65-69
39. Sharma A., and Chattopadhyay S. J. Mol. Catal. B: Enzym. 10 (2000) 531-534
40. Xu C., and Yaun C. Tetrahedron 61 (2005) 2169-2186
41. Wilson W.K., Baca S.B., Barber Y.J., Scallen T.J., and Morrow C.J. J. Org. Chem. 48 (1983) 3960
42. Boaz N.W. J. Org. Chem. 57 (1992) 4289
43. Itoh T., Fakagi Y., and Nishigama S. J. Org. Chem. 56 (1991) 1521
44. Feichter C., Faber K., and Griengl H. Tetrahedron Lett. 30 (1989) 551
45. Zhang J., Duetz W.A., Witholt B., and Li Z. Chem. Commun. (2004) 2120-2121
46. Sheldon R.A. Chim. Oggi. (1991) 35
47. Davignon J. Atherosclerosis ID Res. Alert 2 (1997) 243-252
48. Li O.S., Ogawa J., Schmid R.D., and Shimizu S. FEBS Lett. 508 (2001) 249
49. Foster B.J., and Lavagnino E.R. Drugs of the Future Vol. 11 (1986), Prous Science, Barcelona, Spain 134-200
50. Salvi N.A., and Chattopadhahy S. Bioorg. Med. Chem. 14 (2006) 4918-4922
51. Furlemmeier, A.; Quitt, P.; Vogler, K.; Lanz, P. U.S. Patent, 3,957,758, 1976.
52. Mill, J.; Schmiegel, K. K.; Shaw, W. N. U.S. Patent, 4,391,826, 1983.
53. Saravanan P., and Singh V.K. Tetrahedron Lett. 39 (1998) 167-170
54. Chen Y.Z., Xu J.G., Xu X.Y., Xia Y., Lin H., Xia S.W., and Wang L.X. Tetrahedron: Asymmetry 18 (2007) 2537-2540
55. Svendsen A., and Boll P.M. Tetrahedron 29 (1973) 4251-4258
56. Ryuhel, W.; Nobuya, I. EP 1201647 A2, 2001.
57. Carnell A.J., Head R., Basset D., and Schneider M. Tetrahedron: Asymmetry 15 (2004) 821-825
58. Kitamura M., Ohkuma T., Takaya H., and Noyori R. Tetrahedron Lett. 29 (1988) 1555-1556
59. Yasohara Y., Kizaki N., Hasegawa J., Wada M., Kataoka M., and Shimizu S. Tetrahedron: Asymmetry 12 (2001) 1713-1718
60. Deol B.S., Ridly D.D., and Simpson G.W. Aust. J. Chem. 29 (1976) 2459-2467
61. Brower P.L., Butler D.E., Deering C.F., Le T.V., Millar A., Nanninga T.N., and Roth B.D. Tetrahedron Lett. 33 (1992) 2279-2282
62. Feenstra R.W., Stokkingreef E.H.M., Nivard R.J.F., and Ottenheijin H.C.J. Tetrahedron 44 (1988) 5583-5595
63. Dale J.A., Duff D.L., and Mosher H.S. J. Org. Chem. 33 (1968) 3245