Enantiocontrol in the bakers' yeast reduction of trifluoroacetylbiphenyl derivatives

Tetrahedron Letters

Volumn 40, Issue 10, 1999, Pages 1953-1956

  Fujisawa, T ^a   Tanaka, S ^a   Onogawa, Y ^a   Shimizu, M ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

Asymmetric reduction; Bakers' yeast; Methanethiosulfonate; Trifluoroacetylbiphenyls

Indexed keywords

BIPHENYL DERIVATIVE; THIOMESYLIC ACID METHYL ESTER; TRIFLUOROACETIC ACID;

ARTICLE; DISULFIDE BOND; ENANTIOMER; NONHUMAN; REDUCTION; SACCHAROMYCES CEREVISIAE;

SACCHAROMYCES CEREVISIAE;

EID: 0033525807     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00052-0     Document Type: Article

References (60)

1. L. Poppe L. Novák Selective Biocatalysis 1992 VCH Weinheim
2. GM. Whitesides C-H. Wong Angew. Chem. Int. Ed. Engl. 24 1985 617 718
3. A.M. Kilbanov Acc. Chem. Res. 23 1990 114 120
4. S. Servi H.-J. Rehm G. Reed Biotechnology 8a 1998 VCH Weinheim 364 389
5. C.J. Sih C.-H. Chen Angew. Chem. Int. Ed. Engl. 23 1984 570 578
6. S. Servi Synthesis 5 1990 1 25
7. R. Csuk B.I. Glänzer Chem. Rev. 91 1991 49 97
8. B. Wipf E. Kupfer R. Berrtazzi H.G.W. Leuenberger Helv. Chim. Acta 66 1983 485 488
9. M. Bucciorelli A. Forni I. Moretti G. Torre Synthesis 1983 897 899
10. B. Sonnleitner F. Giovannini A. Fiechter J. Biotech. 3 1985 33 45
11. K. Ushio K. Inoue K. Nakamura S. Oka A. Ohno Tetrahedron Lett. 27 1986 2657 2660
12. D. Seebach S. Roggo T. Maetzke H. Braunschweiger J. Cercus M. Krieger Helv. Chim. Acta 70 1987 1605 1615
13. T. Sugai H. Ohta Agric. Biol. Chem. 53 1989 2009 2010
14. K. Nakamura M. Higaki K. Ushio S. Oka A. Ohno Tetrahedron Lett. 26 1985 4213 4216
15. K. Nakamura K. Inoue K. Ushio S. Oka A. Ohno J. Org. Chem. 53 1988 2589 2593
16. Y. Naoshima H. Hasegawa Chem. Lett. 1987 2379 2382
17. T. Sakai T. Nakamura K. Fukuda E. Amano M. Utaka A. Takeda Bull. Chem. Soc. Jpn. 59 1986 3185 3188
18. K. Nakamura K. Inoue K. Ushio S. Oka A. Ohno J. Org. Chem. 53 1988 2589 2593
19. K. Nakamura K. Kawai S. Oka A. Ohno Tetrahedron Lett. 30 1989 2245 2246
20. K. Nakamura T. Miyai K. Inoue S. Kawasaki S. Oka A. Ohno Biocatalysis 3 1990 17 24
21. K. Nakamura K. Inoue K. Ushio S. Oka A. Ohno Chem. Lett. 1987 679 682
22. K. Nakamura A. Kawai S. Oka A. Ohno Bull. Chem. Soc. Jpn. 62 1989 875 879
23. K. Nakamura Y. Kawai A. Ohno Tetrahedron Lett. 31 1990 267 270
24. K. Ushio K. Ebara T. Yamashita Enzyme Microb. Technol. 13 1991 834 839
25. R.P. Lanzilotta D.G. Bradley C.C. Beard Appl. Microbiol. 29 1975 427 429
26. G. Fráter Helv. Chim. Acta 62 1979 2829 2832
27. B.-n. Zhou A.S. Gopalan F. VanMiddlesworth W.-R. Shieh C.J. Sih J. Am. Chem. Soc. 105 1983 5925 5926
28. K. Nakamura K. Ushio S. Oka A. Ohno S. Yasui Tetrahedron Lett. 25 1984 3979 3983
29. K. Mori H. Mori T. Sugai Tetrahedron 41 1985 919 925
30. C. Fuganti P. Grasselli Tetrahedron Lett. 26 1985 101 104
31. W.-R. Shieh A.S. Gopalan C.S. Sih J. Am. Chem. Soc. 107 1985 2993 2994
32. D.W. Brooks R.P. Kellog C.S. Cooper J. Org. Chem. 52 1987 192 196
33. A. Manzocchi R. Casati A. Fiecchi E. Santaniello J. Chem. Soc. Perkin Trans. 1 1987 2753 2757
34. PIR protein sequence database http://www.genome.ad.jp/dbget-bin/www_bfind?pir Release 57.0, Jun 98, National Biomedical Research Foundation
35. E.P. Whitehead B.R. Rabin Biochem. J. 90 1964 532 539
36. K. Wallenfels A. Arens Biochem. Z. 332 1959 217 246
37. J.E. Hayes S.F. Velick J. Biol. Chem. 207 1954 225 244
38. G. Biesecker J.I. Harris J.C. Thierry J.E. Walker A.J. Wonactt Nature 266 1977 328 333
39. C.D. Clark-Walker H.C. Robinson J. Chem. Soc. 1961 2810 2812
40. K. Geiss B. Seuring B. Seuring R. Pieter D. Seebach Angew. Chem. Int. Ed. Engl. 13 1974 479 480
41. E. Emori T. Arai H. Sasai M. Shibasaki J. Am. Chem. Soc. 120 1998 4043 4044 and references cited therein
42. M. Oki W. Funakoshi A. Nakamura Bull. Chem. Soc. Jpn. 44 1971 828 832
43. T. Fujisawa K. Hata T. Kojima Chem. Lett. 1973 287 290
44. A. Fava A. Ilicete E. Camera J. Am. Chem. Soc. 79 1957 833 838
45. J.F. Roesler J. Leslie G. Goriu J. Org. Chem. 29 1964 1488 1490
46. R. Freter E. Pohl J.M. Wilson D.J. Hupe J. Org. Chem. 44 1979 1771 1774
47. B. Nelander S. Sunner J. Am. Chem. Soc. 94 1972 3576 3577
48. Y.H. Khim L. Field J. Org. Chem. 37 1972 2714 2720
49. T. Sato T. Fujisawa Biocatalysis 3 1990 1 15 and the references cited therein
50. R. Hayakawa K. Nozawa M. Shimizu T. Fujisawa Tetrahedron Lett. 39 1998 67 70
51. G.L. Ellman Arch. Biochem. Biophys. 82 1959 70 77
52. Y. Shechter M. Rubinstein R. Becker Z. Bohak Eur. J. Biochem. 58 1975 123 131
53. P. Berglund G. DeSantis M.R. Stabile X. Shang M. Gold R.R. Bott T.P. Graycar T.H. Lau C. Mitchinson J.B. Jones J. Am. Chem. Soc. 119 1997 5265 5266
54. For reviews: G.L. Kenyon T.W. Bruice Methods Enzymol. 47 1977 407 430
55. R. Wynn F.M. Richards Methods Enzymol. 251 1995 351 356
56. D.M. Walba H.A. Razavi N.A. Clark D.S. Parnar J. Am. Chem. Soc. 110 1988 8686 8691
57. H. Nohira J. Synth. Org. Chem. Jpn. 49 1991 467 474
58. T. Tanaka H.F. Deluca Y. Kobayashi N. Ikekawa Arch. Biochem. Biophys. 229 1984 348 354
59. T. Fujisawa Y. Onogawa A. Sato T. Mitsuya M. Shimizu Tetrahedron 54 1998 4267 4276
60. D.J. Smith E.T. Maggio G.L. Kenyon Biochemistry 14 1975 766 771