Asymmetric hydrogenation of the C-C double bond of enones with the reductases from Nicotiana tabacum

Chemistry Letters

Volumn , Issue 8, 2000, Pages 850-851

  Hirata, Toshifumi ^a   Shimoda, Kei ^a   Gondai, Takayuki ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034337490     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.850     Document Type: Article

References (18)

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7. 4 (40 to 60% satn.). The crude enzyme soin obtained was desalted and then applied to a DEAE-Toyopearl column with a 0-0.5 M linear gradient of NaCl in 50 mM Tris-HCl buffer (pH 8.0) containing 1.0 mM 2-mercaptoethanol and 1.0 mM dithiothreitol (buffer A) to give three enone reductase fractions, which contained the 44, 74 and 90 kDa proteins, respectively. Each of the fractions was further purified on a hydroxylapatite column with buffer A and a Red-Toyopearl column with buffer A containing a 0-1.0 M linear gradient of NaCl.
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9. The mixture (2 mL) of enone (100 μmol), NADPH (200 μmol), Triton X-100 (0.1%), and enzyme preparation (5 μg) in 50 mM Tris-HCl buffer (pH 8.0) containing 1.0 mM 2-mercaptoethanol and 1.0 mM dithiothreitol was incubated at 35 °C for 8 h. After incubation, the reaction mixture was subjected to GLC and GC-MS analyses, and then the products were purified by column chromatography on silica gel. The absolute configurations and enantiomeric purities of the products were determined by circular dichroism (CD) spectra and the peak area of the corresponding enantiomers in the GLC analyses on CP cyclodextrin β 236M-19 column.
10. 2-Me), 6.69 (1H, t, J = 4.3 Hz, >C=CH-).
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14. 288 +2480}.
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17. 288 +2351 (c 0.12, MeOH).
18. 288 -2483 (c 0.1, MeOH).