Asymmetric Bioreduction of C=C Bonds using Enoate Reductases
FULL PAPERS
808C, hold 2 min, 308CminÀ1 to 1808C, hold 2 min. Reten-
tion times: (R)-3b and (S)-3b 10.35 and 10.62 min, respec-
tively. Temperature programme for 4b: 808C hold 2 min,
58CminÀ1 to 1058C, 108CminÀ1, hold 4 min. Retention
times: (R)-4b and (S)-4b 6.34 and 6.47 min, respectively.
Temperature programme for 5b: 708C hold 10 min,
308CminÀ1 to 1808C, hold 4 min. Retention times: (S)-5b
and (R)-5b 11.19 and 11.27 min, respectively. Temperature
programme for 8b: 1308C hold 2 min, 108CminÀ1 to 1608C
hold 6 min. Retention times: (S)-8b and (R)-8b 8.74 and
8.89 min, respectively.
The enantiomeric excess of 6b and 10b was determined
using a b-cyclodextrin capillary column (CP-Chirasil-DEX
CB, 25 m, 0.32 mm, 0.25 mm film). Temperature programme
for 6b: 908C hold 2 min, 48CminÀ1 to 1158C, 208CminÀ1 to
1808C, hold 2 min. Retention times: (R)-6b and (S)-6b 6.42
and 6.74 min, respectively. Temperature programme for 10b:
1058C hold 5 min, 18CminÀ1 to 1158C, hold 1 min,
208CminÀ1 to 1808C, hold 2 min. Retention times: (S)-10b
and (R)-10b 7.90 and 8.08 min, respectively.
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Enantioenriched 3b or 4b obtained by reduction of 3a or 4a
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ter in a 1 mm plexiglas cuvette. The scan was performed be-
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ly synthesised reference material. Enantioenriched 8b
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was performed between 300 and 230 nm. 8b showed CD
[q]251 =À5.3 and 9b showed CD [q]272 =À14, which are in
agreement with literature data: (R)-8b CD [q]253 =À840,
(R)-9b [q]272 =À76.9;[36,37] the corresponding racemates gave
a flat baseline.
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Acknowledgements
We would like to thank Nicole Müller, Tea Pavkov and Klaus
Zangger for their excellent technical assistance.
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