Advanced Synthesis & Catalysis
10.1002/adsc.201900178
crude lysate and 50 mg catalase were added to the
substrate solution. The pH was kept at 8.0. The reactor was
kept at 30℃ through a thermostatic water bath. The
reaction was monitored by chiral HPLC.
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5] a) S. Klutchko, C. J. Blankley, R. W. Fleming, J. M.
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961; b) S. Kotha, D. Deodhar, P. Khedkar, Org.
For the deracemization reaction, 124 mg (4 mmol) or
Biomol. Chem. 2014, 12, 9054-9091.
7
3 3
41 mg (24 mmol) NH ·BH was used. The other
components and reaction conditions were the same with
the kinetic resolution reaction.
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Preparative-scale Deracemization of rac-1a and 5a
[
7] a) L. Hu, S. Magesh, L. Chen, L. Wang, T. A. Lewis,
Y. Chen, C. Khodier, D. Inoyama, L. J. Beamer, T. J.
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The preparative-scale deracemization reaction was carried
out in a 100 mL three-necked flask equipped with a
magnetic stirrer. The rac-1a hydrochloride salt (500 mg,
2
.34 mmol) or rac-5a (400 mg, 2.26 mmol) were dissolved
in 25 or 48 ml water. The pH was carefully adjusted to a
value of pH 8.0 with ammonium hydroxide. 289 mg (9.36
3 3
mmol) or 1395 mg (45.2 mmol) NH ·BH was added,
respectively. The lyophilized E.coli cells containing
FsDAAO from 200 or 400 mL ferments was resuspended
in 25 or 20 mL water, and the crude lysate was prepared by
sonication and centrifugation. 25 or 12 mL crude lysate
and 100 mg catalase were added to the substrate solution.
The reactor was kept at 30℃ through a thermostatic water
bath. The pH was kept at 8.0. The reaction was monitored
by chiral HPLC. Upon the completion of reaction, the
proteins were removed through ultrafiltration. The solution
was freeze dried, taken up in hot ethanol and hot filtered to
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3 3
remove unreacted NH ·BH . The major parts of ethanol
were evaporated off under vacuum, and the residue was
washed with warm water. The mixture was concentrated so
that compound (S)-1a or (S)-5a was recrystallized as white
solid.
7
6, 2102-2114.
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Acknowledgements
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This work was financially supported by the National Natural
Science Foundation of China (No. 21676240).
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