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Preparative scale
M. D.; Turner, N. J.; Rozzell, J. D. Chem. Commun. (Camb.)
2
009, (16), 2127. doi:10.1039/b902995h; (f) Savile, C. K.;
The amine (1 mmol) dissolved in DMSO (0.5 mL) was either
added to a solution of CHAO (final concentration 1.2 U/mL)
and borane–ammonia complex (617 mg, 20.0 mmol; for
the deracemization of 9, 926 mg, 30 mmol) in 100 mmol/L
phosphate buffer (pH 7, 20 mL) or to a suspension of
whole cells overexpressing CHAO (OD600 5) resuspended
in 100 mmol/L phosphate buffer (pH 7, 20 mL) and borane–
ammonia complex (617 mg, 20.0 mmol). The mixture was
shaken at 200 rpm at 30 °C on an orbital shaker for 18 h,
before the pH of the reaction mixture was carefully adjusted
to 2 with 2 mol/L HCl. The suspension was centrifuged
Janey, J. M.; Mundorff, E. C.; Moore, J. C.; Tam, S.; Jarvis, W.
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010.03.003.
(
(
(
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6
8 (5), 987. doi:10.1073/pnas.68.5.987.
(
6300g, 20 min) and the supernatant was basified to pH 9
7) (a) Huh, J. W.; Yokoigawa, K.; Esaki, N.; Soda, K. J. Ferment.
with 5 mol/L NaOH. The aqueous layer was extracted 3
times with DCM, the organic layers were combined, and
an aliquot (1 mL) was analyzed for the content of amine
and the corresponding ketone and alcohol. The organic sol-
vent was concentrated (25 mL) and extracted 3 times with
Bioeng. 1992, 74 (3), 189. doi:10.1016/0922-338X(92)90082-
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; (b) Huh, J. W.; Yokoigawa, K.; Esaki, N.; Soda, K. Biosci.
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5
(
1
mol/L HCl. The aqueous layers were combined, basified
(
to pH 9 with 5 mol/L NaOH, and extracted 3 times with
DCM. The organic layers were combined, washed with
brine, dried over anhydrous sodium sulphate, and filtered.
Evaporation of the solvent gave 83 mg (69% yield) of (R)-
Pantaleone, D. P.; Taylor, P. P.; Fotheringham, I. G.; Ager,
D. J.; Turner, N. J. Tetrahedron Lett. 2002, 43 (4), 707. doi:10.
1016/S0040-4039(01)02233-X.
(9) (a) For cloning and characterization of monoamine oxidase
from A. niger see Schilling, B.; Lerch, K. Biochim. Biophys.
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Gen. Genet. 1995, 247 (4), 430. doi:10.1007/BF00293144.
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M.; Turner, N. J. Angew. Chem. Int. Ed. 2002, 41 (17), 3177.
doi:10.1002/1521-3773(20020902)41:17<3177::AID-
ANIE3177>3.0.CO;2-P; (b) Carr, R.; Alexeeva, M.; Enright,
A.; Eve, T. S. C.; Dawson, M. J.; Turner, N. J. Angew. Chem.
Int. Ed. 2003, 42 (39), 4807. doi:10.1002/anie.200352100.
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Humphrey, C. E.; Turner, N. J. ChemBioChem 2005, 6 (4),
9
using crude enzyme extracts, 75 mg (62% yield) of (R)-9
using whole cells, 101 mg (75% yield) of (R)-14 using crude
enzyme extracts, and 92 mg (69% yield) of (R)-14 using
crude enzyme extracts. The enantiomeric ratio of the ob-
tained products was determined after derivatization of an ali-
quot of the product as described before.
(
Acknowledgements
We thank A. Corriveau, S. Deschamps, and C. Beaulieu
for their expert help in various analytical analyses, and K.
Morley for suggestions and comments on the manuscript.
(
(
6
37. doi:10.1002/cbic.200400329.
12) (a) Dunsmore, C. J.; Carr, R.; Fleming, T.; Turner, N. J. J. Am.
Chem. Soc. 2006, 128 (7), 2224. doi:10.1021/ja058536d; (b)
Bailey, K. R.; Ellis, A. J.; Reiss, R.; Snape, T. J.; Turner, N. J.
Chem. Commun. (Camb.) 2007, (35), 3640. doi:10.1039/
b710456a.
13) Köhler, V.; Bailey, K. R.; Znabet, A.; Raftery, J.; Helliwell,
M.; Turner, N. J. Angew. Chem. Int. Ed. 2010, 49 (12), 2182.
doi:10.1002/anie.200906655.
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