ACS Catalysis
Research Article
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added. L- or D- alanine were used as amine donor employing
either (S)- or (R)-selective ωTAs, respectively. DMSO was
additionally added in selected experiments (15%, v v−1). The
mixture was shaken at 30 °C and 120 rpm. The reaction was
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Representative Example for Amination Employing
the 2-Propylamine System. Lyophilized cells of E. coli BL21
(DE3)/pET-21a-ArRmut11-ωTA (20 mg) were rehydrated in
a stock solution (800 μL) containing PLP (0.5 mM) and 2-
propylamine (1 M), adjusted to pH 11 employing 3 N HCl, for
30 min, at 30 °C and 120 rpm in a glass vial (4 mL) on an
orbital shaker. Then, DMSO (200 μL) and ketone 1 (50 mM)
were added. The vial was closed with a cap and shaken at 45 °C
and 120 rpm in an upright position. The reaction was quenched
and worked up as described above.
Determination of Optical Purity. The enantiomeric
excess of amines 2 was analyzed by GC on a chiral phase
(see Supporting Information) after derivatization to acetoa-
mides, which was performed by adding 4-(N,N-dimethylamino)
pyridine (5 mg) dissolved in acetic anhydride (100 μL). After
washing with water and drying (Na2SO4) the ee value of the
derivatized compound was measured. For more details see
Supporting Information.
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ASSOCIATED CONTENT
* Supporting Information
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2006, 3, 1191−1197.
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Information about the ω-transaminases employed, procedure
for the amination of ketones 1a−f employing (S)- and (R)-
selective ω-transaminases, chemo-enzymatic synthesis of 3-
amino-chromane from o-hydroxy-benzaldehyde, and analytics.
This material is available free of charge via the Internet at
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AUTHOR INFORMATION
Corresponding Author
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Hacksell, U. Acta Chem. Scand. 1988, B 42, 231−236.
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(22) Johansson, A. M.; Nilsson, J. L. G.; Karlen, A.; Hacksell, U.;
Author Contributions
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L. J. Med. Chem. 1987, 30, 1827−1837.
The manuscript was written through contributions of all
authors. All authors have given approval to the final version of
the manuscript.
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2010, 66, 9790−9797.
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Notes
The authors declare no competing financial interest.
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Tetrahedron Lett. 1994, 35, 3091−3094.
ACKNOWLEDGMENTS
■
The research leading to these results has received funding from
the European Union’s Seventh Framework Programme FP7/
2007-2013 under grant agreement no. 245144 (AmBioCas).
D.P. and C.F. acknowledge the Federal Ministry of Economy,
Family and Youth (BMWFJ), the Federal Ministry of Traffic,
Innovation and Technology (bmvit), the Styrian Business
Promotion Agency SFG, the Standortagentur Tirol and ZIT-
Technology Agency of the City of Vienna through the
COMET-Funding Program managed by the Austrian Research
Promotion Agency FFG.
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dx.doi.org/10.1021/cs400002d | ACS Catal. 2013, 3, 555−559