Abstract
Reduction of acetophenone by Daucus carota hairy root cultures afforded (S)-phenylethanol in high yield (96%) and excellent enantiomeric excess (ee ≥ 98%). Aromatic ketones, keto esters, and a simple aliphatic ketone were reduced with good stereoselectivity (ee = 62–98%) and moderate to high chemical yields (25–90%).
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Y Akakabe M Takahashi M Kamezawa K Kikuchi H Tachibana T Ohtani Y Naoshima (1995) ArticleTitleBiocatalytic preparation of chiral alcohols by enantioselective reduction with immobilized cells of carrot J. Chem. Soc., Perkin Trans. 1 1295–1298
F Baldassare G Bertoni C Chiappe F Marioni (2000) ArticleTitlePreparative synthesis of chiral alcohols by enantioselective reduction with Daucus carota root as biocatalyst J. Mol. Catal. B: Enzyme 11 55–58 Occurrence Handle10.1016/S1381-1177(00)00189-2
B Baskar S Ganesh TS Lokeswari A Chadka (2004) ArticleTitleHighly stereoselective reduction of 4-aryl-2-oxobut-3-enoic carboxylic esters by plant cell culture of Daucus carota J. Mol. Catal. B: Enzyme 27 13–17 Occurrence Handle10.1016/j.molcatb.2003.09.004
G Bécard Y Piché (1992) Establishment of vesicular–arbuscular mycorrhiza in root organ culture: review and proposed methodology J Norris D Read A Varma (Eds) Techniques for the Study of Mycorrhiza. Academic Press New York 89–108
BT Cho (2002) ArticleTitleBoron-based reducing agents for the asymmetric reduction of functionalized ketones and ketimines Aldrichim. Acta 35 3–16
EJ Corey CJ Helal (1998) ArticleTitleReduction of carbonyl compounds with chiral oxazaborolidine catalysts: a new paradigm for enantioselective catalysis and a powerful new synthetic method Angew. Chem. Intern. Edit. 37 1986–2012 Occurrence Handle10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z
K Ishihara H Hamada T Hirata N Nakajima (2003) ArticleTitleBiotransformation using plant cultured cells J. Mol. Catal. B: Enzyme 23 145–170 Occurrence Handle10.1016/S1381-1177(03)00080-8
W Kroutil H Mang K Edegger K Faber (2004) ArticleTitleRecent advances in the biocatalytic reduction of ketones and oxidation of sec-alcohols Curr. Opin. Chem. Biol. 8 120–126 Occurrence Handle10.1016/j.cbpa.2004.02.005 Occurrence Handle15062771
WK Maczka A Mironowicz (2004) ArticleTitleEnantioselective reduction of bromo- and methoxy-acetophenone derivatives using carrot and celeriac enzymatic system Tetrahedron: Asymmetry 15 1965–1967 Occurrence Handle10.1016/j.tetasy.2004.05.033
K Nakamura R Yamanaka T Matsuda T Harada (2003) ArticleTitleRecent developments in asymmetric reduction of ketones␣with biocatalysts Tetrahedron: Asymmetry 14 2659–2681 Occurrence Handle10.1016/S0957-4166(03)00526-3
R Noyori S Hashiguchi (1997) ArticleTitleAsymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes Accounts Chem. Res. 30 97–102 Occurrence Handle10.1021/ar9502341
D Tepfer (1989) Ri T-DNA from Agrobacterium rhizogenes: a source of genes having applications in rhizosphere biology and plant development, ecology and evolution T Kosuge EW Nester (Eds) Plant–Microbe Interactions NumberInSeriesVol. 3. McGraw-Hill Publishing New York 294–342
JS Yadav S Nanda P Thirupathi Reddy A Bhaskar Rao (2002) ArticleTitleEfficient enantioselective reduction of ketones with Daucus carota root J. Org. Chem. 67 3900–3903 Occurrence Handle10.1021/jo010399p Occurrence Handle12027710
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Caron, D., Coughlan, A.P., Simard, M. et al. Stereoselective reduction of ketones by Daucus carota hairy root cultures. Biotechnol Lett 27, 713–716 (2005). https://doi.org/10.1007/s10529-005-5187-y
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DOI: https://doi.org/10.1007/s10529-005-5187-y