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The enzymatic formation of acetolactate from the 2-ketoacid pyruvate has already been demonstrated (see Ref. [13]) but no ketones were used as substrates.
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The absolute configuration of (5)-acetolactate was determined by CD spectroscopy; see: The absolute configuration of (R)-PAC was determined by chiral-phase HPLC analysis with the (R)-PAC formed by ScPDC. The absolute configurations of (TJ)-Ia and (R)-2a were determined by optical rotation; see Refs. [16] and [17].
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The absolute configuration of (5)-acetolactate was determined by CD spectroscopy; see: A. Baykal, S. Chakraborty, A. Dodoo, F. Jordan, Bioorg. Chem. 2006, 34, 380. The absolute configuration of (R)-PAC was determined by chiral-phase HPLC analysis with the (R)-PAC formed by ScPDC. The absolute configurations of (TJ)-Ia and (R)-2a were determined by optical rotation; see Refs. [16] and [17].
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The absolute configuration of (S)-acetoin was also determined by CD specroscopy; see
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The absolute configuration of (S)-acetoin was also determined by CD specroscopy; see: A. Baykal, S. Chakraborty, A. Dodoo, F. Jordan, Bioorg. Chem. 2006, 34, 380.
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23
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85036770029
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We have tested the recombinant enzymes benzaldehyde lyase (from Pseudomonas fluorescens; protein ID (NCBI): AAG02282.1), benzoylformate decarboxylase (from Pseudomonas putida; protein ID (NCBI): AAC15502.1), pyruvate decarboxylase (from Saccharomyces cerevisiae; protein ID (NCBI): CAA39398.1 and from Zymomonas mobitis; protein ID (NCBI): AAA27696.2), and PigD (from Serratia marcescens; C. Dresen, PhD Thesis, University of Freiburg, 2008) in combinations with aromatic, aliphatic and olefinic methyl- and trifluoromethyl ketones. No traces of aldehyde-ketone cross-coupling products were found.
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We have tested the recombinant enzymes benzaldehyde lyase (from Pseudomonas fluorescens; protein ID (NCBI): AAG02282.1), benzoylformate decarboxylase (from Pseudomonas putida; protein ID (NCBI): AAC15502.1), pyruvate decarboxylase (from Saccharomyces cerevisiae; protein ID (NCBI): CAA39398.1 and from Zymomonas mobitis; protein ID (NCBI): AAA27696.2), and PigD (from Serratia marcescens; C. Dresen, PhD Thesis, University of Freiburg, 2008) in combinations with aromatic, aliphatic and olefinic methyl- and trifluoromethyl ketones. No traces of aldehyde-ketone cross-coupling products were found.
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0001167066
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Two-step synthesis: 1 hydroboration of 3,4-dihydro-2H-pyran, according to
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Two-step synthesis: 1) hydroboration of 3,4-dihydro-2H-pyran, according to: H. C. Brown, J. V. N. Vara Prasad, S.-H. Zee, J. Org. Chem. 1985, 50,1582;
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84989478646
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oxidation of tetrahydro-2H-pyran3-ol, according to
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oxidation of tetrahydro-2H-pyran3-ol, according to: A. J. Mancuso, D. Swern et al., Synthesis 1981, 165.
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85036748718
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Compounds 7-10 were prepared by Williamson ether synthesis using the phenols or thiophenol and chloroacetone as reactants.
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Compounds 7-10 were prepared by Williamson ether synthesis using the phenols or thiophenol and chloroacetone as reactants.
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CCDC 752572 (7a), and CCDC 752573 (13a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data- request/cif
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CCDC 752572 (7a), and CCDC 752573 (13a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data- request/cif
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