2008
DOI: 10.1016/j.tetasy.2008.08.005
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Asymmetric anti-Prelog reduction of ketones catalysed by Paracoccus pantotrophus and Comamonas sp. cells via hydrogen transfer

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Cited by 20 publications
(12 citation statements)
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“…Remarkably, among the nine substrates accepted by R. mucilageinosa GIM 2.157, seven were reduced to the corresponding (S)-alcohols following Prelog's rule, while two were reduced to the corresponding (R)-alcohols following the anti-Prelog's rule. To the best of our knowledge, most ketone reductases follow Prelog's rule and usually afford the (S)-alcohols (Prelog 1964), while only a few whole-cell biocatalysts have been reported to be anti-Prelog (R)-specific (Tujigami et al 2001;Gröger et al 2006;Hu and Xu 2006;Lavandera et al 2008;Xiao et al 2009;Brautigam et al 2009). The varied enantioselectivity of strain R. mucilageinosa GIM 2.157 might be due to the presence of different ketone reductases in the cells; such details would be significant for potential industrial applications.…”
Section: Substrate Specificity and Limitationmentioning
confidence: 99%
“…Remarkably, among the nine substrates accepted by R. mucilageinosa GIM 2.157, seven were reduced to the corresponding (S)-alcohols following Prelog's rule, while two were reduced to the corresponding (R)-alcohols following the anti-Prelog's rule. To the best of our knowledge, most ketone reductases follow Prelog's rule and usually afford the (S)-alcohols (Prelog 1964), while only a few whole-cell biocatalysts have been reported to be anti-Prelog (R)-specific (Tujigami et al 2001;Gröger et al 2006;Hu and Xu 2006;Lavandera et al 2008;Xiao et al 2009;Brautigam et al 2009). The varied enantioselectivity of strain R. mucilageinosa GIM 2.157 might be due to the presence of different ketone reductases in the cells; such details would be significant for potential industrial applications.…”
Section: Substrate Specificity and Limitationmentioning
confidence: 99%
“…[44] PpADH was able to reduce chloroketones 5 a-c and displayed an anti-Prelog selectivity (for chlorohydrins 6 a-d, the largest group has the lowest Cahn-Ingold-Prelog (CIP) priority), which gave (S,S)-halohydrins with a higher diastereomeric excesses (de) for substrates with tert-butyloxycarbonyl (Boc; 5 a) and carboxybenzyl (Cbz; 5 b) protecting groups (entries 1 and 2, Table 1) than for the smaller methyloxycarbonyl (Moc) group (5 c; entry 3, Table 1). Anti-Prelog selectivity has been reported for the reduction of ketones by cells of P. pantotrophus, [45] whereas the biocatalyst used here, E. coli whole cells that contain a short-chain alcohol dehydrogenase of P. pantotrophus, [38] was reported previously to reduce ketones with Prelog selectivity, which includes a-chloroacetophenone. Nonetheless, these data were obtained mainly from the reduction of aryl alkyl ketones, which have a low structural similarity with the substrates used in this work.…”
Section: Resultsmentioning
confidence: 84%
“…The resolution of racemates is the most commonly employed in the preparation of chiral compounds (Lavandera et al . ; Cazetta et al . ).…”
Section: Introductionmentioning
confidence: 99%
“…(Turner 2010;Tian et al 2011). The resolution of racemates is the most commonly employed in the preparation of chiral compounds (Lavandera et al 2008;Cazetta et al 2014). Additionally, among the methods, the application of whole-cell oxidizing racemic PED in asymmetry to obtain optical purity of enantiomer has been confirmed.…”
Section: Introductionmentioning
confidence: 99%