Asymmetric reduction of ketones with a germinated plant

Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones

“…Unfortunately, the enantioselectivity of this reaction was moderate to low (extremely low for 2-tetralone (23) which led to the formation of practically racemic mixture of alcohols). The substituted 2-tetralones (24)(25)(26)(27) independently of nature and position of substituent in the benzene ring gave alcohols with higher enantiomeric excess (40-53% ee). The similar results was reported on the reduction by Fusarium culmorum [44].…”

“…Many other biocatalysts, such as fungal cells [13][14][15][16][17], bacterial strains [18,19], and even plant organs [3,[20][21][22][23] or edible mushrooms [24] were also employed for the preparation of enantiomerically pure alcohols. Recently, germinated radish sprouts have been used as a new type of biocatalyst for the asymmetric reduction of ketones [25]. The use of the whole microbial or plant cells is particularly advantageous since they do not require costly recycling of cofactors because they are recycled by the cell.…”

Enantioselective reduction of aryl and hetero aryl methyl ketones using plant cell suspension cultures of Vigna radiata

“…When compared to isolated enzymes, whole bacterial, yeast, fungal or plant suspension cells circumvent the use of external cofactors. Reports on the plant cell cultures for the asymmetric reduction of prochiral ketones (Maczka & Mironowicz 2004;Orden et al 2008;Yang et al 2008;Matsuo et al 2008) and keto esters (Baskar et al 2004) are scanty though they have proved to be effective. Hence, we focused on identifying an effective plant cell culture for the preparation of important chiral secondary alcohols starting from the prochiral aryl and hetero aryl ketones.…”

Asymmetric Reduction of Heteroaryl Methyl Ketones Using <i>Daucus carota</i>

“…Chiral heteroaryl alcohols have numerous applications as important intermediates in the synthesis of biological active molecules and also act as chiral ligands/auxiliaries in a number of asymmetric addition reactions [7][8][9]. There are many reports describing synthesis of chiral secondary alcohols using biocatalysts obtained from microbial/different parts of plant tissues [10][11][12].The asymmetric reductions of heteroaryl methyl ketones is a straight forward approach and a large number of chemical and biological methodologies (microbial and plant) are known to produce heterocyclic chiral alcohols of biological interest [13][14][15]. However, most of these processes have limitation in commercial application due to long incubation time, low substrate loading, poor isolated yields and enantioselectivity [16,17].…”