Elsevier

Tetrahedron Letters

Volume 41, Issue 35, August 2000, Pages 6799-6802
Tetrahedron Letters

Cyanobacterium-catalyzed asymmetric reduction of ketones

https://doi.org/10.1016/S0040-4039(00)01132-1Get rights and content

Abstract

Synechococcus sp. PCC 7942, a cyanobacterium, acted as a biocatalyst to reduce aryl methyl ketones into the corresponding (S)-alcohols with excellent enantioselectivities under illumination.

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    Cyanobacteria are photoautotrophs capable of harvesting light energy and sequestering CO2, thereby maintaining the redox balance in the cell by recycling NADPH and ATP, via the photosystem (PS) and Calvin cycle (Alagesan et al., 2016, 2013; Hendry et al., 2016; Yamanaka et al., 2011). This light driven synthesis of NADPH has been demonstrated as an efficient system for cofactor recycling during biotransformation using both native and recombinant cyanobacteria (Köninger et al., 2016; Nakamura et al., 2000; Nakamura and Yamanaka, 2002a). While the effect of CO2 in modulating product enantioselectivity has been observed in the conversion of acetophenone in cultures of Nicotiana tabacum, it did not affect the conversion efficiency (Kojima et al., 2009).

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    Nakamura et al. found that Synechococcus sp. PCC7942 had good catalytic activities on perfluoroacetophenone [21], its conversion efficiency was about 95% and e.e. was >99%. They also found the catalytic efficiency of Synechococcus elongates PCC7942 on α,α‑difluoroacetophenone was higher (99%) and e.e. relatively lower (70%) [29].

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