Abstract
To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral a-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose, the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90%) and good enantioselectivities (60-74%). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.
Highlights
Biotransformation of exogenous substrates have been widely studied and used to prepare chiral compounds
As a part of our ongoing project in the application of novel biocatalysts from the Brazilian biodiversity,[7] we report an investigation of the whole marine sponge C. varians as reducing agent of α-keto esters and isatin (1H-indole2,3‐dione) (1) to the corresponding chiral alcohols
There are several reports available in the literature dealing with stereoselective reduction of ketones and β-keto esters mediated by biocatalysis, the bioreduction of α-keto esters is less common
Summary
Biotransformation of exogenous substrates have been widely studied and used to prepare chiral compounds. As a part of our ongoing project in the application of novel biocatalysts from the Brazilian biodiversity,[7] we report an investigation of the whole marine sponge C. varians as reducing agent of α-keto esters and isatin (1H-indole2,3‐dione) (1) to the corresponding chiral alcohols.
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