Optimisation of the bioreduction process of carbonyl compounds promoted by seeds of glossy privet ( Ligustrum lucidum - Oleaceae) and its application to the synthesis of key intermediates

BORDÓN, DANIELA L.; VÁZQUEZ, ANA M.; DECARLINI, MARÍA F.; DEMMEL, GABRIELA I.; ROSSI, LAURA I.; AIMAR, MARIO L.

BIOCATALYSIS AND BIOTRANSFORMATION

TAYLOR & FRANCIS LTD

Año: 2021 vol. 39 p. 1 - 15

1024-2422

The fruits of Ligustrum lucidum were used as an efficient biological reducer of carbonyl compounds,and trials were carried out to optimise the reductive process using acetophenone asthe model substrate. In order to try to eliminate the dependence on the seasonal production ofthe fruits, a study was carried out to find ways to conserve them. The results reported hereshow that it is possible to store the dehydrated fruits of glossy privet at room temperature overa prolonged period of time, during which time they can be used as a common chemicalreagent. On the other hand, studies performed on different parts of the fruits established thatthe seeds are responsible for the bioreduction process, with the best reduction conditions foundbeing isolated seeds from the fruits of glossy privet at 25 C, in a 100mM phosphate buffer pH6.0, using 0.67% w/v of DMSO as co-solvent with an acetophenone charge of 2.67 g/L (22mM).Moreover, seed reuse studies showed that it is possible to recycle them, providing almost thesame activity and enantioselectivity from the first to the fifth cycle, without any loss of biocatalyticproperties. Finally, using whole seeds of glossy privet in optimal reaction conditions,important alcohols useful as key intermediates in the synthesis of industrial products wereobtained on a laboratory scale through the reduction of specially selected ketonesand aldehydes.