We studied an enantioselective lipase-catalysed transesterification reaction for the production of the statin lactone moiety. It is well known that the chiral cyclic structure of statins is very important for their pharmaceutical activity in the prevention and treatment of coronary artery diseases. We focused our attention on 3R,5R-6-(ethyl-2-phenyl)-4-hydroxytetrahydropyran-2-one (2); this was synthesised by employing an enantioselective lactonisation reaction catalysed by a commercial preparation of porcine pancreatic lipase (PPL) starting from a racemic mixture of syn-diol rac-1. Optimisation of the reaction conditions for the biocatalysed intramolecular transesterification reaction of the racemic diol 1 was carried out. It was seen that the maximal reaction rate could be greatly enhanced by the addition of solid matrices to the reaction medium.
Lipase enhanced catalytic efficiency in lactonisation reactions / Carlo, Bonini; Cinzia, Cazzato; Cernia, Enrico; Palocci, Cleofe; Soro, Simonetta; Licia, Viggiani. - In: JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC. - ISSN 1381-1177. - STAMPA. - 16:1(2001), pp. 1-5. [10.1016/s1381-1177(01)00037-6]
Lipase enhanced catalytic efficiency in lactonisation reactions
CERNIA, Enrico;PALOCCI, Cleofe;SORO, Simonetta;
2001
Abstract
We studied an enantioselective lipase-catalysed transesterification reaction for the production of the statin lactone moiety. It is well known that the chiral cyclic structure of statins is very important for their pharmaceutical activity in the prevention and treatment of coronary artery diseases. We focused our attention on 3R,5R-6-(ethyl-2-phenyl)-4-hydroxytetrahydropyran-2-one (2); this was synthesised by employing an enantioselective lactonisation reaction catalysed by a commercial preparation of porcine pancreatic lipase (PPL) starting from a racemic mixture of syn-diol rac-1. Optimisation of the reaction conditions for the biocatalysed intramolecular transesterification reaction of the racemic diol 1 was carried out. It was seen that the maximal reaction rate could be greatly enhanced by the addition of solid matrices to the reaction medium.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
