The asymmetric C-C bond formation is one of the main goals in the synthetic organic chemistry and represents the critical step of many synthesis. Biocatalytic approaches to carboligation are often based on the use of thiamine diphosphate-dependent enzymes and among these acetylacetoin synthase (AAS) is a TDP-depending enzyme playing a key role in the bacterial metabolic pathway known as butanediol cycle. In this cycle, AAS catalyses the condensation reaction between two molecules of 2,3-butanedione (diacetyl) leading to the formation of 3-hydroxy-3-methyl-2,4-pentanedione (acetylacetoin) and acetic acid. Till today very few data regarding the purification and characterization of this enzyme have been reported and AAS has never been employed for synthetic purposes. In the present communication a partial purification of AAS from B. stearothermophilus and its use as catalyst for the conversion of 1,2-diketones to the corresponding 2-alkyl-2-hydroxy -1,3-diketones is described.
Bacillus stearothermophilus acetylacetoin synthase in synthesis of 2-alkyl-2-hydroxy-1,3-diketones
MEDICI, Alessandro;PEDRINI, Paola;VENTURI, Valentina;GIOVANNINI, Pier Paolo
2009
Abstract
The asymmetric C-C bond formation is one of the main goals in the synthetic organic chemistry and represents the critical step of many synthesis. Biocatalytic approaches to carboligation are often based on the use of thiamine diphosphate-dependent enzymes and among these acetylacetoin synthase (AAS) is a TDP-depending enzyme playing a key role in the bacterial metabolic pathway known as butanediol cycle. In this cycle, AAS catalyses the condensation reaction between two molecules of 2,3-butanedione (diacetyl) leading to the formation of 3-hydroxy-3-methyl-2,4-pentanedione (acetylacetoin) and acetic acid. Till today very few data regarding the purification and characterization of this enzyme have been reported and AAS has never been employed for synthetic purposes. In the present communication a partial purification of AAS from B. stearothermophilus and its use as catalyst for the conversion of 1,2-diketones to the corresponding 2-alkyl-2-hydroxy -1,3-diketones is described.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
