Methyl 4-bromo-3-oxobutyrate

Asako et al. found a novel reductase in P. citrinum IF04631 18,52], which could reduce methyl 4-bromo-3-oxobutyrate (BAM) to methyl (S)-4-bromo-3-hydroxybu-tyrate (BHBM), a usefiil pharmaceutical intermediate for the synthesis of HMG-CoA reductase inhibitors as wdl as (S)-4chiral intermediate is much higher than CHBE because of the existence of bromine atom however, BHBM is quite toxic for biocatalysts. Therefore, the enzyme catalyzing the reduction of BAM should possess tolerance toward such compounds. 

Asako, H., Wakita, R., Matsumura, K., Shimizu, M., Sakai, J., and Itoh, N. (2005) Purification and cDNA cloning of NADPH-dependent aldoketoreductase, involved in asymmetric reduction of methyl 4-bromo-3-oxobutyrate, from Penicillium citrinum IF04631. Appl. Environ. Microbiol., 71, 1101-1104. 

Majima et al. prepared ethyl y-(3-indolyl)-y-oxobutyrate (250) in a similar manner by the condensation of the indole Grignard reagent with /3-ellioxycarbonylpropionyl chloride.107 Methyl y-(3-indolyl)-y-oxobutyrate (251) has been obtained by the action of /3-mcthoxycarbonylpropionyl chloride on indole magnesium iodide in ether.118 119 Ballantine et al. prepared methyl y-(5-methoxy-3-indolyl)-y-oxobutyrate 252118 and Julia et al. obtained methyl y-(5-bromo-3-indolyl)-y-oxobutyrate (253)120 by analogous procedures. 

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