Product stereospecificity in the microbial reduction of imidazol-1-yl methyl aryl ketones

Lis, Randall; Caldwell, Walton B.; Rudd, G.; Lumma, William C.; Hoyer, G.‐A.; Petzoldt, Karl; Cleve, Gerhard; Sauer, Gerhard

doi:10.1016/s0040-4039(01)81022-4

Cited by 6 publications

(1 citation statement)

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“…Davis and co-workers have demonstrated product stereospecificity with respect to ketone reduction of pentoxy fylline and warfarin with Rhodotorula rubra and Nocardia corallina, respectively (Davis and Rizzo 1982;Davis et al 1984). In addition, enantioselectivity has been observed in microbial transformation of the following substrates : acetyldimethylphenyl silane (Syldatk et al 1987), ethyl 2acyloxy-3-oxobutanoate (Sakai et al 1986), imidazol-l-ylmethylaryl ketones (Lis et al 1987), pantoyl lactone (Shimizu et al 1987), organometallic aldehydes (Yamazaki and Hosono 1989) and 2-arylpropionic acids (Hutt et a/. 1993).…”

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Microbial metabolism of 2‐arylpropionic acids: effect of environment on the metabolism of ibuprofen by Verticillium lecanii

Hanlon

Kooloobandi

Hutt

1994

Journal of Applied Bacteriology

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The effect of environment on the growth of Verticillium lecanii and its metabolic transformation of racemic ibuprofen are reported. The growth of V. lecanii exhibited a lag phase of up to 12 h followed by a period of rapid growth for up to 4 d. The optimal conditions for growth of the micro‐organism were determined to be 24°C at pH 7.0 with a culture volume of up to one‐tenth of the culture flask volume. The metabolic oxidation of (R,S)‐ibuprofen occurred in both growing cultures and washed cell suspensions of V. lecanii. Examination of the stereochemical composition of the remaining substrate indicated that under both conditions the oxidation was substrate stereoselective for the R‐enantiomer of the drug. Using growing cultures of the micro‐organism, quantitative conversion of the substrate to the metabolite was achieved following incubation for 14 d. Examination of the enantiomeric composition of the metabolic product indicated an excess of the S‐isomer (ratio S/R = 2.1). The possible mechanisms for the apparent anomaly in the stereoselectivity of (R,S)‐ibuprofen metabolism and the enantiomeric composition of the metabolite are discussed.

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