Asymmetric Reduction of Ethyl 2-methyl 3-oxobutanoate by Fungi

Iwamoto, Kenzo; Kuramoto, Takayuki; Izumi, Minoru; Kirihata, Mitsunori; Dohmaru, Takaaki; Yoshizako, Fumiki

doi:10.1271/bbb.64.194

Cited by 7 publications

(1 citation statement)

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“…Genetic engineering of baker's yeast has provided useful whole cell catalysts for the synthesis of the syn (2R ,3S ) and anti (2S ,3S ) a-alkyl-b-hydroxyesters with excellent enantio and diastereoselectivity (Rodriguez et al 2001). Screening of several fungi for the reduction of ethyl-2-methyl-3-oxobutanoate resulted in the formation of the anti (2S ,3S ) product as the major optical isomer, with the exception of Trichoderma koningii , which yielded the anti-Prelog product syn (2S ,3R ) ethyl 2-methyl 3-hydroxybutanoate, with excellent enantioselectivity, but only moderate diastereoselectivity (Iwamoto et al 2000). To our knowledge, there is no example of a whole cell biocatalyst that produces the anti (2R ,3R ) a-alkyl-b-hydroxyester (D; Figure 1).…”

Section: Introductionmentioning

confidence: 99%

A recombinantEscherichia coliexpressing an α-alkyl-β-ketoester reductase with unusual stereoselectivity

Panizza

Onetto

Rodrı́guez

2007

Biocatalysis and Biotransformation

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A recombinant Escherichia coli expressing an a-alkyl-b-ketoester reductase that yields the anti (2R ,3R ) a-alkyl-bhydroxyester as the major product was constructed. The enzyme was identified from genomic libraries of Paucimonas lemoignei, cloned and expressed in E. coli providing a whole cell biocatalyst with novel stereoselectivity. This constitutes the first report on a whole cell biocatalyst for the synthesis of (2R ,3R ) a-alkyl-b-hydroxy-esters.

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Section: Introductionmentioning

confidence: 99%