Asymmetric Bioreduction of a Bulky Ketone: 1-Phenyl-1-(2-phenylthiazol-5-yl)-methanone

Roy, S.; Alexandre, Vanessa; Neuwels, Michel; Texier, Laurence Le

doi:10.1002/1615-4169(200108)343:6/7<738::aid-adsc738>3.3.co;2-u

Cited by 4 publications

(5 citation statements)

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“…Bulky ketones such as bisaryl ketones can be also successfully desymmetrized by means of microbe-catalyzed reductions. For instance, Roy et al have investigated the preparation of ( R )- and ( S )-1-phenyl-1-(2-phenylthiazol-5-yl)-methanol [( R )- and ( S )- 131 ] by enantioselective bioreduction of 1-phenyl-1-(2-phenylthiazol-5-yl)-methanone with whole microbial cells (Scheme ) . A short screening of 38 microbial strains allowed the selection of two suitable yeast strains fulfilling enantiocomplementarity.…”

Section: 1 Reduction Of Ketonesmentioning

confidence: 99%

Enantioselective Enzymatic Desymmetrizations in Organic Synthesis

2004

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Section: 1 Reduction Of Ketonesmentioning

confidence: 99%

Enantioselective Enzymatic Desymmetrizations in Organic Synthesis

2004

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“…For example, optically active 1,2‐diarylethanols are analogs of the anticancer agent combretastatin (Figure ) . Several reports have been published on the asymmetric reduction of such bulky–bulky ketones with whole cells or purified enzymes . The development of a TeSADH mutant that could accommodate a wide scope of substrates is of interest to advance the use of this robust enzyme.…”

Section: Introductionmentioning

confidence: 99%

Expanding the Substrate Specificity of Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase by a Dual Site Mutation

et al. 2018

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Here, we report the asymmetric reduction of selected phenyl‐ring‐containing ketones by various single‐ and dual‐site mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). The further expansion of the size of the substrate binding pocket in the mutant W110A/I86A not only allowed the accommodation of substrates of the single mutants W110A and I86A within the expanded active site but also expanded the substrate range of the enzyme to ketones bearing two sterically demanding groups (bulky–bulky ketones), which are not substrates for the TeSADH single mutants. We also report the regio‐ and enantioselective reduction of diketones with W110A/I86A TeSADH and single TeSADH mutants. The double mutant exhibited dual stereopreference to generate the Prelog products most of the time and the anti‐Prelog products in a few cases.

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“…This type of ketone can be successfully desymmetrized by means of microbe-catalyzed reductions. For instance, Roy et al have investigated the preparation of ( R )- and ( S )-1-phenyl-1-(2-phenylthiazol-5-yl)-methanol [( R )- and ( S )- 224 ] by enantioselective bioreduction of 1-phenyl-1-(2-phenylthiazol-5-yl)-methanone with whole microbial cells (Scheme ) . A short screening of 38 microbial strains allowed the selection of two suitable yeast strains fulfilling enantiocomplementarity.…”

Section: Redox Reactionsmentioning

confidence: 99%

“…For instance, Roy et al have investigated the preparation of (R)and (S)-1-phenyl-1-(2-phenylthiazol-5-yl)-methanol [(R)-and (S)-224] by enantioselective bioreduction of 1-phenyl-1-(2phenylthiazol-5-yl)-methanone with whole microbial cells (Scheme 44). 190 A short screening of 38 microbial strains allowed the selection of two suitable yeast strains fulfilling enantiocomplementarity. Gram-scale preparations of the (S)and (R)-alcohols were achieved in good to high optical purity and high yield using, respectively, Saccharomyces montanus CBS 6772 and Rhodotorula glutinis var.…”

Section: Chemical Reviewsmentioning

confidence: 99%