Mikrobielle asymmetrische Katalyse — enantioselektive Reduktion von Ketonen

Sih, Charles J.; Chen, Ching‐Shih

doi:10.1002/ange.19840960806

Cited by 75 publications

(4 citation statements)

References 44 publications

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“…Early investigations of reactions catalyzed by Saccharomyces cerevisiae revealed that the stereochemical course of the reduction of 3-oxoacids is influenced by the chain lengths of the substrates: ( 3-oxobutanoic acid is reduced to (S)-3-hydroxybutanoic acid (13), whereas the reduction of 3-oxohexanoic acid leads to the (R)-configu rated hydroxyacid (14)· Sih et al (15) demonstrated that the optical purities of 3-hydroxyacid esters obtained by yeast catalyzed reduc tion can be controlled by variation of the structures of the educts (e.g. by different chain lengths of acid and alcohol moieties, re spectively, of the 3-oxoacid esters).…”

Section: Oxidoreductases Catalyzing the Enantioselective Reduction Ofmentioning

confidence: 99%

Biosynthesis of Chiral Flavor and Aroma Compounds in Plants and Microorganisms

et al. 1989

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Capillary gas chromatographic determination of optical purities, investigation of the conversion of potential precursors, and characterization of enzymes catalyzing these reactions were applied to study the biogenesis of chiral volatiles in plants and microorganisms. Major pineapple constituents are present as mixtures of enantiomers. Reductions, chain elongation, and hydration were shown to be involved in the biosynthesis of hydroxy acid esters and lactones. Reduction of methyl ketones and subsequent enantioselective metabolization by Penicillium citrinum were studied as model reactions to rationalize ratios of enantiomers of secondary alcohols in natural systems. The formation of optically pure enantiomers of aliphatic secondary alcohols and hydroxy acid esters using oxidoreductases from baker's yeast was demonstrated.The world-wide trend to "natural" flavor and aroma has significantly increased interest in biogenetical pathways leading to volatiles in natural systems. For chiral compounds the exploration of potential biosynthetic routes is even more important, because chemical syntheses are often difficult and expensive; in many cases however sensory qualities of enantiomers are different (1-3). In our current studies of chiral volatiles in plant and microbial systems we use different analytical approaches, (a) Capillary gas chromatographic separations of diastereoisomeric derivatives are used to determine the configurations of chiral constituents at trace levels, (b) Chemically synthesized (labeled) precursors are added to fruit tissues and microorganisms. Their transformation into chiral constituents is investigated by means of capillary gas chromatography/mass spectrometry; the stereochemical course of these metabolizations is followed, (c) Enzymes catalyzing the stereospecific conversion of precursors to chiral compounds are isolated and characterized; commercially available enzymes are investigated as model systems to elucidate the stereochemical course of biogenetical pathways. The combination of these methods revealed some new aspects of the biosynthesis of chiral compounds in natural systems.

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Section: Oxidoreductases Catalyzing the Enantioselective Reduction Ofmentioning

confidence: 99%

Biosynthesis of Chiral Flavor and Aroma Compounds in Plants and Microorganisms

et al. 1989

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“…Furthermore, S. cerevisiae mediated reduction of ethyl-4-azidoacetoacetate and ethyl-4-bromoacetoacetate affords (3R) and (3S) alcohols, respectively, in high optical purity [100]. Thus, S. cerevisiae contains different enzymes acting in accordance to substrate specifity and kinetical properties with opposite stereochemistry [102].…”

Section: L-carnltlnementioning

confidence: 99%

Synthesis of l-carnitine by microorganisms and isolated enzymes

Jung

Kleber

1993

Measurement and Control

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“…Microbial asymmetric ketone reduction as a method for the production of chiral alcohols has been studied extensively (Sih and Chen 1984). The resulting optically pure ot-halohydrins may subsequently be chemically converted into optically pure epoxides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of optically pure 1,2-epoxypropane by microbial asymmetric reduction of chloroacetone

Weijers

Litjens

Bont

1992

Appl Microbiol Biotechnol

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A number of bacteria and yeasts was screened for asymmetric reduction of prochiral chloroacetone into chiral 1-chloro-2-propanol, which is chemically convertible into chiral 1,2-epoxypropane. In this way Rhodotorula glutinis produced optically pure S-1,2epoxypropane with 98°7o enantiomeric excess and in a relatively high final concentration. The enzyme that catalysed the asymmetric reduction was an NAD(P)H-dependent alcohol dehydrogenase. Reduction of racemic 3-chloro-2-butanone resulted in mixtures of cis and trans-2,3-epoxybutane, indicating that no enantioselecrive reduction of this haloketone occurred.

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Mikrobielle asymmetrische Katalyse — enantioselektive Reduktion von Ketonen

Cited by 75 publications

References 44 publications

Biosynthesis of Chiral Flavor and Aroma Compounds in Plants and Microorganisms

Biosynthesis of Chiral Flavor and Aroma Compounds in Plants and Microorganisms

Synthesis of l-carnitine by microorganisms and isolated enzymes

Synthesis of optically pure 1,2-epoxypropane by microbial asymmetric reduction of chloroacetone

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