Use of biological systems for the synthesis of chiral molecules. 5. Microbiological reduction of acyclic .beta.-diketones

Fauve, A.; Veschambre, H.

doi:10.1021/jo00257a004

Cited by 63 publications

(22 citation statements)

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“…(3R)-( -)-3-hydroxy-5-keto and (5R)-( -)-5-hydroxy-3-keto compounds have already been described (Fauve and Veschambre, 1988). …”

Section: Hydroxy Keto Compoundsmentioning

confidence: 96%

“…2-hydroxy-4-keto compounds obtained in this study have already been described (Bolte, Gourcy and Veschambre, 1986;Fauve and Veschambre, 1988).…”

Section: Hydroxy Keto Compoundsmentioning

confidence: 99%

“…We have already reported on the use of biological systems to enantiospecifically reduce various ketones (Belan et al, 1987) and diones (Bolte, Gourcy and Veschambre, 1986;Fauve and Veschambre, 1988). Various microorganisms have been used to obtain some of the possible isomers of the reduction products.…”

Section: Introductionmentioning

confidence: 99%

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Regiospecificity and Enantiospecificity in Microbiological Reduction of Acyclic β-Diketones

Fauve

Veschambre

1990

Biocatalysis

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A screening of microorganisms has been performed to study the regio-and stereospecificities of the reduction of carbonyl groups in 2,4 and 3,5 diketones to obtain all stereoisomers. (2S), (2R), (3S), (3R) and (5R) ketols are obtained along with (2S, 4s) and (3S, 5s) diols often in high optical yields. Chemo-enzymatic methodologies to obtain stereoisomers not reached by direct microbiological reduction are discussed.KEY WORDS Microbiological reduction, acyclic /3-diketones, chiral ketols and diols.Biocatal Biotransformation Downloaded from informahealthcare.com by University of Toronto on 11/05/14For personal use only. 96 A. FAUVE AND H. VESCHAMBREcarried out with a 50 m X 0.32 mm Chrompack column filled with 20% Carbowax and with helium as carrier gas at 1-2 kg/cm2. Measurements of enantiomeric excesses were made by using a 26 m x 0.22 mm Chrompack column filled with Chirasil-L-Valine. Conversion yields and enantiomeric excesses were determined with a Shimadzu CR 3A integrator. Column chromatography was performed on Amicon silica gel (70-200 Mesh) with pentanefether as eluent: 90/10 v/v for ketols and 50/50 v/v for diols.Pentane-2,Cdione was a commercial product. Hexane-2 ,Cdione and octane-3,5-dione were prepared according to Adams (Adams and Hauser, 1944) from acetone and ethylpropionate and butane-2-one and ethylbutyrate respectively.No elemental analyses were performed. As the products obtained have already been described, analysis of their retention times, NMR spectra and optical rotation values were considered as sufficient for identification.'H NMR spectra were recorded on Jeol CX 60 and Bruker 300 MSL at 60 MHz and 300 MHz respectively in CDCI, solutions.Optical rotation values were determined on a Perkin-Elmer 141 polarimeter at 25°C in CHC13 and for the mercury J line ( A = 578 nm). Concentrations are given in g/ml.

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“…(3R)-( -)-3-hydroxy-5-keto and (5R)-( -)-5-hydroxy-3-keto compounds have already been described (Fauve and Veschambre, 1988). …”

Section: Hydroxy Keto Compoundsmentioning

confidence: 96%

“…2-hydroxy-4-keto compounds obtained in this study have already been described (Bolte, Gourcy and Veschambre, 1986;Fauve and Veschambre, 1988).…”

Section: Hydroxy Keto Compoundsmentioning

confidence: 99%

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Regiospecificity and Enantiospecificity in Microbiological Reduction of Acyclic β-Diketones

Fauve

Veschambre

1990

Biocatalysis

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“…An effective way to improve stereoselectivity of the reduction process was the introduction of a sterically demanding sulfur-containing group [208,209]. Acyclic 1,3-and 1,4-diketones gave only poor results; their reduction proceeded slowly but is incomplete, and often the de and ee values were only moderate [210][211][212][213]. An excellent result, however, was achieved for the reduction of 2,5-hexanedione YY255 (Figure 21.14); upon treatment of 46 with baker's yeast (Budweiser) for 144 h a 55% yield of 47 was obtained [214].…”

Section: Figure 2110mentioning

confidence: 99%

Yeast‐Mediated Stereoselective Synthesis

Csük

2016

Green Biocatalysis

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“…A evidência para o isômero-E foi baseada na comparação do espectro de 13 C NMR da mistura de isômeros-Z e E, com uma amostra pura do isômero-E 37 . A redução dos racematos de α-halo e α-azidopropiofenonas mediadas por fermento de pão produzem uma mistura dos diastereoisômeros syn e anti de haloidrinas oticamente ativas como mostrado na Tabela 2 20 .…”

Section: Esquemaunclassified

Reduções enantiosseletivas de cetonas utilizando-se fermento de pão

Rodrigues¹,

Moran²

2001

Quím. Nova

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Use of biological systems for the synthesis of chiral molecules. 5. Microbiological reduction of acyclic .beta.-diketones

Cited by 63 publications

References 0 publications

Regiospecificity and Enantiospecificity in Microbiological Reduction of Acyclic β-Diketones

Regiospecificity and Enantiospecificity in Microbiological Reduction of Acyclic β-Diketones

Yeast‐Mediated Stereoselective Synthesis

Reduções enantiosseletivas de cetonas utilizando-se fermento de pão

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