Reduction of phenylketones by immobilized baker's yeast

Sorillha, Ana E.P.M.; Marques, Maria Risoleta Freire; Joekes, Inés; José, Paulo; Moran, Samenho; Augusto, Jorge; Rodrigues, Rodney Alexandre Ferreira

doi:10.1016/s0960-894x(01)80448-0

Cited by 33 publications

(3 citation statements)

References 24 publications

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“…α-Dicarbonyl compounds have been the subject of extensive research due to their important applications. − 1-Phenyl-1,2-propanedione (PPD) receives practical use as photosensitizer for photopolymerization of visible light-cured dental resin composites − and as photoinitiator for the photo-cross-linking of waterborne latex paints, being also a common reactant in asymmetric synthesis. − Enantioselective hydrogenation of PPD has been used for production of α-hydroxy carbonyl compounds and diols, − which are utilized in the synthesis of many biologically relevant substances, such as, for example, ephedrine and pseudoephedrine. − The conditions to carry out this reaction have been the matter of several reports: it has been performed using heterogeneous catalysis in different solvents, oxygenation conditions and in the presence or absence of ultrasonic irradiation, − by using bakers yeast as reducing agent, − …”

Section: Introductionmentioning

confidence: 99%

Conformational Flexibility, UV−Induced Decarbonylation, and FTIR Spectra of 1-Phenyl-1,2 Propanedione in Solid Xenon and in the Low Temperature Amorphous Phase

et al. 2005

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1-Phenyl-1,2-propanedione has been isolated in low-temperature xenon matrixes and studied by FTIR spectroscopy, supported by DFT(B3LYP)/6-311++G(d,p) calculations. In good agreement with previous electron diffraction data [Shen, Q.; Hagen, K. J. Phys. Chem. 1993, 97, 985], the calculations predicted the existence of only one stable conformation for the compound, in which the O=C-C=O dihedral angle is 135.6 degrees. On the other hand, the experimental data clearly reveals that, in the as-deposited xenon matrixes (T = 20 K), there is a distribution of molecules with different O=C-C=O dihedral angles around the equilibrium value. This distribution results from the efficient trapping of the conformational distribution existing in the gas phase, prior to deposition, which is determined by the low frequency, large amplitude torsional vibration around the C-C central bond. Upon annealing to higher temperatures (T approximately 45 K), the initially trapped conformational distribution can be modified in a certain degree, favoring more polar structures (corresponding to smaller O=C-C=O dihedral angles), as a result of the interactions with the matrix media. Irradiation of the matrix with UV light (lambda > 235 nm) led to decarbonylation of the compound, with generation of acetophenone and carbon monoxide, with an almost complete consumption of the reagent after 1100 min of irradiation (k = 2.8 x 10(-2) min.(-1)). Aggregation of the compound resulting from the matrix warming was also investigated, providing useful information for interpretation of the spectroscopic data obtained for the low-temperature amorphous state of the neat compound.

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Section: Introductionmentioning

confidence: 99%

Conformational Flexibility, UV−Induced Decarbonylation, and FTIR Spectra of 1-Phenyl-1,2 Propanedione in Solid Xenon and in the Low Temperature Amorphous Phase

et al. 2005

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“…The reduction of 1phenyl-1,2-propanediones (3) mediated by S. cerevisiae was studied by several authors, giving (1R,2S)-1 through intermediates (S)-2 and (R)-1-phenyl-1-hydroxy-2-propanone [(R)-4] (Scheme 1). [19][20][21][22][23][24][25] However, to the best of our knowledge, the bio-oxidation of 1 mediated by resting cells of the above microorganisms has not been published yet.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Oxidation of 1‐Phenyl‐1,2‐propanediol Mediated by Microorganisms

et al. 2011

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The enantioselective oxidation of (1R,2S)‐1‐phenyl‐1,2‐propanediol [(1R,2S)‐1], mediated by baker’s yeast, gave (−)‐(S)‐1‐phenyl‐2‐hydroxy‐1‐propanone [(S)‐2] in 64 % isolated yield and 93 % ee. Kinetic experiments of the bio‐oxidation of (±)‐anti‐1 revealed that the enantiomer (1R,2S)‐1 was more reactive than (1S,2R)‐1. Therefore, this result allowed us to devise a kinetic resolution experiment to obtain (1S,2R)‐1 in >99 % ee from (±)‐anti‐1. The preparation of (1S,2R)‐1 is interesting, as it is the antipode of the product obtained by the reduction of 1‐phenyl‐1,2‐propanedione using baker’s yeast. Other microorganisms, such as Micrococcus luteus, Candida albicans, and Geotrichum candidum, were also used for kinetic resolution experiments of (±)‐anti‐1. The best result was obtained using Geotrichum candidum, which gave (1S,2R)‐1 in 32 % yield and 99 % ee.

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“…The dehydrogenases in the form of whole cells for the production of chiral styrene oxides have been used on a pilot-plant scale [ 4 ]. Therefore, a large number of papers have appeared reporting the enantiomeric reduction of α -bromoacetophenone [ 5 – 10 ] and α -chloroacetophenone [ 4 , 6 , 7 , 11 – 17 ] by whole cells of microorganism and also by isolated enzyme [ 18 ] giving halohydrins in high enantiomeric excesses (ee).…”

Section: Introductionmentioning

confidence: 99%

Chiral Pharmaceutical Intermediaries Obtained by Reduction of 2-Halo-1-(4-substituted phenyl)-ethanones Mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182

2011

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Enantioselective reductions of p-R1-C6H4C(O)CH2R2 (R1 = Cl, Br, CH3, OCH3, NO2 and R2 = Br, Cl) mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182 afforded the corresponding halohydrins with complementary R and S configurations, respectively, in excellent yield and enantiomeric excesses. The obtained (R)- or (S)-halohydrins are important building blocks in chemical and pharmaceutical industries.

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Reduction of phenylketones by immobilized baker's yeast

Cited by 33 publications

References 24 publications

Conformational Flexibility, UV−Induced Decarbonylation, and FTIR Spectra of 1-Phenyl-1,2 Propanedione in Solid Xenon and in the Low Temperature Amorphous Phase

Conformational Flexibility, UV−Induced Decarbonylation, and FTIR Spectra of 1-Phenyl-1,2 Propanedione in Solid Xenon and in the Low Temperature Amorphous Phase

Stereoselective Oxidation of 1‐Phenyl‐1,2‐propanediol Mediated by Microorganisms

Chiral Pharmaceutical Intermediaries Obtained by Reduction of 2-Halo-1-(4-substituted phenyl)-ethanones Mediated by Geotrichum candidum CCT 1205 and Rhodotorula glutinis CCT 2182

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