Enantioselective reduction of bromo- and methoxy-acetophenone derivatives using carrot and celeriac enzymatic system

Mączka, Wanda; Mironowicz, Agnieszka

doi:10.1016/j.tetasy.2004.05.033

Cited by 45 publications

(24 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1 and 2). Thus, the electron-withdrawing substituent accelerated the reduction, which is in accordance with the results reported by Yang et al [12], Mączka and Mironowicz [21], Yang et al [23], Nakamura and Matsuda [35], and Mandal et al [43].…”

Section: Reduction Of Acetophenones (1-7)supporting

confidence: 91%

“…Until now, many examples of the reduction of ketones by whole cells of microorganisms, mainly yeast, have been described [3][4][5][6][7][8][9][10][11][12]. Many other biocatalysts, such as fungal cells [13][14][15][16][17], bacterial strains [18,19], and even plant organs [3,[20][21][22][23] or edible mushrooms [24] were also employed for the preparation of enantiomerically pure alcohols. Recently, germinated radish sprouts have been used as a new type of biocatalyst for the asymmetric reduction of ketones [25].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones

Świzdor¹,

Janeczko²,

Dmochowska-Gładysz³

2010

J Ind Microbiol Biotechnol

View full text Add to dashboard Cite

Didymosphaeria igniaria is a promising biocatalyst in asymmetric reductions of prochiral aromatic-aliphatic ketones such as acetonaphthones, acetophenones, and acetylpyridines. The organism converted the substrates mainly to (S)-alcohols. Excellent results in terms of conversion and enantioselectivity (100% yield, >99% ee) were obtained with acetonaphthones. In case of acetyl pyridines, the optical purity of the product depended on the position of the carbonyl group on the pyridine ring and followed the order 2-acetyl ≫ 4-acetyl > 3-acetyl-pyridine. Transformation of o-methoxy-acetophenone gave optically pure (S)-(-)-1-(2-methoxyphenyl)-ethanol in 95% yield. The transformation of para-methyl ketone gave (R)-alcohol (81% ee), whereas para-bromo ketone gave (S)-alcohol (98% ee). Monitoring of the biotransformation of these substrates over time led to the conclusion that for both substrates, non-selective carbonyl group reduction occurred in the first step, followed by selective oxidation of the (R)-isomer of p-bromo-phenylethanol and selective oxidation of the (S)-isomer of p-methyl-phenylethanol. D. igniaria exhibited poor enantioselectivity in the reduction of bicyclic aryl-aliphatic ketones such as 1- and 2-tetralones. Only (S)-5-methoxy-1-tetralol was obtained in optically pure (>99% ee) form.

show abstract

Section: Reduction Of Acetophenones (1-7)supporting

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones

Świzdor¹,

Janeczko²,

Dmochowska-Gładysz³

2010

J Ind Microbiol Biotechnol

View full text Add to dashboard Cite

show abstract

“…Stereoselective reduction of 1-(4-methoxyphenyl)ethanone 1 to (S)-1-(4-methoxyphenyl)ethanol 2 with plant cell cultures and microbial cells were reported (Mazczka and Mironowicz 2004;Salvi et al 1995). Other studies have shown that yields of (S)-alcohol were disappointingly low, and most of the biocatalysts afforded relatively low product enantiopure in aqueous systems, possibly resulting from the inhibition of the reaction by the substrate or product, or their toxicity to the cells (Lou et al 2009).…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Bioreduction of 1-(4-Methoxyphenyl)ethanone by Whole Cells of Marine-Derived Fungi

et al. 2011

View full text Add to dashboard Cite

Nine strains of marine-derived fungi (Aspergillus sydowii Ce15, A. sydowii Ce19, Aspergillus sclerotiorum CBMAI 849, Bionectria sp. Ce5, Beauveria felina CBMAI 738, Cladosporium cladosporioides CBMAI 857, Mucor racemosus CBMAI 847, Penicillium citrinum CBMAI 1186, and Penicillium miczynskii Gc5) were screened, catalyzing the asymmetric bioreduction of 1-(4-methoxyphenyl)ethanone 1 to its corresponding 1-(4-methoxyphenyl)ethanol 2. A. sydowii Ce15 and Bionectria sp. Ce5 produced the enantiopure (R)-alcohol 2 (>99% ee) in accordance with the anti-Prelog rule and, the fungi B. felina CBMAI 738 (>99% ee) and P. citrinum CBMAI 1186 (69% ee) in accordance with the Prelog rule. Stereoselective bioreduction by whole cells of marine-derived fungi described by us is important for the production of new reductases from marine-derived fungi.

show abstract

“…rapaceum) for 48 h at room temperature and at pH 6.5 and 6.2, respectively. 143 Both the carrot and the celery systems reduced 3-methoxy acetophenone (151) to the (S)-(-)-(3-methoxyphenyl)ethanol (155) in quantitative yield and 98-100% ee. 2-Bromoacetophenone (153) was also converted enantioselectively to the corresponding (S)-(-)-(2-bromophenyl)ethanol (156) with 100% ee but in only 8 and 27% yield, respectively.…”

Section: Chartmentioning

confidence: 99%

“…Bromo derivatives were typically reduced much faster than the corresponding methoxyacetophenone. 143 Other plant species have also been evaluated for their ability to reduce prochiral ketones. Green grams (Phaseolus aureus Roxb.…”

Section: Chartmentioning

confidence: 99%

Vegetables as Chemical Reagents

et al. 2007

View full text Add to dashboard Cite

Biocatalysis is an important adjunct to the chemical armamentarium that organic chemists may bring to bear for the synthesis of important intermediates and finished pharmaceutical and other commercial products. For most of the world however, such catalytic reagents are not an option due to their high cost and import limitations. Recent studies indicate that the use of locally available vegetables may offer an alternative opportunity for countries to investigate their local resources for the effective conduct of key synthetic transformations with significant economic and ecological implications. This review offers a brief overview of the field of microbial and plant biocatalysts, discusses the studies thus far on the use of intact plant materials for conducting synthetic chemical reactions, and considers some opportunities for future development.

show abstract

Enantioselective reduction of bromo- and methoxy-acetophenone derivatives using carrot and celeriac enzymatic system

Cited by 45 publications

References 19 publications

Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones

Didymosphaeria igniaria: a new microorganism useful for the enantioselective reduction of aryl-aliphatic ketones

Stereoselective Bioreduction of 1-(4-Methoxyphenyl)ethanone by Whole Cells of Marine-Derived Fungi

Vegetables as Chemical Reagents

Contact Info

Product

Resources

About