Biocatalytic synthesis of S(−)-1-(1′-naphthyl) ethanol by a novel isolate of Candida viswanathii

Kamble, Ashwini; Soni, Prashant; Banerjee, Uttam Chand

doi:10.1016/j.molcatb.2005.04.012

Cited by 35 publications

(20 citation statements)

References 15 publications

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“…We further discovered a very interesting activation property of IL 1-PS: the acceleration of the rate was significantly dependent on the substrates (Table 4). A truly remarkable acceleration was accomplished for 1 a, 1 b, 1 d, [29] 1 e, [30] 1 h, [33] 1 k, [36] and 1 i; [35] 1100-fold acceleration was obtained for alcohol, (AE ) 32] and 1 j, [35] and none was observed for 1 c [28] or 1 f. [31] The effect of IL 1 on the enantioselectivity was also dependent on the substrate: a remarkably increased enantioselectivity was obtained for 1 a, 1 j, and 1 l, while only a small modification occurred for 1 b.…”

Section: Full Paper Tion Was Recorded (Entry 9) It Is Interesting Thmentioning

confidence: 94%

Increased Enantioselectivity and Remarkable Acceleration of Lipase‐Catalyzed Transesterification by Using an Imidazolium PEG–Alkyl Sulfate Ionic Liquid

Itoh

Matsushita

Abe

et al. 2006

Chemistry A European J

140

115

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Several types of imidazolium salt ionic liquids were prepared derived from poly(oxyethylene)alkyl sulfate and used as an additive or coating material for lipase-catalyzed transesterification in an organic solvent. A remarkably increased enantioselectivity was obtained when the salt was added at 3-10 mol % versus substrate in the Burkholderia cepacia lipase (lipase PS-C)-catalyzed transesterification of 1-phenylethanol by using vinyl acetate in diisopropyl ether or a hexane solvent system. In particular, a remarkable acceleration was accomplished by the ionic liquid coating with lipase PS in an iPr(2)O solvent system while maintaining excellent enantioselectivity; it reached approximately 500- to 1000-fold acceleration for some substrates with excellent enantioselectivity. A similar acceleration was also observed for IL 1-coated Candida rugosa lipase. MALDI-TOF mass spectrometry experiments of the ionic-liquid-coated lipase PS suggest that ionic liquid binds with lipase protein.

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Section: Full Paper Tion Was Recorded (Entry 9) It Is Interesting Thmentioning

confidence: 94%

Increased Enantioselectivity and Remarkable Acceleration of Lipase‐Catalyzed Transesterification by Using an Imidazolium PEG–Alkyl Sulfate Ionic Liquid

Itoh

Matsushita

Abe

et al. 2006

Chemistry A European J

140

115

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“…They display different physical and enzymatic properties, show a wide variety of substrate specificities, and are mainly classified into three superfamilies, zinc-dependent alcohol dehydrogenases, short-chain dehydrogenase/reductases (SDRs), and aldo-keto reductases, based on their catalytic properties and sequence information (8,14,32). Among the various enzyme sources, Candida species are attractive as highly stereospecific oxidoreductase donors (4,13,15,16,25,30). In many cases, the stereospecific oxidoreductases from strains of the genus Candida are dissimilar in structure and classified in different superfamilies (15,16,38).…”

mentioning

confidence: 99%

Purification, Characterization, Gene Cloning, and Expression of a Novel Alcohol Dehydrogenase with Anti-Prelog Stereospecificity from Candida parapsilosis

Nie

et al. 2007

Appl Environ Microbiol

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An alcohol dehydrogenase from Candida parapsilosis CCTCC M203011 was characterized along with its biochemical activity and structural gene. The amino acid sequence shows similarity to those of the short-chain dehydrogenase/reductases but no overall identity to known proteins. This enzyme with unusual stereospecificity catalyzes an anti-Prelog reduction of 2-hydroxyacetophenone to (S)-1-phenyl-1,2-ethanediol.

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“…Moreover, the biological methods are environmentally friendly due to the use of natural resources and complete degradation of biocatalysts after their use. 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.…”

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

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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.

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Biocatalytic synthesis of S(−)-1-(1′-naphthyl) ethanol by a novel isolate of Candida viswanathii

Cited by 35 publications

References 15 publications

Increased Enantioselectivity and Remarkable Acceleration of Lipase‐Catalyzed Transesterification by Using an Imidazolium PEG–Alkyl Sulfate Ionic Liquid

Increased Enantioselectivity and Remarkable Acceleration of Lipase‐Catalyzed Transesterification by Using an Imidazolium PEG–Alkyl Sulfate Ionic Liquid

Purification, Characterization, Gene Cloning, and Expression of a Novel Alcohol Dehydrogenase with Anti-Prelog Stereospecificity from Candida parapsilosis

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

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