Stereoselective Reduction of Ethyl 4-Chloro-3-Oxobutanoate by a Microbial Aldehyde Reductase in an Organic Solvent-Water Diphasic System.

Abstract:

:Enzyme-catalyzed asymmetric reduction of ethyl 4-chloro-3-oxobutanoate in an organic solvent-water diphasic system was studied. NADPH-dependent aldehyde reductase isolated from Sporobolomyces salmonicolor AKU4429 and glucose dehydrogenase were used as catalysts for reduction of ethyl 4-chloro-3-oxobutanoate and recycling of NADPH, respectively, in this system. In an aqueous system, the substrate was unstable. Inhibition of the reaction and inactivation of the enzymes by the substrate and the product were also observed. An n-butyl acetate-water diphasic system very efficiently overcame these limitations. In a 1,600-ml-1,600-ml scale diphasic reaction, ethyl (R)-4-chloro-3-hydroxybutanoate (0.80 mol; 86% enantiomeric excess) was produced from the corresponding oxoester in a molar yield of 95.4% with an NADPH turnover of 5,500 mol/mol.

journal_name

Appl Environ Microbiol

authors

Shimizu S,Kataoka M,Katoh M,Morikawa T,Miyoshi T,Yamada H

doi

10.1128/AEM.56.8.2374-2377.1990

keywords:

subject

Has Abstract

pub_date

1990-08-01 00:00:00

pages

2374-2377

issue

8

eissn

0099-2240

issn

1098-5336

journal_volume

56

pub_type

杂志文章
  • Active-Site Engineering of ω-Transaminase for Production of Unnatural Amino Acids Carrying a Side Chain Bulkier than an Ethyl Substituent.

    abstract::ω-Transaminase (ω-TA) is a promising enzyme for use in the production of unnatural amino acids from keto acids using cheap amino donors such as isopropylamine. The small substrate-binding pocket of most ω-TAs permits entry of substituents no larger than an ethyl group, which presents a significant challenge to the pre...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.01533-15

    authors: Han SW,Park ES,Dong JY,Shin JS

    更新日期:2015-10-01 00:00:00

  • Mechanism of action of the peptide antibiotic nisin in liposomes and cytochrome c oxidase-containing proteoliposomes.

    abstract::The interaction of the peptide antibiotic nisin with liposomes has been studied. The effect of this interaction was analyzed on the membrane potential (inside negative) and the pH gradient (inside alkaline) in liposomes made from Escherichia coli phosphatidylethanolamine and egg phosphatidylcholine (9:1, wt/wt). The m...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.57.8.2164-2170.1991

    authors: Gao FH,Abee T,Konings WN

    更新日期:1991-08-01 00:00:00

  • Molecular characterization of multidrug-resistant Escherichia coli isolates from Irish cattle farms.

    abstract::This study describes the genotypic characteristics of a collection of 100 multidrug-resistant (MDR) Escherichia coli strains recovered from cattle and the farm environment in Ireland in 2007. The most prevalent antimicrobial resistance identified was to streptomycin (100%), followed by tetracycline (99%), sulfonamides...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.00601-11

    authors: Karczmarczyk M,Walsh C,Slowey R,Leonard N,Fanning S

    更新日期:2011-10-01 00:00:00

  • Cold-adapted alanine dehydrogenases from two antarctic bacterial strains: gene cloning, protein characterization, and comparison with mesophilic and thermophilic counterparts.

    abstract::The genes encoding NAD(+)-dependent alanine dehydrogenases (AlaDHs) (EC 1.4.1.1) from the Antarctic bacterial organisms Shewanella sp. strain Ac10 (SheAlaDH) and Carnobacterium sp. strain St2 (CarAlaDH) were cloned and expressed in Escherichia coli. Of all of the AlaDHs that have been sequenced, SheAlaDH exhibited the...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.65.9.4014-4020.1999

    authors: Galkin A,Kulakova L,Ashida H,Sawa Y,Esaki N

    更新日期:1999-09-01 00:00:00

  • Analysis of the hupSL operon of the nonheterocystous cyanobacterium Lyngbya majuscula CCAP 1446/4: regulation of transcription and expression under a light-dark regimen.

    abstract::This work presents the characterization of an uptake hydrogenase from a marine filamentous nonheterocystous cyanobacterium, Lyngbya majuscula CCAP 1446/4. The structural genes encoding the uptake hydrogenase (hupSL) were isolated and characterized, and regulatory sequences were identified upstream of hupS. In silico a...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.71.8.4567-4576.2005

    authors: Leitão E,Oxelfelt F,Oliveira P,Moradas-Ferreira P,Tamagnini P

    更新日期:2005-08-01 00:00:00

  • Metabolism of both 4-chlorobenzoate and toluene under denitrifying conditions by a constructed bacterial strain.

    abstract::T1, a dentrifying bacterium originally isolated for its ability to grow on toluene, can also metabolize 4-hydroxybenzoate and other aromatic compounds under denitrifying conditions. A cosmid clone carrying the three genes that code for the 4-chlorobenzoate dehalogenase enzyme complex isolated from the aerobic bacteriu...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.60.3.989-995.1994

    authors: Coschigano PW,Häggblom MM,Young LY

    更新日期:1994-03-01 00:00:00

  • Detection and tracking of a novel genetically tagged biological simulant in the environment.

    abstract::A variant of Bacillus thuringiensis subsp. kurstaki containing a single, stable copy of a uniquely amplifiable DNA oligomer integrated into the genome for tracking the fate of biological agents in the environment was developed. The use of genetically tagged spores overcomes the ambiguity of discerning the test materia...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.02006-12

    authors: Emanuel PA,Buckley PE,Sutton TA,Edmonds JM,Bailey AM,Rivers BA,Kim MH,Ginley WJ,Keiser CC,Doherty RW,Kragl FJ,Narayanan FE,Katoski SE,Paikoff S,Leppert SP,Strawbridge JB,VanReenen DR,Biberos SS,Moore D,Phillips DW,

    更新日期:2012-12-01 00:00:00

  • Endophytic colonization of Vitis vinifera L. by plant growth-promoting bacterium Burkholderia sp. strain PsJN.

    abstract::Patterns of colonization of Vitis vinifera L. cv. Chardonnay plantlets by a plant growth-promoting bacterium, Burkholderia sp. strain PsJN, were studied under gnotobiotic conditions. Wild-type strain PsJN and genetically engineered derivatives of this strain tagged with gfp (PsJN::gfp2x) or gusA (PsJN::gusA11) genes w...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.71.4.1685-1693.2005

    authors: Compant S,Reiter B,Sessitsch A,Nowak J,Clément C,Ait Barka E

    更新日期:2005-04-01 00:00:00

  • Analysis of the genome sequence of Lactobacillus gasseri ATCC 33323 reveals the molecular basis of an autochthonous intestinal organism.

    abstract::This study presents the complete genome sequence of Lactobacillus gasseri ATCC 33323, a neotype strain of human origin and a native species found commonly in the gastrointestinal tracts of neonates and adults. The plasmid-free genome was 1,894,360 bp in size and predicted to encode 1,810 genes. The GC content was 35.3...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.00054-08

    authors: Azcarate-Peril MA,Altermann E,Goh YJ,Tallon R,Sanozky-Dawes RB,Pfeiler EA,O'Flaherty S,Buck BL,Dobson A,Duong T,Miller MJ,Barrangou R,Klaenhammer TR

    更新日期:2008-08-01 00:00:00

  • The lantibiotic mersacidin is an autoinducing peptide.

    abstract::The lantibiotic (lanthionine-containing antibiotic) mersacidin is an antimicrobial peptide consisting of 20 amino acids and is produced by Bacillus sp. strain HIL Y-85,54728. The structural gene (mrsA) and the genes for producer self-protection, modification enzymes, transport proteins, and regulator proteins are orga...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.00723-06

    authors: Schmitz S,Hoffmann A,Szekat C,Rudd B,Bierbaum G

    更新日期:2006-11-01 00:00:00

  • Novel Capsular Polysaccharide Loci and New Diagnostic Tools for High-Throughput Capsular Gene Typing in Streptococcus suis.

    abstract::Streptococcus suis is an important pathogen of pigs and may cause serious disease in humans. Serotyping is an important tool for detection and epidemiological studies of S. suis Thirty-three reference serotypes and nine novel cps loci (NCLs) are recognized in S. suis To gain a better understanding of the prevalence an...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.02102-16

    authors: Qiu X,Bai X,Lan R,Zheng H,Xu J

    更新日期:2016-11-21 00:00:00

  • Putative antiparasite defensive system involving ribosomal and nonribosomal oligopeptides in cyanobacteria of the genus Planktothrix.

    abstract::Parasitic chytrid fungi can inflict significant mortality on cyanobacteria but frequently fail to keep cyanobacterial dominance and bloom formation in check. Our study tested whether oligopeptide production, a common feature in many cyanobacteria, can be a defensive mechanism against chytrid parasitism. The study empl...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.03499-12

    authors: Rohrlack T,Christiansen G,Kurmayer R

    更新日期:2013-04-01 00:00:00

  • Use of controlled luciferase expression to monitor chemicals affecting protein synthesis.

    abstract::In this article, we present a new bioluminescent test system for the screening of chemical compounds with an inhibitory effect on protein synthesis. The test is based on the measurement of real-time in vivo light production by Escherichia coli strains expressing different luciferase genes. The eukaryotic lucGR gene fr...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.61.8.2981-2989.1995

    authors: Lampinen J,Virta M,Karp M

    更新日期:1995-08-01 00:00:00

  • Metabolic engineering for L-glutamine overproduction by using DNA gyrase mutations in Escherichia coli.

    abstract::An L-glutamine-overproducing mutant of an Escherichia coli K-12-derived strain was selected from randomly mutagenized cells in the course of L-alanyl-L-glutamine strain development. Genome-wide mutation analysis unveiled a novel mechanism for L-glutamine overproduction in this mutant. Three mutations were identified t...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.03994-12

    authors: Hayashi M,Tabata K

    更新日期:2013-05-01 00:00:00

  • Reduction of Chromate by Desulfovibrio vulgaris and Its c(3) Cytochrome.

    abstract::Washed cell suspensions of Desulfovibrio vulgaris rapidly reduced Cr(VI) to Cr(III) with H(2) as the electron donor. The c(3) cytochrome from this organism functioned as a Cr(VI) reductase. D. vulgaris may have advantages over previously described Cr(VI) reducers for the bioremediation of Cr(VI)-contaminated waters. ...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.60.2.726-728.1994

    authors: Lovley DR,Phillips EJ

    更新日期:1994-02-01 00:00:00

  • Relationship between virulence gene profiles of atypical enteropathogenic Escherichia coli and Shiga toxin-producing E. coli isolates from cattle and sheep in New Zealand.

    abstract::Virulence gene profiles of atypical enteropathogenic Escherichia coli (aEPEC) and Shiga toxin-producing E. coli (STEC) from cattle, sheep, and humans were examined to determine the relationship between pathotypes. Shared virulence factors (intimin, EHEC hemolysin, serine protease, and a type II secretion system) were ...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.02528-09

    authors: Cookson AL,Cao M,Bennett J,Nicol C,Thomson-Carter F,Attwood GT

    更新日期:2010-06-01 00:00:00

  • Isolation, DNA sequence analysis, and mutagenesis of a proline dehydrogenase gene (putA) from Bradyrhizobium japonicum.

    abstract::We report here the cloning and sequencing of the gene for proline dehydrogenase (putA) of Bradyrhizobium japonicum. An open reading frame coding for 1,016 amino acids was identified. The B. japonicum gene codes for a bifunctional protein with proline dehydrogenase and pyrroline-5-carboxylate (P5C) dehydrogenase activi...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.62.1.221-229.1996

    authors: Straub PF,Reynolds PH,Althomsons S,Mett V,Zhu Y,Shearer G,Kohl DH

    更新日期:1996-01-01 00:00:00

  • Utilization of individual cellodextrins by three predominant ruminal cellulolytic bacteria.

    abstract::Growth of the ruminal bacteria Fibrobacter succinogenes S85, Ruminococcus flavefaciens FD-1, and R. albus 7 followed Monod kinetics with respect to concentrations of individual pure cellodextrins (cellobiose, cellotriose, cellotetraose, cellopentaose, and cellohexaose). Under the conditions tested, R. flavefaciens FD-...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.62.3.1084-1088.1996

    authors: Shi Y,Weimer PJ

    更新日期:1996-03-01 00:00:00

  • Promotion of endodontic lesions in rats by a novel extraradicular biofilm model using obturation materials.

    abstract::Although extraradicular biofilm formation is related to refractory periapical periodontitis, the mechanism of extraradicular biofilm development, as well as its effect on periapical lesions, is unknown. Therefore, we aimed to develop an in vivo extraradicular biofilm model in rats and to identify and quantify extrarad...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.00421-14

    authors: Kuremoto K,Noiri Y,Ishimoto T,Yoneda N,Yamamoto R,Maezono H,Nakano T,Hayashi M,Ebisu S

    更新日期:2014-07-01 00:00:00

  • Identification of the polyhydroxyalkanoate (PHA)-specific acetoacetyl coenzyme A reductase among multiple FabG paralogs in Haloarcula hispanica and reconstruction of the PHA biosynthetic pathway in Haloferax volcanii.

    abstract::Genome-wide analysis has revealed abundant FabG (beta-ketoacyl-ACP reductase) paralogs, with uncharacterized biological functions, in several halophilic archaea. In this study, we identified for the first time that the fabG1 gene, but not the other five fabG paralogs, encodes the polyhydroxyalkanoate (PHA)-specific ac...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.00938-09

    authors: Han J,Lu Q,Zhou L,Liu H,Xiang H

    更新日期:2009-10-01 00:00:00

  • TetR-based gene regulation systems for Francisella tularensis.

    abstract::There are a number of genetic tools available for studying Francisella tularensis, the etiological agent of tularemia; however, there is no effective inducible or repressible gene expression system. Here, we describe inducible and repressible gene expression systems for F. tularensis based on the Tet repressor, TetR. ...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.01679-12

    authors: LoVullo ED,Miller CN,Pavelka MS Jr,Kawula TH

    更新日期:2012-10-01 00:00:00

  • Dispersion and transport of Cryptosporidium Oocysts from fecal pats under simulated rainfall events.

    abstract::The dispersion and initial transport of Cryptosporidium oocysts from fecal pats were investigated during artificial rainfall events on intact soil blocks (1,500 by 900 by 300 mm). Rainfall events of 55 mm h(-1) for 30 min and 25 mm h(-1) for 180 min were applied to soil plots with artificial fecal pats seeded with app...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/aem.70.2.1151-1159.2004

    authors: Davies CM,Ferguson CM,Kaucner C,Krogh M,Altavilla N,Deere DA,Ashbolt NJ

    更新日期:2004-02-01 00:00:00

  • Analysis of bacterial detachment from substratum surfaces by the passage of air-liquid interfaces.

    abstract::A theoretical analysis of the detachment of bacteria adhering to substratum surfaces upon the passage of an air-liquid interface is given, together with experimental results for bacterial detachment in the absence and presence of a conditioning film on different substratum surfaces. Bacteria (Streptococcus sobrinus HG...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.67.6.2531-2537.2001

    authors: Gómez-Suárez C,Busscher HJ,van der Mei HC

    更新日期:2001-06-01 00:00:00

  • Discrimination of species in the genus Listeria by Fourier transform infrared spectroscopy and canonical variate analysis.

    abstract::Infrared spectra of type cultures of the six recognized species of the genus Listeria and of Listeria grayi subsp. murrayi were recorded. By use of a library of 59 spectra, comprising at least six replicates of each type, discrimination by canonical variate analysis of the spectral amplitudes allowed all of the spectr...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.61.1.377-378.1995

    authors: Holt C,Hirst D,Sutherland A,MacDonald F

    更新日期:1995-01-01 00:00:00

  • Nitrogen fixation by Vibrio parahaemolyticus and its implications for a new ecological niche.

    abstract::A Vibrio parahaemolyticus strain isolated from the rhizosphere of the ecosystem dominant estuarine grass, Spartina alterniflora, was characterized and shown to carry nifH, the gene encoding the nitrogenase iron protein, and to fix N(2). Nitrogen fixation may contribute substantially to the adaptability, niche breadth,...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.00981-07

    authors: Criminger JD,Hazen TH,Sobecky PA,Lovell CR

    更新日期:2007-09-01 00:00:00

  • Glutathione reductase-mediated synthesis of tellurium-containing nanostructures exhibiting antibacterial properties.

    abstract::Tellurium, a metalloid belonging to group 16 of the periodic table, displays very interesting physical and chemical properties and lately has attracted significant attention for its use in nanotechnology. In this context, the use of microorganisms for synthesizing nanostructures emerges as an eco-friendly and exciting...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.02207-14

    authors: Pugin B,Cornejo FA,Muñoz-Díaz P,Muñoz-Villagrán CM,Vargas-Pérez JI,Arenas FA,Vásquez CC

    更新日期:2014-11-01 00:00:00

  • Marine Vibrio species produce the volatile organic compound acetone.

    abstract::While screening aerobic, heterotrophic marine bacteria for production of volatile organic compounds, we found that a group of isolates produced substantial amounts of acetone. Acetone production was confirmed by gas chromatography, gas chromatography-mass spectrometry, and high-performance liquid chromatography. The m...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.61.1.44-47.1995

    authors: Nemecek-Marshall M,Wojciechowski C,Kuzma J,Silver GM,Fall R

    更新日期:1995-01-01 00:00:00

  • Enhancement of the efficiency of secretion of heterologous lipase in Escherichia coli by directed evolution of the ABC transporter system.

    abstract::The ABC transporter (TliDEF) from Pseudomonas fluorescens SIK W1, which mediated the secretion of a thermostable lipase (TliA) into the extracellular space in Escherichia coli, was engineered using directed evolution (error-prone PCR) to improve its secretion efficiency. TliD mutants with increased secretion efficienc...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.71.7.3468-3474.2005

    authors: Eom GT,Song JK,Ahn JH,Seo YS,Rhee JS

    更新日期:2005-07-01 00:00:00

  • Sulfate Ester Detergent Degradation in Pseudomonas aeruginosa Is Subject to both Positive and Negative Regulation.

    abstract::Bacteria using toxic chemicals, such as detergents, as growth substrates face the challenge of exposing themselves to cell-damaging effects that require protection mechanisms, which demand energy delivered from catabolism of the toxic compound. Thus, adaptations are necessary for ensuring the rapid onset of substrate ...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.01352-19

    authors: Panasia G,Oetermann S,Steinbüchel A,Philipp B

    更新日期:2019-11-14 00:00:00

  • Comparison of cytotoxicity and thin-layer chromatography methods for detection of mycotoxins.

    abstract::Thirty-three standard mycotoxins were assayed by thin-layer chromatography and by cytotoxicity in HEp-2 and Chang cells. Various levels of detection were found. The cytotoxicity test was significantly more sensitive than thin-layer chromatography for the trichothecenes and should be useful for screening extracts from ...

    journal_title:Applied and environmental microbiology

    pub_type: 杂志文章

    doi:10.1128/AEM.46.4.948-950.1983

    authors: Robb J,Norval M

    更新日期:1983-10-01 00:00:00