Plant and soil enantioselective biodegradation of racemic phenoxyalkanoic herbicides.

Abstract:

:The biodegradation of the chiral phenoxyalkanoic herbicides 2-(2,4-dichlorophenoxy)propionic aid (2,4-DP) and 2-(4-chloro-2-methylphenoxy)propionic acid (MCPP) was investigated using enantioselective HPLC and chiroptical detection. Racemic mixtures of 2,4-DP and MCPP were applied to three species of turf grass, four species of broadleaf weeds, and soil. Preferential degradation of the S-(-) enantiomer of each herbicide was observed in most species of broadleaf weeds and soil, while the degradation in all species of grass occurred without enantioselectivity. The biodegradation in all systems appeared to follow pseudo first-order kinetics with the fastest degradation occurring in broadleaf weeds, followed by the grasses. The slowest degradation was observed in soil. The results of this work illustrate the need to characterize both enantiomers of chiral agrochemicals in order to have an accurate understanding of their distribution and fate in the environment.

journal_name

Chirality

journal_title

Chirality

authors

Schneiderheinze JM,Armstrong DW,Berthod A

doi

10.1002/(SICI)1520-636X(1999)11:4<330::AID-CHIR12>

subject

Has Abstract

pub_date

1999-01-01 00:00:00

pages

330-7

issue

4

eissn

0899-0042

issn

1520-636X

pii

10.1002/(SICI)1520-636X(1999)11:4<330::AID-CHIR12>

journal_volume

11

pub_type

杂志文章
  • Two-dimensional separation of [7]helicene enantiomers on Cu(111).

    abstract::The adsorption of heptahelicene, a helically shaped polyaromatic hydrocarbon (C(30)H(18)), on a Cu(111) surface was studied by means of thermal desorption mass spectrometry (TDMS) and low energy electron diffraction (LEED) at temperatures between 130-1,000 K under ultrahigh vacuum (UHV) conditions. The molecule in the...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10006

    authors: Ernst KH,Kuster Y,Fasel R,Müller M,Ellerbeck U

    更新日期:2001-01-01 00:00:00

  • From cosmic chirality to protein structure: Lord Kelvin's legacy.

    abstract::A selection of my work on chirality is sketched in two distinct parts of this lecture. Symmetry and Chirality explains how the discrete symmetries of parity P, time reversal T, and charge conjugation C may be used to characterize the properties of chiral systems. The concepts of true chirality (time-invariant enantiom...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22017

    authors: Barron LD

    更新日期:2012-11-01 00:00:00

  • Investigation of the chiral recognition ability of human carboxylesterase 1 using indomethacin esters.

    abstract::Human carboxylesterase 1 (hCES1) is an enzyme that plays an important role in hydrolysis of pharmaceuticals in the human liver. In this study, elucidation of the chiral recognition ability of hCES1 was attempted using indomethacin esters in which various chiral alcohols were introduced. Indomethacin was condensed with...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23141

    authors: Takahashi M,Takani D,Haba M,Hosokawa M

    更新日期:2020-01-01 00:00:00

  • Enantioselective catalytic reduction of ketoimines with trichlorosilane promoted by readily available chiral Lewis bases.

    abstract::The straightforward synthesis of a series of enantiomerically pure Lewis basic amides by simple condensation of commercially available enantiopure diamines with picolinic acid is reported. These compounds were shown to promote the enantioselective reduction of ketoimines with trichlorosilane. Working with the model su...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20615

    authors: Guizzetti S,Benaglia M,Cozzi F,Rossi S,Celentano G

    更新日期:2009-01-01 00:00:00

  • Absolute configuration and enantiodifferentiation of a hemicryptophane incorporating an azaphosphatrane moiety.

    abstract::The hemicryptophane racemate (±)-1 was optically resolved by semipreparative HPLC on Chiralpak IC column. The absolute configuration of each isolated enantiomer was established from the analysis of their electronic circular dichroism spectra. Enantiodifferentiation of the chiral cationic cage (±)-1 was evidenced in so...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22100

    authors: Payet E,Dimitrov-Raytchev P,Chatelet B,Guy L,Grass S,Lacour J,Dutasta JP,Martinez A

    更新日期:2012-12-01 00:00:00

  • Circular dichroism eigenspectra of polyproline II and β-strand conformers of trialanine in water: Singular value decomposition analysis.

    abstract::Despite that a number of experimental and theoretical investigations have been carried out to determine the structure of trialanine in water, the reported populations of polyproline II (PPII) and β-strand conformers vary and were found to be dependent on which spectroscopic method was used. Such discrepancies are due ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20870

    authors: Oh KI,Lee KK,Park EK,Yoo DG,Hwang GS,Cho M

    更新日期:2010-01-01 00:00:00

  • Ion channels as pharmacologic receptors: the chirality of drug interactions.

    abstract::Ion channels are pharmacologic receptors and as such exhibit stereoselective interactions with drugs. Ion channels are conformationally mobile transmembrane proteins existing in a number of open and closed states. Drug interactions with these different states may differ quantitatively and qualitatively. Stereoselectiv...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/(SICI)1520-636X(1996)8:1<35::AID-CHIR8>3.0

    authors: Triggle DJ

    更新日期:1996-01-01 00:00:00

  • Enantiomer self-disproportionation and chiral stationary phase based selective chiral separation of organic compounds.

    abstract::In modern chromatography, chiral stationary phase (CSP) and enantiomer self-disproportionation (ESD) are new inventions of packing material offer a guarantee for a successful enantiomeric separation. All CSPs were synthesized by chemical bonding of the relevant organic moieties onto a porous parent silica material for...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20917

    authors: Mayani VJ,Abdi SH,Mayani SV,Kim HC,Park SK

    更新日期:2011-04-01 00:00:00

  • Enantiomeric separation and simulation studies of pheniramine, oxybutynin, cetirizine, and brinzolamide chiral drugs on amylose-based columns.

    abstract::Solid phase extraction (SPE)-chiral separation of the important drugs pheniramine, oxybutynin, cetirizine, and brinzolamide was achieved on the C18 cartridge and AmyCoat (150 x 46 mm) and Chiralpak AD (25 cm x 0.46 cm id) chiral columns in human plasma. Pheniramine, oxybutynin, cetirizine, and brinzolamide were resolv...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22276

    authors: Ali I,Al-Othman ZA,Al-Warthan A,Alam SD,Farooqi JA

    更新日期:2014-03-01 00:00:00

  • Improving enantiomeric resolutions by avoiding peak distortion effects in on-line coupled liquid chromatography to gas chromatography.

    abstract::In this work, we study the effect of different variables affecting elution profile distortion on the enantiomeric resolution eventually achievable when working with on-line coupled liquid chromatography to gas chromatography (LC-GC). Specifically, the proposed configuration combines achiral reversed-phase liquid chrom...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23121

    authors: Martínez RM,Barba C,Robredo S,Herraiz M

    更新日期:2019-10-01 00:00:00

  • Synthesis and pharmacological investigation of stereoisomeric muscarines.

    abstract::The synthesis of the eight stereoisomers of muscarine has been efficiently accomplished by utilizing the two enantiomers of lactic esters as starting material. The synthetic strategy is based on a SnCl4-catalyzed addition of allyltrimethylsilane to O-protected lactic aldehydes followed by an iodocyclization process. A...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530040406

    authors: De Amici M,Dallanoce C,De Micheli C,Grana E,Dondi G,Ladinsky H,Schiavi G,Zonta F

    更新日期:1992-01-01 00:00:00

  • Evaluation of "click" binaphthyl chiral stationary phases by liquid chromatography.

    abstract::Two "click" binaphthyl chiral stationary phases were synthesized and evaluated by liquid chromatography. Their structures incorporate S-(-)-1,1'-binaphthyl moiety as the chiral selector and 1,2,3-triazole ring as the spacer. These chiral stationary phases (CSPs) allowed the efficient resolution for a wide range of rac...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22039

    authors: Yu H,Yin C,Jia C,Jin Y,Ke Y,Liang X

    更新日期:2012-05-01 00:00:00

  • Absolute configuration of oplopanone derivatives from Serphidium stenocephalum: ECD spectra of acyclic ketones with front-octant contributions.

    abstract::The electronic circular dichroism (ECD) spectra of two sesquiterpenoids (1 and 2) related to oplopanone, obtained from a methanolic extract of the plant Serphidium stenocephalum (Artemisia stenocephala), were measured and reproduced by means of time-dependent density functional theory (TDDFT) calculations, establishin...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22263

    authors: Shafiq N,Saleem M,Riaz N,Tousif MI,Jabbar A,Tareen RB,Pescitelli G

    更新日期:2014-01-01 00:00:00

  • Stereoselective metabolism of benalaxyl in liver microsomes from rat and rabbit.

    abstract::Benalaxyl (BX), methyl-N-phenylacetyl-N-2,6-xylyl alaninate, is a potent acylanilide fungicide and consist of a pair of enantiomers. The stereoselective metabolism of BX was investigated in rat and rabbit microsomes in vitro. The degradation kinetics and the enantiomer fraction (EF) were determined using normal high-p...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20879

    authors: Zhang P,Zhu W,Dang Z,Shen Z,Xu X,Huang L,Zhou Z

    更新日期:2011-02-01 00:00:00

  • Enantiospecific analysis of 8-prenylnaringenin in biological fluids by liquid-chromatography-electrospray ionization mass spectrometry: application to preclinical pharmacokinetic investigations.

    abstract::8-Prenylnaringenin (8PN) is a naturally occurring bioactive chiral prenylflavonoid found most commonly in the female flowers of hops (Humulus lupulus L.). A stereospecific method of analysis for 8PN in biological fluids is necessary to study the pharmacokinetic disposition of each enantiomer. A novel and simple liquid...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22343

    authors: Martinez SE,Lakowski TM,Davies NM

    更新日期:2014-08-01 00:00:00

  • Paramagnetic 1H-NMR relaxation probes of stereoselectivity in metalloporphyrin catalyzed olefin epoxidation.

    abstract::Enantioselective catalytic epoxidation of olefins is an important problem from both practical and mechanistic points of view. The origins of chiral induction by asymmetric porphyrin and salen complexes were investigated by FT-NMR T1 relaxation techniques. A new chiral vaulted porphyrin (1) that carries (S)-binaphthyl-...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:

    authors: Groves JT,Crowley SJ,Shalyaev KV

    更新日期:1998-01-01 00:00:00

  • Evaluation of the chiral recognition properties and the column performances of three chiral stationary phases based on cellulose for the enantioseparation of six dihydropyridines by high-performance liquid chromatography.

    abstract::Separations of six dihydropyridine enantiomers on three commercially available cellulose-based chiral stationary phases (Chiralcel OD-RH, Chiralpak IB, and Chiralpak IC) were evaluated with high-performance liquid chromatography (HPLC). The best enantioseparation of the six chiral drugs was obtained with a Chiralpak I...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22690

    authors: Yu J,Tang J,Yuan X,Guo X,Zhao L

    更新日期:2017-03-01 00:00:00

  • Enantioselective degradation of warfarin in soils.

    abstract::Environmental enantioselectivity information is important to fate assessment of chiral contaminants. Warfarin, a rodenticide and prescription medicine, is a chiral chemical but used in racemic form. Little is known about its enantioselective behavior in the environment. In this study, enantioselective degradation of w...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.21023

    authors: Lao W,Gan J

    更新日期:2012-01-01 00:00:00

  • Stereoselective intramolecular cyclization to 4-(hydroxymethyl)-3-(1H-indolyl)oxazolidin-2-ones.

    abstract::A simple high-yield three-steps route to optically active 4-hydroxymethyl-3-(1H-indolyl)oxazolidin-2-ones from (S)-glycidol is described. The key intermediates (R)-oxiran-2-ylmethyl 1H-indol-4/-5-ylcarbamates are obtained in high yields from (S)-glycidol. These are readily transformed to oxazolidin-2-ones, very intere...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22003

    authors: Chiummiento L,Funicello M,Tramutola F

    更新日期:2012-04-01 00:00:00

  • Pharmacologic implications of alpha-adrenoreceptor interactive parameters for epinephrine enantiomers in the rat vas deferens.

    abstract::After alkylation of a fraction of the total alpha-adrenoreceptors by phenoxybenzamine in rat vas deferens, the dissociation constants of (-)- and (+)-epinephrine in functional studies were 7 X 10(-7) M and 2 X 10(-5) M, respectively. In the adrenoreceptor-containing tissue fraction, when 3H-labeled WB4101 was used as ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530010106

    authors: Rice PJ,Miller DD,Sokoloski TD,Patil PN

    更新日期:1989-01-01 00:00:00

  • Stereospecific pH-dependent degradation kinetics of R- and S-naproxen-beta-l-O-acyl-glucuronide.

    abstract::The hydrolysis and acyl migration of biosynthetic S-naproxen-beta-l-O-acyl glucuronide (I) and R-naproxen-beta-l-O-acyl glucuronide (II) was followed by HPLC. Nine first-order kinetic rate constants for the hydrolysis and acyl migration between the beta-l-O-acyl glucuronide, its alpha/beta-2, alpha/beta-3-, alpha/beta...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10047

    authors: Mortensen RW,Sidelmann UG,Tjørnelund J,Hansen SH

    更新日期:2002-05-05 00:00:00

  • Highly enantioselective asymmetric autocatalysis of 2-alkenyl- and 2-vinyl-5-pyrimidyl alkanols with significant amplification of enantiomeric excess.

    abstract::2-Alkenyl- and 2-vinyl-5-pyrimidyl alkanols are highly enantioselective asymmetric autocatalysts with significant amplification of enantiomeric excess in the enantioselective addition of diisopropylzinc to 2-alkenyl- and 2-vinylpyrimidine-5-carbaldehydes. Consecutive asymmetric autocatalysis starting from 7% ee increa...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10068

    authors: Sato I,Yanagi T,Soai K

    更新日期:2002-02-01 00:00:00

  • Enhanced efficiency due to the use of achiral additives in the optical resolution of 1-phenylethylamine by its glutaric acid derivative.

    abstract::Racemic 1-phenylethylamine was optically resolved by its own derivative formed with glutaric acid namely (+)-(R)-N-(1-phenylethyl)glutaramic acid. The amide acid resolving agent was synthesized from (+)-(R)-1-phenylethylamine by N-derivatization. The glutaric acid derivative was the next in a homologous series of dica...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20377

    authors: Schindler J,Egressy M,Bereczki L,Pokol G,Fogassy E,Marthi K

    更新日期:2007-03-01 00:00:00

  • The asymmetric synthesis of (R,R)-formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG2000 and water.

    abstract::(R,R)-formoterol was synthesized in seven steps with 4-hydroxyl-3-nitro-acetophenone as the starting material. The key intermediate, the chiral secondary alcohol 4, was prepared via Rh-catalyzed asymmetric transfer hydrogenation with (S,S)-PEGBsDPEN as the ligand and sodium formate as the hydrogen donor under mild con...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20728

    authors: Huang L,Liu J,Shan W,Liu B,Shi A,Li X

    更新日期:2010-02-01 00:00:00

  • Separation and quantitation of (R)- and (S)-atenolol in human plasma and urine using an alpha 1-AGP column.

    abstract::A method for the determination of (R)- and (S)-atenolol in human plasma and urine is described. The enantiomers of atenolol are extracted into dichloromethane containing 3% heptafluorobutanol followed by acetylation with acetic anhydride at 60 degrees C for 2 h. The acetylated enantiomers were separated on a chiral al...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530010306

    authors: Enquist M,Hermansson J

    更新日期:1989-01-01 00:00:00

  • Resolution of enantiomers of novel C2 -symmetric aminobisphosphinic acids via diastereomeric salt formation with quinine.

    abstract::C2 -symmetric N,N-bis(phosphinomethyl)amines were prepared by the thermal reaction of aromatic aldehydes with ammonia and hypophosphorus acid as previously described. Both enantiomers of C2 -symmetric N,N-bis(phosphinomethyl)amine were obtained in a high enantiomeric purity through the diastereomeric salt formation wi...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22391

    authors: Kaboudin B,Faghihi MR,Kazemi F,Yokomatsu T

    更新日期:2015-01-01 00:00:00

  • Separation of Enantiomers of a Phospholipid in Langmuir Monolayers by a New Selector.

    abstract::Chiral discrimination in a racemic mixture of dipalmitoylphosphatidylcholine (DPPC) is induced by a new selector at the water-air interface: L-DPPC is segregated in the condensed phase of a Langmuir monolayer upon interactions with an enantiopure amphiphilic compound. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22508

    authors: Caminati G,Cicchi S,Lascialfari L,Brandi A

    更新日期:2015-11-01 00:00:00

  • First molecules, biological chirality, origin(s) of life.

    abstract::Origin(s) of biological chirality appear(s) to be intimately connected to origin(s) of life. Prebiotic evolution toward these important turning points can be traced back to single chiral molecules. These can be small (monomeric) units as amino acids or monosaccharides or oligomers as oligo-RNA type molecules. Earlier ...

    journal_title:Chirality

    pub_type: 评论,杂志文章

    doi:10.1002/chir.20796

    authors: Caglioti L,Micskei K,Pályi G

    更新日期:2011-01-01 00:00:00

  • Solid-state circular dichroism and hydrogen bonding, part 2: the case of hypothemycin re-investigated.

    abstract::The impact of crystalline forces on the solid-state circular dichroism (CD) spectrum of hypothemycin (), a biologically active molecule extracted from natural sources, has been analyzed by means of time-dependent density functional theory CD calculations. Input structures were extracted from the X-ray geometry of and ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22008

    authors: Pescitelli G

    更新日期:2012-09-01 00:00:00

  • Evaluation of the enantioselectivity of capillary electrokinetic chromatography using ethanediamine-bonded poly (glycidyl methacrylate) microspheres as the pseudostationary phases.

    abstract::In this work, a new capillary electrokinetic chromatography (EKC) approach using ethanediamine-bonded poly (glycidyl methacrylate) (Ami-PGMA) microspheres as pseudostationary phases (PSPs) for enantioseparation with a polysaccharide, chondroitin sulfate E (CSE), as the chiral selector. The CSE@Ami-PGMA EKC system was ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23035

    authors: Sun X,Yu T,Xu G,Du Y,Chen J,Li X

    更新日期:2019-02-01 00:00:00