Enantioselective separation of (±)-β-hydroxy-1,2,3-triazoles by supercritical fluid chromatography and high-performance liquid chromatography.


:This paper reports the enantioseparation of β-hydroxy-1,2,3-triazole derivatives, which present a broad range of biological properties, by supercritical fluid chromatography (SFC) and high-performance liquid chromatography techniques (HPLC). Polysaccharide-based chiral columns (cellulose and amylose) were used to evaluate the separation in SFC and HPLC. Time of analyses, consumption of solvent, and parameter optimization were reduced using SFC technique. The columns based on cellulose chiral stationary phase using 2-propanol and ethanol as modifiers showed the best results for the enantioresolution of the (±)-β-hydroxy-1,2,3-triazoles by SFC analyses. These techniques were applied to evaluate the selectivity of biocatalytic reduction of β-keto-1,2,3-triazoles by marine-derived fungus Penicillium citrinum CBMAI 1186 to obtain the (±)-β-hydroxy-1,2,3-triazoles.






Alvarenga N,Porto ALM,Barreiro JC




Has Abstract


2018-07-01 00:00:00












  • Chiral investigation of midodrine, a long-acting alpha-adrenergic stimulating agent.

    abstract::Midodrine hydrochloride is a peripheral alpha(1)-adrenoreceptor agonist that induces venous and arterial vasoconstriction. Midodrine, after oral or intravenous administration, undergoes enzymatic hydrolysis and releases deglymidodrine, a pharmacologically active metabolite. Midodrine and deglymidodrine have a chiral c...


    pub_type: 杂志文章


    authors: Quaglia MG,Farina A,Palmery M,Desideri N,Donati E,Bossù E,Strano S

    更新日期:2004-07-01 00:00:00

  • Natural alkaloids and synthetic relatives as chiral templates of the Orito's reaction.

    abstract::The enantioselective hydrogenation of methyl or ethyl pyruvate over cinchona-platinum catalyst system (Orito's reaction) is one of the most intensively studied heterogeneous catalytic asymmetric hydrogenation reactions. Studies aiming at systematic changes of the chiral template have played a crucial role in creating ...


    pub_type: 杂志文章,评审


    authors: Tálas E,Margitfalvi JL

    更新日期:2010-01-01 00:00:00

  • Configuration of heptopyranoside and heptofuranoside side chains: 2-anthroate, a powerful chromophore for exciton coupled CD.

    abstract::The absolute configuration of the acyclic side chain of heptopyranosides and heptofuranosides was determined by exciton coupled CD, employing the strongly fluorescent 2-anthroate chromophore. The usage of this chromophore offers significant improvements over previous chemical and spectroscopic procedures since its int...


    pub_type: 杂志文章


    authors: Akritopoulou-Zanze I,Nakanishi K,Stepowska H,Grzeszczyk B,Zamojski A,Berova N

    更新日期:1997-01-01 00:00:00

  • Chirality and chiroptical properties of amyloid fibrils.

    abstract::Chirality of amyloid fibrils-linear beta-sheet-rich aggregates of misfolded protein chains-often manifests in morphological traits such as helical twist visible in atomic force microscopy and in chiroptical properties accessible to vibrational circular dichroism (VCD). According to recent studies the relationship betw...


    pub_type: 杂志文章,评审


    authors: Dzwolak W

    更新日期:2014-09-01 00:00:00

  • (R,R)-N,N'-dimethylcyclohexyl-1,2-diazaseleno-phospholidine as a chiral derivatizing agent for the evaluation of chiral alcohols.

    abstract::Previously, a diazaphospholidine has been synthesized and evaluated as a chiral derivatizing reagent for the determination of the optical purity of chiral alcohols via 31P NMR spectroscopy (Alexakis et al., J. Org. Chem. 57:1224-1237, 1992). Our laboratory is interested in the advantageous and practical applications o...


    pub_type: 杂志文章


    authors: House KL,O'Connor MJ,Silks LA 3rd,Dunlap RB,Odom JD

    更新日期:1994-01-01 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 ...


    pub_type: 评论,杂志文章


    authors: Caglioti L,Micskei K,Pályi G

    更新日期:2011-01-01 00:00:00

  • Enantioselective photoreaction of achiral tropolone ether in inclusion crystals with optically active host compounds.

    abstract::Achiral 4-isopropyltropolone methyl ether (3) included in an optically active host compound (-)-1 yielded optically active photocyclization products (-)-5 and (-)-6 in 96 and 90% ee, respectively, upon photoirradiation in the solid state. ...


    pub_type: 杂志文章


    authors: Tanaka K,Nagahiro R,Urbanczyk-Lipkowska Z

    更新日期:2002-07-01 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 ...


    pub_type: 杂志文章


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

    更新日期:2019-02-01 00:00:00

  • Synthesis of Novel Chiral Sulfonamide-Bearing 1,2,4-Triazole-3-thione Analogs Derived from D- and L-Phenylalanine Esters as Potential Anti-Influenza Agents.

    abstract::Novel enantiopure 1,2,4-trizole-3-thiones containing a benzensulfonamide moiety were synthesized via multistep reaction sequence starting with D-phenylalanine methyl ester and L-phenylalanine ethyl ester as a source of chirality. The chemical structures of all compounds were characterized by elemental analysis, UV, IR...


    pub_type: 杂志文章


    authors: Başaran E,Karaküçük-Iyidoğan A,Schols D,Oruç-Emre EE

    更新日期:2016-06-01 00:00:00

  • Spontaneous resolution of 2,3-bis-fluoren-9-ylidenesuccinic acid induced by achiral guest inclusion.

    abstract::The racemic title host compound (1) formed homochiral inclusion crystals (conglomerate) of 1 with acetone, while heterochiral inclusion crystals (racemate) were obtained when complexed with ethyl acetate. Upon treatment of the homochiral inclusion crystals of 1 with gaseous acetyl chloride in the solid state, opticall...


    pub_type: 杂志文章


    authors: Tanaka K,Iwamoto T,Wada S,Frelek J,Caira MR

    更新日期:2006-08-01 00:00:00

  • Enantioselective and diastereoselective Michael addition of ketone/aldehyde to trans-nitroolefins catalyzed by a novel chiral pyrrolidine-thiourea.

    abstract::The direct Michael addition reaction of cyclohexanone/aliphatic aldehydes with nitroolefins, catalyzed by a novel chiral pyrrolidine-thiourea catalyst 1a, is described. The desired 1,4-adducts were obtained in moderate yields with enantioselectivities up to 99% ee and dr up to 99:1 of the syn product. ...


    pub_type: 杂志文章


    authors: Shen Z,Zhang Y,Jiao C,Li B,Ding J,Zhang Y

    更新日期:2007-05-05 00:00:00

  • Dynorphin A analogs containing a conformationally constrained phenylalanine derivative in position 4: reversal of preferred stereochemistry for opioid receptor affinity and discrimination of kappa vs. delta receptors.

    abstract::Analogs of the opioid peptide [D-Ala8]dynorphin A-(1-11)NH2 containing optically pure (R)- and (S)-2-aminotetralin-2-carboxylic acid (Atc) in position 4 were synthesized and evaluated for opioid receptor affinity. These peptides are the first reported dynorphin A analogs containing a conformationally constrained amino...


    pub_type: 杂志文章


    authors: Aldrich JV,Zheng QI,Murray TF

    更新日期:2001-01-01 00:00:00

  • Lack of metabolic racemisation of ropivacaine, determined by liquid chromatography using a chiral AGP column.

    abstract::Ropivacaine hydrochloride monohydrate (ropivacaine) is a new local anaesthetic agent which is administered exclusively as the (-)-(S)-form. The aim of the study was to determine whether metabolic racemisation of (-)-(S)-ropivacaine occurs. This was tested in man, rat, dog, and sheep after different routes of administr...


    pub_type: 杂志文章


    authors: Arvidsson T,Bruce HF,Halldin MM

    更新日期:1995-01-01 00:00:00

  • Nonlinear chiral interactions in resolutions with benzylamine derivatives.

    abstract::N-formylphenylalanine was subjected to optical resolution using a chiral agent such as phenylethylamine enantiomer, (R)-phenylglycine methyl ester, (S)-N-benzyl-2-aminobutanol, alone or in a mixture with each other or in a mixture with benzylamine. ...


    pub_type: 杂志文章


    authors: Pálovics E,Fogassy E,Schindler J,Nógrádi M

    更新日期:2007-01-01 00:00:00

  • Spectroscopic, Structural, and Computational Characterization of Three Bispidinone Derivatives, as Ligands for Enantioselective Metal Catalyzed Reactions.

    abstract::Three chiral derivatives of the alkaloid sparteine (bispidines), characterized by the 3,7-diazabicyclo[3.3.1]nonane moiety, were designed as efficient ligands in a number of enantioselective reactions due to their metal coordination properties. A full evaluation of the 3D properties of the compounds was carried out, a...


    pub_type: 杂志文章


    authors: Castellano C,Sacchetti A,Meneghetti F

    更新日期:2016-04-01 00:00:00

  • Headspace gas chromatography-mass spectrometry analysis of isoflurane enantiomers in blood samples after anesthesia with the racemic mixture.

    abstract::Several in vivo and in vitro studies on the stereoselective potency of isoflurane enantiomers suggest beneficial effects of the (+)-(S)-enantiomer. In order to detect possible differences in the pharmacokinetics of isoflurane enantiomers, a clinical study of 41 patients undergoing general anesthesia maintained with ra...


    pub_type: 临床试验,杂志文章


    authors: Schmidt R,Wahl HG,Häberle H,Dieterich HJ,Schurig V

    更新日期:1999-01-01 00:00:00

  • Chiral discrimination of the analgesic cizolirtine by using cyclodextrins: A (1)H NMR study on the solution structures of their host-guest complexes.

    abstract::The use of four cyclodextrins (three native and one beta-CD derivative) as NMR chiral solvating agents to resolve the enantiomers of (+/-)-cizolirtine, 1, and its chemical precursor (the carbinol, (+/-)-2), was investigated. The best enantiodiscrimination occurred when beta-cyclodextrin was used. ROESY experiments wer...


    pub_type: 杂志文章


    authors: Redondo J,Blázquez MA,Torrens A

    更新日期:1999-01-01 00:00:00

  • Chiroptical properties of 2,2'-bioxirane.

    abstract::The two enantiomers of 2,2'-bioxirane were synthesized, and their chiroptical properties were thoroughly investigated in various solvents by polarimetry, vibrational circular dichroism (VCD), and Raman optical activity (ROA). Density functional theory (DFT) calculations at the B3LYP/aug-cc-pVTZ level revealed the pres...


    pub_type: 杂志文章


    authors: Daugey N,De Rycke N,Brotin T,Buffeteau T

    更新日期:2018-04-01 00:00:00

  • Metabolic chiral inversion of ibuprofen in isolated rat hepatocytes.

    abstract::Ibuprofen was used to demonstrate that isolated rat hepatocytes offer a suitable in vitro model to investigate the metabolic chiral inversion of anti-inflammatory 2-arylpropionic acids (profens). The inversion of the pharmacologically inactive (-)-(R)-ibuprofen to the active (+)-(S)-ibuprofen was shown to obey apparen...


    pub_type: 杂志文章


    authors: Müller S,Mayer JM,Etter JC,Testa B

    更新日期:1990-01-01 00:00:00

  • CHIRBASE, a graphical molecular database on the separation of enantiomers by liquid-, supercritical fluid-, and gas chromatography.

    abstract::In order to cope with the increasing number of publications on the separation of enantiomers by chromatography on a chiral stationary phase, the graphical molecular database CHIRBASE was created. In the present state, the database package covers information (structural, bibliographic, and chromatographic data) on liqu...


    pub_type: 杂志文章


    authors: Koppenhoefer B,Nothdurft A,Pierrot-Sanders J,Piras P,Popescu C,Roussel C,Stiebler M,Trettin U

    更新日期:1993-01-01 00:00:00

  • Species differences in the generation of the chiral sulfoxide metabolite of albendazole in sheep and rats.

    abstract::The prochiral anthelmintic drug albendazole was administered orally to sheep and rats. Blood samples were taken at standardized intervals during the time course of the plasma kinetics: 18 h in rats and 48 h in sheep. The enantiomeric ratio of the sulfoxide metabolite was determined by means of HPLC on a chiral station...


    pub_type: 杂志文章


    authors: Delatour P,Benoit E,Caude M,Tambute A

    更新日期:1990-01-01 00:00:00

  • Stereoselective renal secretion of carbenicillin in rabbits: role of the organic anion transporter at the renal brush border membrane.

    abstract::Stereoselectivity in the renal secretion of carbenicillin (CBPC) was studied in rabbits. Significant renal secretion of CBPC was observed in vivo, with the secretion of the S-epimer being greater than that of the R-epimer. Stereoselective transport of CBPC was further studied in vitro using basolateral and brush borde...


    pub_type: 杂志文章


    authors: Itoh T,Nakaura H,Koyano S,Tsuda Y,Yamada H

    更新日期:1998-01-01 00:00:00

  • Copper(II) complexes of N2-alkyl-(S)-amino acid amides as chiral selectors for dynamically coated chiral stationary phases in RP-HPLC.

    abstract::Copper(II) complexes of N2-octyl-(S)-phenylalaninamide (Noc-Phe-NH2), N2-dodecyl-(S)-phenylalaninamide (Ndo-Phe-NH2), and N2-octyl-(S)-norleucinamide (Noc-NLeu-NH2), dynamically adsorbed on a reversed-phase C18 column, were able to perform the direct enantiomeric separation of unmodified amino acids, amino acid amides...


    pub_type: 杂志文章


    authors: Galaverna G,Corradini R,Dossena A,Marchelli R,Dallavalle F

    更新日期:1996-01-01 00:00:00

  • Conformational spaces of Cinchona alkaloids.

    abstract::A systematic and comprehensive study of the conformational spaces of the Cinchona alkaloids quinine, quinidine, cinchonine, cinchonidine, epiquinine, epiquinidine, epicinchonine, and epicinchonidine using the semiempirical PM3 method is described. The results were analyzed in terms of syn/anti and open/closed/hindered...


    pub_type: 杂志文章


    authors: Caner H,Biedermann PU,Agranat I

    更新日期:2003-08-01 00:00:00

  • The so-called "interconversion" of stereoisomeric drugs: an attempt at clarification.

    abstract::A variety of reactions can be categorized under the global concept of the "interconversion of stereoisomers." Thus, racemization or epimerization can result from inversion of labile chiral centers. From the examples available, some predictive rules are suggested for a chiral center of the type R"R'RC-H undergoing base...


    pub_type: 杂志文章,评审


    authors: Testa B,Carrupt PA,Gal J

    更新日期:1993-01-01 00:00:00

  • Organocatalytic aza-Michael/retro-aza-Michael reaction: pronounced chirality amplification in aza-Michael reaction and racemization via retro-aza-Michael reaction.

    abstract::A detailed experimental investigation of an aza-Michael reaction of aniline and chalcone is presented. A series of Cinchona alkaloid-derived organocatalysts with different functional groups were prepared and used in the aza-Michael and retro-aza-Michael reaction. There was an interesting finding that a complete revers...


    pub_type: 杂志文章


    authors: Cai YF,Li L,Luo MX,Yang KF,Lai GQ,Jiang JX,Xu LW

    更新日期:2011-05-01 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...


    pub_type: 杂志文章


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

    更新日期:2010-02-01 00:00:00

  • Chiral recognition ability and solvent versatility of bonded amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase: enantioselective liquid chromatographic resolution of racemic N-alkylated barbiturates and thalidomide analogs.

    abstract::The chiral recognition ability and solvent versatility of a new chiral stationary phase containing amylose 3,5-dimethylphenylcarabamate immobilized onto silica gel (CHIRALPAK IA) is investigated. Thus, the direct enantioselective separation of a set of racemic N-alkylated barbiturates and 3-alkylated analogs of thalid...


    pub_type: 杂志文章


    authors: Ghanem A,Al-Humaidi E

    更新日期:2007-06-01 00:00:00

  • A new water soluble Zn-salophen derivative as a receptor for alpha-aminoacids: unexpected chiral discrimination.

    abstract::A new water soluble zinc-salophen complex with appended D-glucose moieties was synthesized and characterized. Its binding properties toward six aminoacids were investigated by UV-vis spectrophotometric titrations. Association constants showed to be unfavorably affected by increasing steric hindrance of the side chain....


    pub_type: 杂志文章


    authors: Dalla Cort A,De Bernardin P,Schiaffino L

    更新日期:2009-01-01 00:00:00

  • N,N-dimethylcarbamyl derivatives of oxazepam.

    abstract::Three N,N-dimethylcarbamyl derivatives of oxazepam (1-(N,N-dimethylcarbamyl)oxazepam, 3-O-(N,N-dimethylcarbamyl)oxazepam, and 1,3-O-bis(N,N-dimethylcarbamyl) oxazepam) and a 3-O-acyl-1-(N,N-dimethylcarbamyl)-oxazepam were synthesized from either oxazepam or demoxepam. Enantiomeric pairs of these derivatives and of cam...


    pub_type: 杂志文章


    authors: Yang SK,Lu XL

    更新日期:1991-01-01 00:00:00