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PubMedDate not supplied

Electrokinetic separation of enantiomers using a capillary coated with poly-terguride.

Enantioseparation of 2-arylpropionic acids (Flobufen) and dansyl-derivatives of amino acids can be achieved in 10-15 min by electrochromatography using a capillary coated with poly-terguride. It was found that the analytes, in the range of the buffer pH between 2.5-4.0, were driven by anodic electroosmotic flow originated by the positively charged moieties of the ergolinic skeleton, and, only partially, by their anodic electrophoretic mobility. The enantiomers eluted with the same sequence, e.g. L- or (S)-isomer more retained than D- or (R)-, which was observed in HPLC separations on terguride-silica based CSPs, thus indicating that racemates were resolved by a similar chiral recognition mechanism. The retention of the solutes was affected by the concentration and composition of the effluent. An other mobile phase variable, strongly affecting the selectivity, was the pH of the buffer.

Amino Acids↗
PubMed1997

Determination of protein binding of troglitazone stereoisomers by fluorometric titration.

Determination of the protein binding of troglitazone is difficult because of its high adsorption to filters and membranes and the instability of the stereoisomers. We attempted to assess the protein binding of four stereoisomers of troglitazone in the plasma and albumin from several species by the method using fluorescent probes. The inhibition constants (Ki) for the stereoisomers of troglitazone were obtained from the decreases in fluorescence intensity of dansylsarcosine caused by competitive inhibition. Each stereoisomer of troglitazone displaced dansylsarcosine, a typical specific fluorescent probe for the diazepam binding site on human serum albumin (HSA). The highest binding affinity for dansylsarcosine was observed with HSA (dissociation constant, Kd,1 = 0.5 microM), while it was lowest in the mouse (Kd,1 = 18 microM). The Ki values for KK and ddY mouse plasma and mouse and rat albumin were in the range 2-15 microM, and there were no large variations among stereoisomers, the maximum differences being twofold. For human plasma and albumin, the displacement could not be accounted for by a simple competitive inhibition. Comparison between unbound fraction (fu) values calculated from thus obtained Ki values and those of a mixture of the four stereoisomers determined by high-performance frontal analysis showed that the fu values obtained by fluorometric titration were higher, while the relative differences among the stereoisomers in terms of animal species and strain were comparable for the two methods. Small differences in protein binding among stereoisomers of troglitazone may not be the major reason for their stereoselective pharmacokinetics.

Animals↗
PubMed1996

Albumin binding sites for etodolac enantiomers.

Non-steroidal anti-inflammatory drugs (NSAIDs) are strongly bound to human serum albumin (HSA), mainly to sites I and II. The aim of this study was to characterize the binding site(s) of etodolac enantiomers under physiological conditions (580 microM HSA) using equilibrium dialysis. The protein binding of etodolac enantiomers, alone or in various ratios, was studied in order to evaluate the potential competition between them. Our results showed that (S)-etodolac was more strongly bound to HSA than (R)-etodolac. The displacement of one enantiomer by its antipode was observed only at high concentrations of the competitor, and was more pronounced for (S)-form. Displacement studies of the enantiomers by specific probes of sites I and II of albumin, dansylamide, and dansylsarcosine, respectively, showed that (R)-etodolac was slightly displaced by both these probes whereas the free concentration of (S)-etodolac increased markedly in the presence of dansylsarcosine. Moreover, the binding of ligands to sites I and II is usually affected by alkaline pH, by chloride ions, and by fatty acids. For etodolac, the presence of 0.1 and 1 M chloride ions and increasing pH (5.5-9) decreased the binding of both enantiomers. The same result was obtained with addition of octanoic acid. Conversely, the addition of oleic, palmitic, or stearic acid to the protein solution increased the binding of (R)-etodolac, but decreased that of its antipode. All these findings suggest (R)- and (S)-etodolac interact mainly with site II of HSA, and that the (R)-isomer is also bound to site I under physiological conditions.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed1999

Evaluation of the macrocyclic antibiotic LY333328 as a chiral selector when used as a mobile phase additive in narrow bore HPLC.

The macrocyclic antibiotic LY333328 has been evaluated as a chiral selector for the enantioseparation of nine dansylated amino acids. This macrocyclic glycopeptide was used as a chiral mobile phase additive (CMPA) in conjunction with narrow bore high-performance liquid chromatography (HPLC). The key mobile phase parameters of LY333328 concentration and buffer pH were varied, along with variations in stationary phases consisting of C8, phenyl, cyano, and silica. After observing and plotting changes in retention and resolution based on corresponding variation in these parameters, a better understanding of the behavior of this chiral selector was obtained. The pKa values of the dansyl amino acid analytes and LY333328 were measured and used to gain a better understanding of the microenvironment in which these enantioseparations occur. Optimized conditions resulted in the baseline separation of eight of nine dansyl amino acids.

Amino Acids↗
PubMed2000

Changes in biogenic amines in mature and germinating legume seeds and their behavior during cooking.

Ungerminated legume seeds (broad bean, chick pea and lupine) were contained all tested biogenic amines. Tryptamine (TRY) was the main biogenic amine detected, and its concentration considerably increased during the germination. beta-Phenylethylamine (PHE) was detected in small amounts and its concentration slowly increased during germination. The concentration of tyramine (TYR) showed a fluctuation pattern of changes during germination in all tested legumes. The concentrations of cadaverine (CAD) and putrescine (PUT) increased during the germination period in all tested grains. However, histamine (HIS) showed a fluctuated pattern of changes in both broad bean and lupine, and a gradual increase in chick pea. Spermidine (SPD) and spermine (SPM) contents of broad bean and chick pea showed a fluctuation pattern of change, while, a decrement trend of change was recorded for lupine along the germination period. By cooking, legume samples became free of biogenic amines which appeared in the boiling water. Heat treatment seems to have little effect on the concentration of biogenic amines in legume sprouts. The amounts of biogenic amines detected in the boiling water are less than the initial amounts of the sprouts (expected amounts).

Biogenic Amines↗
PubMed1999

Determination of aminoglutethimide enantiomers as dansyl derivative in human plasma by HPLC with fluorescence detection.

Determination of aminoglutethimide enantiomers as a dansyl derivative in plasma by HPLC has been achieved using cellulose tris(3,5-dimethylphenyl carbamate) chiral stationary phase known as Chiralcel OD, and a mobile phase consisted of ethanol-cyclohexane-methanol (95:5:2 v/v/v). The limit of detection for each enantiomer of aminoglutethimide using fluorescence detector was 20 ng ml-1.

Aminoglutethimide↗
PubMed1999

Enantiometric separation of amino acids by copper (II)-L-arginine ligand exchange capillary zone electrophoresis.

A novel method for the separation of amino acid enantiomers by ligand exchange capillary zone electrophoresis (CZE) using a chiral Cu(II)-L-arginine ligand was developed in this paper. The effects of the buffer concentration, pH, the molar ratio of L-arginine to Cu(II), and the total concentrations of Cu(II) and L-arginine on the migration times and resolutions of chiral amino acids were investigated. The optimum experimental conditions were 40 mmol/L of NH4OAc, pH 7.0, the 2:1 concentration ratio of L-arginine to Cu(II), 1 mmol/L CuSO4 x 5H2O and 2 mmol/L L-arginine. Using the proposed method, six different dansyl-amino acids were separated successfully with the resolution ranging from 1.1 to 2.3 in less than 15 min.

Amino Acids↗
PubMed1999

Enantiomeric separations of dansyl amino acids using the macrocyclic antibiotic A35512B as a chiral selector in capillary electrophoresis.

The macrocyclic antibiotic A35512B was examined as a chiral selector for capillary electrophoresis (CE) using thirteen racemic dansyl amino acids as test analytes. The chiral selectivity of A35512B was evaluated as a function of the run buffer pH, antibiotic concentration, and organic modifier composition. After optimizing these parameters, the macrocylic antibiotic A35512B provided high resolutions of all the enantiomers for the thirteen dansyl amino acids tested in this study.

Amino Acids↗
PubMed1999

Chiral separation of dansyl-DL-amino acids with micellar systems containing copper (II) ion and N-n-dodecyl-L-proline in electrokinetic capillary chromatography.

Enantiomers of dansylated DL-amino acids were resolved by chiral copper (II)-N-n-dodecyl-L-proline (1) complexes incorporated in micelles of sodium dodecyl sulfate (SDS) in electrokinetic capillary chromatography (EKC). This resolution is caused by formation of diastereomeric ternary complexes consisting of chiral ligand 1, central copper (II) ion and enantiomeric amino acid derivatives in micellar phase. However, the resolution was not observed when SDS with an anionic polar head grop was replaced with dodecyl trimethylammonium brode (DTMAB) with a cationic polar head group. The ratio between copper (II) ion and 1 in the complex in either SDS or DTMAB was measured by UV-visible spectra, which respond to the d-d transition of copper (II). Mechanism of separation should be discussed in terms of effect of surfactant structures on constitution of copper (II) ion and 1 in the micellar phase and that of arene substituent structures linked to sulfonamide units in amino acid derivatives to be separated.

Amino Acids↗
PubMed2000

Preparative-scale isoelectric focusing separation of enantiomers using a multicompartment electrolyzer with isoelectric membranes.

The IsoPrime multicompartment electrolyzer, equipped with a series of isoelectric membranes with closely spaced pI values, was used for the first time for the preparative-scale separation of the enantiomers of dansyl phenylalanine with hydroxypropyl beta-cyclodextrin as resolving agent. The final separation conditions could be established easily in three successive experiments by rationally narrowing the pH steps between the neighboring isoelectric membranes. The final separation yielded products with an enantiomeric excess greater than 99.9%, at production rates of about 0.1 mg/h. The greatest experimental difficulty was caused by the relatively high salt content of the hydroxypropyl beta-cyclodextrin used, which resulted in high conductivity and limited the maximum field strength one could use.

Cyclohexylamines↗
PubMed2000

Chiral discrimination of N-carbazole-carbonyl derivatives of alpha-amino acids with a short linear alkyl side chain by bovine serum albumin.

Chiral discrimination of racemic carbazole carbonyl (CC)-amino acids with linear alkyl sidechain (C(1)-C(4)) by bovine serum albumin (BSA) was investigated by competitive replacement experiments using dansyl-L-proline and dansyl-D-norvaline as fluorescent probes. It was found that the CC derivatives of the D-forms of alanine (C(1)), amino butyric acid (C(2)), norvaline (C(3)), and norleucine (C(4)) bound to the dansyl-L-proline site much more strongly than their L-forms, whereas the interactions between both enantiomers of these amino acids with dansyl-D-norvaline site were slight.

Alanine↗
PubMed2000

Cyclodextrin dimers as receptor molecules for steroid sensors.

The dansyl-modified dimer 9 complexes strongly with the steroidal bile salts. Relative to native beta-cyclodextrin, the binding of cholate (1a) and deoxycholate (1b) salts is especially enhanced. These steroids bind exclusively in a 1:1 fashion. For other bile salts (1c-1e) both 1:1 and 1:2 complexes were observed with stabilities similar to those of native beta-cyclodextrin. This indicates that only one cavity is used, with a small contribution from the second. The difference is attributed to the absence of a 12-hydroxy group in the second group of steroids. Comparison with a dimer that lacks the dansyl moiety (6) shows that this group especially hinders the cooperative binding of la and 1b. The smaller interference in the binding of the other steroids indicates that self-inclusion of the dansyl moiety hardly occurs. This weak self-inclusion is supported by fluorescence studies. The dansyl fluorescence of dimer 9 is less blue-shifted than that of other known dansyl-appended cyclodextrin derivatives; this is indicative of a more polar micro-environment. Addition of guests causes a change in fluorescence intensity.

Bile Acids and Salts↗
PubMed2000

Fluorescence imaging of frit effects in capillary separations.

The gradient of five dansylated amino acids in a capillary-based separation system commonly used in capillary liquid chromatography (LC) or capillary electrochromatography (CEC) was followed and examined in detail using a detection method based on laser-induced fluorescence imaging. The detection system consisted of an XeCl excimer laser and an image-intensified charge-coupled device (CCD) camera. Fluorescence intensity profiles along the capillary column were displayed and continuously updated on a computer screen. The detector system enabled the separation dynamics in the column to be monitored. The experiments were focused on the course of events, especially at interfaces. The processes occurring at the beginning of the reversed-phase packing material were studied as well as at the transition from stationary phase to the outlet frit and the open tubular area. Striking differences in signal intensity and separation efficiency were revealed depending on where on the column detection was performed. Furthermore, adsorption of the analytes on the frits was observed.

Amino Acids↗
PubMed2000

Enantiomeric separation by capillary electrochromatography. I. Chiral separation of dansyl amino acids and organochlorine pesticides on a diol-silica dynamically coated with hydroxypropyl-beta-cyclodextrin.

In this work, a commercially available diol-silica stationary phase was converted in situ to a chiral stationary phase by dynamically coating it with hydroxypropyl-beta-cyclodextrin (HP-beta-CD). This stationary phase was shown useful for the capillary electrochromatography (CEC) separation of neutral and anionic enantiomers such as some organochlorine pesticides and dansyl amino acids, respectively. The inclusion of HP-beta-CD in the mobile phase to produce the in situ chiral stationary phase allowed the rapid separation of the anionic dansyl amino acid enantiomers at relatively low electroosmotic flow (EOF). The formation of host-guest complexes between the dansyl amino acids and the neutral HP-beta-CD in the mobile phase lowered the actual charge-to-mass ratios of the anionic solutes, thus speeding up their transport by the EOF across the packed capillary column. Several parameters affecting enantioseparation were investigated, including the concentration of HP-beta-CD, ionic strength, pH, and organic modifier content of the mobile phase.

2-Hydroxypropyl-beta-cyclodextrin↗
PubMed2000

Enantiomeric separation by capillary electrochromatography. II. Chiral separation of dansyl amino acids and phenoxy acid herbicides on sulfonated silica having surface-bound hydroxypropyl-beta-cyclodextrin.

A chiral silica-based stationary phase having surface-bound hydroxypropyl-beta-cyclodextrin (HP-beta-CD) with a relatively strong electroosmotic flow (EOF) was introduced for enantioseparation by capillary electrochromatography (CEC). The stationary phase contained a hydrophilic sulfonated sublayer to which a chiral top layer of HP-beta-CD was immobilized. While the sulfonated sublayer was to provide a relatively strong EOF, the top HP-beta-CD was to confer the desired chiral recognition towards enantiomeric solutes. This HP-beta-CD sulfonated silica (CDSS) stationary phase proved useful for the rapid separation of anionic enantiomers such as dansyl amino acids and phenoxy acid herbicides. The effects of the organic modifier content, pH, and ionic strength of the mobile phase on enantioseparation were investigated. Under the optimized separation conditions, ten dansyl amino acids and six phenoxy acid herbicides were enantioseparated with a resolution greater than unity.

2-Hydroxypropyl-beta-cyclodextrin↗
PubMed2001

Enantiomer separation by nonaqueous and aqueous capillary electrochromatography on cyclodextrin stationary phases.

Native beta- and gamma-cyclodextrin bound to silica (ChiraDex-beta and ChiraDex-gamma) were packed into capillaries and used for enantiomer separation by capillary electrochromatography (CEC) under aqueous and nonaqueous conditions. Negatively charged analytes (dansyl-amino acids) were resolved into their enantiomers by nonaqueous CEC (NA-CEC). The addition of a small amount of water to the nonaqueous mobile phase enhanced the enantioselectivity but increased the elution time. The choice of the background electrolyte (BGE) determined the direction of the electroosmotic flow (EOF). With 2-(N-morpholino) ethanesulfonic acid (MES) or triethylammonium acetate (TEAA) as BGE an inverse EOF (anodic EOF) was observed while with phosphate a cathodic EOF was found. The apparent pH (pH*), the concentration of the BGE, and the nature of the mobile phase strongly influenced the elution time, the theoretical plate number and the chiral separation factor of racemic analytes.

Acetonitriles↗
PubMed2001

Chemically L-prolinamide-modified monolithic silica column for enantiomeric separation of dansyl amino acids and hydroxy acids by capillary electrochromatography and mu-high performance liquid chromatography.

A silica-based chiral monolithic column prepared by sol-gel process and chemical modification of chiral selector was used for enantioseparation of dansyl amino acids and hydroxy acids by capillary electrochromatography (CEC) and mu-high-performance liquid chromatography (mu-HPLC). L-Prolinamide was modified as a chiral selector. The chiral stationary phase (CSP), the chiral complex of Cu(II) with L-prolinamide, provides an anodic electroosmotic flow (EOF) in CEC. The EOF was found to be dependent on applied electric field strength, the pH, and the composition of mobile phases. Scanning electron micrograph showed that monolithic columns have the morphology of continuous skeleton and large through-pore. D-Enantiomers migrated before L-enantiomers except for dansyl-(Dns)-DL-Ser. The separation efficiencies of up to 17600 (D) and 13,200 plates m(-1) (L) were achieved for the separation of DL-indole-3-lactic acid.

Acetonitriles↗
PubMed1977

Transport and hydrolysis of peptides by microorganisms.

The structural specificities of the dipeptide and oligopeptide permeases of E. coli are briefly reviewed and related to the requirements found for other microorganisms. New, quick, sensitive methods for studying peptide transport are described, based on the following: (i) peptide-dependent incorporation of free radioactive amino acid into newly synthesized protein by a double amino acid auxotroph, (ii) colorimetric assay of peptide-dependent enzyme synthesis by an amino acid auxotroph, (iii) dansyl fingerprint technique. These approaches provide information on peptide binding affinity to a permease and rates of peptide uptake and amino acid efflux. Among current and future research areas considered are: the influence of the pKb of the N-terminal amino group on transport, generality of peptide transport in microorganisms, energy coupling and regulation, involvement of binding proteins, and the 'smugglin' concept. Peptide hydrolysis, and nutritional ultilization of peptides, by microorganisms are briefly discussed.

Bacteria↗