enantiomer separation

(S)-Lifitegrast (LFT) is the novel integrin antagonist, approved by the Food and drug administration, to treat signs and symptoms of dry eye disease. Synthesis of racemic LFT, preparative and analytical enantiomer separation, and chiral interconversion studies are lacking in the literature. Hence, in our study, synthesis of LFT racemate, chiral preparative purification procedure of enantiomer, and comprehensive analytical advancements are focused on rapid enantioselective separation and pH-dependent chiral interconversion studies...

Glutamine is the most abundant free proteinogenic α-amino acid. It is naturally produced in the organism and acts as a precursor for the synthesis of different biologically important molecules (such as proteins or nucleotides). However, under stressful conditions, the organism is unable to produce it in enough amounts to function properly. Thus, glutamine (Gln)-based supplements have become increasingly popular over the last decade. Since legal regulations establish that amino acid-based dietary supplements must contain only the L-enantiomer and not the racemate, adequate chiral methodologies are required to achieve their quality control...

Ibuprofen (IBP), the 29th most prescribed drug in the United States in 2019, is a widely used nonsteroidal anti-inflammatory drug (NSAID) comprising two enantiomers, (R)-IBP and (S)-IBP, collectively known as (RS)-IBP. This critical review examines analytical techniques for the enantioselective separation and determination of IBP enantiomers, crucial for pharmaceutical and clinical applications. The review focuses on state-of-the-art methods, including chromatographic techniques including high-performance liquid chromatography, gas chromatography, liquid chromatography-tandem mass spectrometry, and some other techniques...

The emergence of new synthetic cathinones continues to be a matter of public health concern. In fact, already known products (drugs) are being rapidly replaced by new structurally related alternatives, whereby modifications in the basic cathinone structure are used by manufacturers to circumvent the legislation. On the other hand, some derivatives of synthetic cathinones represent important pharmaceuticals with antidepressant properties. In the search for pharmaceutically relevant analogs, the main goal of the present study was to design and characterize novel cyclic α-tetralone-based derivatives of synthetic cathinones...

The different behavior of enantiomers of chiral compounds in non-isotropic environments (among them in living organism) is well known. On the other hand, the importance of a kinetic isotope effect in the biomedical field has become evident during past few decades. Thus, separation of both, enantiomers and isotopologues is now critical. Only very few published studies have attempted the simultaneous separation of enantioisotopologues. In this article we report baseline separation of partially deuterated isotopologues of a few amphetamine derivatives in high-performance liquid chromatography (HPLC) using achiral columns...

In this work, two different multiple dual-mode (MDM) counter-current chromatography methods, conventional MDM and modified MDM elution modes, were compared for the chiral separation of the ketoconazole enantiomers. The biphasic solvent system which consisted of n-hexane: isobutyl acetate: 0.1 mol/L phosphate buffer (2:4:6, v/v) (pH = 8.5) was employed as stationary phase and mobile phase. And the hydroxypropyl-β-cyclodextrin (HP-β-CD) with a concentration of 100 mmol/L was dissolved in the phosphate buffer, as the chiral selector...

Chirality plays a crucial role in different research fields, ranging from fundamental physico-chemistry to applied aspects in materials science and medicine. In this context, enantioselective loading and pumping of chiral analytes for analysis, separation, and cargo delivery applications is an interesting scientific challenge. Herein, we introduce artificial chiral soft electromechanical pumps based on a bi-layer film built up by electrodepositing polypyrrole and an inherently chiral conducting oligomer at its internal surface...

A chemical investigation of leaves of Viburnum chingii afforded eleven compounds, including one undescribed lignan ( 1 ), a pair of known phenylpropanoid enantiomers ( 2a / 2b ), and eight known lignans ( 3 - 10 ). Their structures were elucidated by detailed spectroscopic and comparative literature data analysis. The absolute configurations of compounds 1 was determined by comparing the experimental ECD data with the calculated values. The compounds 2a / 2b were separated successfully by a chiral chromatographic column...

Carbohydrates, in particular the d-enantiomers of ribose, 2-deoxyribose, and glucose, are essential to life's informational biopolymers (RNA/DNA) and for supplying energy to living cells through glycolysis. Considered to be potential biosignatures in the search of past or present life, our capacity to detect and quantify these essential sugars is crucial for future space missions to the Moon, Mars or Titan as well as for sample-return missions. However, the enantioselective analysis of carbohydrates is challenging and both research and routine applications, are lacking efficient methods that combine highly sensitive and reproducible detection with baseline enantioselective resolution and reliable enantiomeric excess (ee) measurements...

The first chiral methodology enabling the separation of indacaterol enantiomers was developed in this work by cyclodextrin-electrokinetic chromatography. Indacaterol (IND) is a chiral drug marketed as a pure enantiomer. Then, the separation and quantification of each enantiomer is of great importance for the quality control of pharmaceutical formulations. After selecting the most suitable chiral selector and background electrolyte, two Box-Behnken designs were achieved to optimize the electrophoretic conditions using two different approaches to shorten analysis times: i) decreasing the capillary length, or ii) performing a short-end injection...

BACKGROUND: With the rapid growth of the demand for optically pure compounds in the fields of biology, medicine and stereospecific synthesis, it is of great importance to develop efficient, economical, simple enantioseparation and analysis methods. Open tubular capillary electrochromatography (OT-CEC) has attracted much attention in the field of chiral separation, but its column capacity and the sensitivity of common-used optical detection are relatively low. Zeolite beta nanomaterial is both enantioselective and size-selective, providing suitable chiral microenvironment for chiral recognition, and amperometric detection (AD) avoids the low sensitivity caused by the short optical path in optical detection to some extent...

The sex pheromone of the azalea mealybug, Crisicoccus azaleae (Tinsley, 1898) (Hemiptera: Pseudococcidae), includes esters of a methyl-branched medium-chain fatty acid, ethyl and isopropyl (E)-7-methyl-4-nonenoate. These compounds are exceptional among mealybug pheromones, which are commonly monoterpenes. Determination of the absolute configuration is challenging, because both chromatographic and spectrometric separations of stereoisomers of fatty acids with a methyl group distant from the carboxyl group are difficult...

Two new depside derivatives 1 and 2 as well as a new pair of rosmarinic acid enantiomers 3a / b were isolated from the leaves of Perilla frutescens (L.) britt. The chemical structures of these compounds were identified based on detailed spectroscopic and physicochemical analyses (HR-ESI-MS, NMR) and comparison of literature data. Compounds 3a / b were obtained by chiral separation, and their absolute configurations were determined by comparison of experimental and calculated ECD spectra. Compounds 3a / b exhibited potential inhibitory activity on nitric oxide (NO) production induced by lipopolysaccharide in RAW264...

A series of six azaborahelicenes with varying electron-donor substitution at the 4-position of the aryl residue ( i.e. , naphthyl) or with variable π-extension of the aryl residue (thianthrenyl, anthryl, pyrenyl) was prepared with an efficient and flexible synthetic protocol. These different types of functionalization afforded notably pronounced intramolecular charge-transfer (ICT) character for the dyes with the strongest electron donor substitution (NMe2 ) or easiest to oxidize aryl residues, as evidenced by photophysical investigations...

Fast liquid chromatography (LC) amino acid enantiomer separation of 6-aminoquinolyl- N -hydroxysuccinimidyl carbamate (AQC) derivatives using a chiral core-shell particle tandem column with weak anion exchange and zwitterionic-type quinine carbamate selectors in less than 3 min was achieved. Enantiomers of all AQC-derivatized proteinogenic amino acids and some isomeric ones (24 in total plus achiral glycine) were baseline separated ( R s > 1.5 except for glutamic acid with R s = 1.3), while peaks of distinct amino acids and structural isomers (constitutional isomers and diastereomers of leucine and threonine) of the same configuration overlapped to various degrees...

In this study, we developed physically adsorbed multi-layer coatings using poly-l-lysine or poly(diallyldimethylammonium chloride) and gold nanoparticles, which were functionalized with bovine serum albumin for the chiral separation in electrochromatography. The approach involves sequentially depositing positively charged polymers and negatively charged citrate-stabilized gold nanoparticles. By repeating this modification cycle, we created two- and four-layer coatings, which were sequentially functionalized with albumin forming three- and five-layer coatings that were finally applied for the separation of enantiomers of dl-tryptophan...

The circularly polarized organic light-emitting diodes (CP-OLEDs) demonstrate promising application in 3D display due to the direct generation of circularly polarized electroluminescence (CPEL). But the chiral luminescence materials face challenges as intricated synthetic route and enantiomeric separation, etc. Herein, we design fresh CP-OLEDs based on chiral hole transport material instead of chiral emitters. A pair of hole transport enantiomers (R/S-NPACZ) exhibit intense dissymmetry factors (|gPL |) about 5...

This work presents a straightforward approach to the separation d/l-carnitine (d/l-Carn) using ion mobility-mass spectrometry (IM-MS) and theoretical calculations. Natamycin (Nat) was used as separation reagent to interact with the Carn, metal ions (G) were employed as ligand, the resultant ternary complexes [d/l-Carn + Nat + G]+ were observed experimentally. IM-MS results revealed that d/l-Carn could be baseline separated via complex formation using Li+ , Na+ , K+ , Rb+ , and Cs+ , with a maximum peak separation resolution (Rp-p ) of 2...

The development of new pharmaceutical compounds is challenging because most of them are based on enantiopure chiral molecules, which exhibit unique properties for therapy. However, the synthesis of pharmaceutical compounds in the absence of a chiral environment naturally leads to a racemic mixture. Thus, to control their synthesis, an asymmetric environment is required, and chiral homogeneous catalysts are typically used to synthesize enantiopure pharmaceutical compounds (EPC). Nevertheless, homogeneous catalysts are difficult to recover after the reaction, generating additional problems and costs in practical processes...

In this work, a capillary electrophoresis method was developed as a quality control tool to determine the enantiomeric purity of a series of five chiral compounds evaluated as potential severe acute respiratory syndrome coronavirus 2 3CL protease inhibitors. The first cyclodextrin tested, that is, highly sulfated-β-cyclodextrin, at 6% (m/v) in a 25 mM phosphate buffer, using a capillary dynamically coated with polyethylene oxide, at an applied voltage of 15 kV and a temperature of 25°C, was found to successfully separate the five derivatives...