Chiral analysis in food science

Álvarez-Rivera, Gerardo; Bueno, Mónica; Ballesteros-Vivas, Diego; Cifuentes, Alejandro

doi:10.1016/j.trac.2019.115761

Cited by 74 publications

(40 citation statements)

References 91 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Separation of enantiomers is undoubtedly a matter of crucial importance in diverse research areas [44], allowing to achieve different goals, such as preparative enantioresolution of chiral drugs and other analytes [177,178], monitoring enantiomeric reactions [167,179], evaluation of enantiomeric purity in quality control [180,181], food analysis [182,183], stereochemistry determination of natural compounds [184,185], pharmacokinetic [25] and environmental studies [186,187], among other applications.…”

Section: Enantioresolution Studies By Chromatographic and Electrophoretic Methods Using Hsa As Chiral Selectormentioning

confidence: 99%

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

et al. 2021

View full text Add to dashboard Cite

The interaction between proteins and drugs or other bioactive compounds has been widely explored over the past years. Several methods for analysis of this phenomenon have been developed and improved. Nowadays, increasing attention is paid to innovative methods, such as high performance affinity liquid chromatography (HPALC) and affinity capillary electrophoresis (ACE), taking into account various advantages. Moreover, the development of separation methods for the analysis and resolution of chiral drugs has been an area of ongoing interest in analytical and medicinal chemistry research. In addition to bioaffinity binding studies, both HPALC and ACE al-low one to perform other type of analyses, namely, displacement studies and enantioseparation of racemic or enantiomeric mixtures. Actually, proteins used as chiral selectors in chromatographic and electrophoretic methods have unique enantioselective properties demonstrating suitability for the enantioseparation of a large variety of chiral drugs or other bioactive compounds. This review is mainly focused in chromatographic and electrophoretic methods using human serum albumin (HSA), the most abundant plasma protein, as chiral selector for binding affinity analysis and enantioresolution of drugs. For both analytical purposes, updated examples are presented to highlight recent applications and current trends.

show abstract

Section: Enantioresolution Studies By Chromatographic and Electrophoretic Methods Using Hsa As Chiral Selectormentioning

confidence: 99%

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Enantiomeric resolution is of central importance in many fields including pharmaceutical, pharmacological, clinical, food, agrochemical, environmental, biomedical and forensic analysis. Stereospecific analyte monitoring is widely accomplished via use of chromatographic methods which require rather expensive chiral stationary phases [1][2][3][4][5][6][7][8][9] and capillary electromigration methods which provide high resolution at low cost [10][11][12][13][14][15][16][17][18][19][20]. For enantiomeric separation under electrokinetic conditions, a chiral selector or a mixture of selectors, together with proper buffer conditions, provide the basis for the anticipated separation of stereoisomers.…”

Section: Introductionmentioning

confidence: 99%

Bioanalysis of drugs and their metabolites by chiral electromigration techniques (2010–2020)

Caslavska

Thormann

2021

Electrophoresis

View full text Add to dashboard Cite

The further development and application of capillary electromigration techniques for the enantioselective determination of drugs and their metabolites in body fluids, tissues, and in vitro preparations during the 2010 to 2020 time period continued to proof their usefulness and attractiveness in bioanalysis. This review discusses the principles and important aspects of capillary electrophoresis‐ based chiral drug bioassays, provides a survey of the assays reported during the past 10 years and presents an overview of the key achievements encountered in that time period. For systems with charged chiral selectors, special attention is paid on assays that feature field‐amplified sample injection to enable the determination of ppb levels of analytes and optimized online incubation procedures for the rapid assessment of a metabolic pathway. Applications discussed encompass the pharmacokinetics of drug enantiomers in vivo and in vitro, the impact of inhibitors on metabolic steps, the elucidation of the stereoselectivity of drug metabolism in vivo and in vitro, and drug enantiomers in toxicological, forensic, and doping analysis.

show abstract

“…For many years, chiral separations have been realized by many chromatographic methods including liquid, supercritical fluid chromatography, and GC as well as CE [4–8]. A glimpse at the literature in the last few decades reveals the fact that a plethora of literature emerged focusing on the direct chiral separation techniques where no chemical derivatization is required [9–16]. The extensive research in this area, especially in HPLC, has culminated in the development and commercialization of several chiral stationary phases (CPSs) based on various chiral selectors such as cyclodextrins (CDs), cyclic antibiotics, and polysaccharides such as cellulose and amylose carbamates and recently cyclofructans [17–23].…”

Section: Introductionmentioning

confidence: 99%

Capillary electrophoresis and molecular modeling of the chiral separation of aromatic amino acids using α/β‐cyclodextrin and 18‐crown‐6

et al. 2021

View full text Add to dashboard Cite

In this work, chiral separation of enantiomers of three amino acids was achieved using capillary electrophoresis technique with α‐cyclodextrin (αCD) as a running buffer additive. Only tryptophan has exhibited baseline separation in the presence of αCD, while the enantiomers of the other two amino acids, phenylalanine and tyrosine, were only partially separated. The addition of 18‐crown‐6 (18C6) as a second additive imparted only slight improvement to the separation of all enantiomers. On the other hand, all three racemic amino acid mixtures demonstrated no indication of separation when the larger cavity cyclodextrin members, β‐ and γCD, are used as running buffer chiral additives. However, remarkable improvements in the separation of the enantiomers of phenylalanine and tyrosine were obtained when 18C6 is used together with βCD as a running buffer additive. Surprisingly, tryptophan enantiomers were not separated by the dual additive system of cyclodextrin and crown ether. Using electrospray ionization mass spectrometry (ESI‐MS), all amino acids were found to form stable binary complexes with individual hosts as well as ternary compounds involving the crown ether and the cyclodextrin. Furthermore, we used molecular dynamics (MD) simulations to build a clear picture about the interaction between the guest and the hosts. Most of these complexes remained stable throughout the simulation times, and the molecular dynamics study allowed better understanding of these supramolecular assemblies.

show abstract

Chiral analysis in food science

Cited by 74 publications

References 91 publications

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

Enantioresolution and Binding Affinity Studies on Human Serum Albumin: Recent Applications and Trends

Bioanalysis of drugs and their metabolites by chiral electromigration techniques (2010–2020)

Capillary electrophoresis and molecular modeling of the chiral separation of aromatic amino acids using α/β‐cyclodextrin and 18‐crown‐6

Contact Info

Product

Resources

About