Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

Fernandes, Carla; Teixeira, J. M.; Pinto, Madalena; Tiritan, Maria Elizabeth

doi:10.3390/molecules26185477

Cited by 12 publications

(6 citation statements)

References 95 publications

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“…Over the years, different synthetic approaches have been applied for preparation of CSPs, which embrace coating and immobilization methods. In addition to the classical and broadly applied coating and immobilization procedures, innovating strategies have been introduced [128]. The approaches applied for preparation of the homemade columns to perform the binding affinity studies shown in Table 4 were diverse, in which HSA was immobilized [111,112,123], adsorbed [113] or entrapped [125] on the chromatographic support.…”

Section: Zonal Analysismentioning

confidence: 99%

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

et al. 2021

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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.

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Section: Zonal Analysismentioning

confidence: 99%

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

et al. 2021

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“…Immobilization of CSPs, i.e., covalent chemical linkage of cellulose derivative-based CSs onto prefunctionalized silica gel, is thus the most obvious and suitable option to overcome the shortcomings of its "coated-only" counterparts, and their inherent problems with the dissolution of the CS in strong eluents, resulting column bleeding, and, in the worst case, destruction of the column material (Tang et al 2011;Padró and Keunchkarian 2018;Chankvetadze 2019;Fernandes et al 2021;Onishi et al 2022). One of the first immobilized, chemically robust CSPs were introduced by Okamoto et al as well, when they linked cellulose 3,5-dimethylphenyl carbamate-and 3,5-dichlorophenyl carbamate-type selectors onto 3-aminopropyl-functionalized silica gel by crosslinking with diisocyanates (Okamoto et al 1987).…”

Section: Introductionmentioning

confidence: 99%

Immobilization of a cellulose carbamate-type chiral selector onto silica gel by alkyne-azide click chemistry for the preparation of chiral stationary chromatography phases

Bui

Rosenau

2022

Cellulose

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A new synthesis strategy for the preparation of cellulose derivative-based chiral selectors and the subsequent mild immobilization onto pre-functionalized silica gel are introduced, utilizing Cu(I)-catalyzed alkyne-azide Huisgen cycloaddition (“click”) chemistry. A cellulose 3,5-dimethylphenyl carbamate derivative carrying propynyl carbamate groups was prepared by a combination of carbonate aminolysis and isocyanate chemistry. For immobilization, 3-azidopropyl-functionalized silica gel as an inert carrier was used, synthesized via a 3-chloropropyl intermediate. The chiral selector, as well as the inorganic/organic hybrid materials (silica gel/chiral selector), were comprehensively characterized by ATR-FTIR, solid-state 13C and 29Si NMR, liquid-state NMR, GPC, TGA, and elemental analysis. The enantioseparation performance of the immobilized-type chiral stationary phase was evaluated by HPLC with a set of representative chiral test analytes and different eluents and compared to a respective coated-type (=non-covalently bound) chiral stationary phase carrying the same selector quality and quantity on the same silica gel matrix. The immobilization did not adversely affect the chiral separation performance; on the contrary, in some chromatographic separations the immobilized-type chiral stationary phase surprisingly even surpassed the coated reference material. Graphical abstract

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“…The success of an efficient enantioseparation is mainly determined by the chiral discriminative power of the CSP. Over the years, various types of CSPs have been described [ 127 , 128 , 129 ]; nevertheless, the development of new CSPs for LC continued to be an evolutionary subject, encompassing the preparation of new chiral selectors [ 130 ], the introduction of new chromatographic supports [ 131 ], and the application of different synthetic approaches for the preparation of CSPs [ 132 ]. Macrocyclic antibiotic-based, crown ether-based, and ligand exchange-type ( Figure 4 ) are the most-used CSPs for the enantiomeric separation of amino acids and primary amine-containing compounds [ 133 , 134 , 135 , 136 ].…”

Section: Liquid Chromatography Methods For Determination Of Absolute ...mentioning

confidence: 99%

Absolute Stereochemistry Determination of Bioactive Marine-Derived Cyclopeptides by Liquid Chromatography Methods: An Update Review (2018–2022)

et al. 2023

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Cyclopeptides are considered as one of the most important classes of compounds derived from marine sources, due to their structural diversity and a myriad of their biological and pharmacological activities. Since marine-derived cyclopeptides consist of different amino acids, many of which are non-proteinogenic, they possess various stereogenic centers. In this respect, the structure elucidation of new molecular scaffolds obtained from natural sources, including marine-derived cyclopeptides, can become a very challenging task. The determination of the absolute configurations of the amino acid residues is accomplished, in most cases, by performing acidic hydrolysis, followed by analyses by liquid chromatography (LC). In a continuation with the authors’ previous publication, and to analyze the current trends, the present review covers recently published works (from January 2018 to November 2022) regarding new cyclopeptides from marine organisms, with a special focus on their biological/pharmacological activities and the absolute stereochemical assignment of the amino acid residues. Ninety-one unreported marine-derived cyclopeptides were identified during this period, most of which displayed anticancer or antimicrobial activities. Marfey’s method, which involves LC, was found to be the most frequently used for this purpose.

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Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

Cited by 12 publications

References 95 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

Immobilization of a cellulose carbamate-type chiral selector onto silica gel by alkyne-azide click chemistry for the preparation of chiral stationary chromatography phases

Absolute Stereochemistry Determination of Bioactive Marine-Derived Cyclopeptides by Liquid Chromatography Methods: An Update Review (2018–2022)

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