Chiral selectivity of guanosine media in capillary electrophoresis

Dong, Yingying; McGown, Linda B.

doi:10.1002/elps.201100007

Cited by 16 publications

(30 citation statements)

References 23 publications

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“…The peaks were red-shifted relative to the single-component FY gel, indicating a different environment in the multicomponent system, potentially bundling with the Ag-GMP filaments. For example, tyrosine has previously been reported to intercalate between GMP stacks [ 46 , 47 ]. Thus, it is possible that the hybrid hydrogels consist of heterogeneous filaments.…”

Section: Resultsmentioning

confidence: 99%

Stimuli-Responsive Nucleotide–Amino Acid Hybrid Supramolecular Hydrogels

Mulvee

Vasiljević

Mann

et al. 2021

Gels

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The ability to assemble chemically different gelator molecules into complex supramolecular hydrogels provides excellent opportunities to construct functional soft materials. Herein, we demonstrate the formation of hybrid nucleotide–amino acid supramolecular hydrogels. These are generated by the silver ion (Ag+)-triggered formation of silver–guanosine monophosphate (GMP) dimers, which undergo self-assembly through non-covalent interactions to produce nanofilaments. This process results in a concomitant pH reduction due to the abstraction of a proton from the guanine residue, which triggers the in situ gelation of a pH-sensitive amino acid, N-fluorenylmethyloxycarbonyl tyrosine (FY), to form nucleotide–amino acid hybrid hydrogels. Alterations in the supramolecular structures due to changes in the assembly process are observed, with the molar ratio of Ag:GMP:FY affecting the assembly kinetics, and the resulting supramolecular organisation and mechanical properties of the hydrogels. Higher Ag:GMP stoichiometries result in almost instantaneous gelation with non-orthogonal assembly of the gelators, while at lower molar ratios, orthogonal assembly is observed. Significantly, by increasing the pH as an external stimulus, nanofilaments comprising FY can be selectively disassembled from the hybrid hydrogels. Our results demonstrate a simple approach for the construction of multicomponent stimuli-responsive supramolecular hydrogels with adaptable network and mechanical properties.

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Section: Resultsmentioning

confidence: 99%

Stimuli-Responsive Nucleotide–Amino Acid Hybrid Supramolecular Hydrogels

Mulvee

Vasiljević

Mann

et al. 2021

Gels

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“…Dong and McGown [72] studied so-called G-gels, formed by self-association of monomeric guanosine for the CE enantioseparations. Guanosine forms gels composed of so-called G-tetrads (G-quartets) which are formed through hydrogen bonding between four guanosine molecules.…”

Section: New Chiral Selectors and Mechanistic Modelsmentioning

confidence: 99%

Chiral electromigration techniques in pharmaceutical and biomedical analysis

Scriba

2011

Bioanal Rev

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Capillary electromigration techniques are often considered ideal methods for enantioseparations due to their high separation selectivity and flexibility. Thus, numerous methods employing a chiral selector as pseudostationary phase in a background electrolyte have been developed and applied for the chiral analysis of drugs in bulk ware, pharmaceutical formulations and biological matrices. Furthermore, electromigration techniques have been combined with spectroscopic methods such as nuclear magnetic resonance in order to understand the complexation of analytes by chiral selectors. The present review focuses on recent developments and applications of chiral electromigration techniques in pharmaceutical and biomedical analysis including examples illustrating analyte-selector complex formation or mechanistic studies which have been published between January 2009 and July 2011. Selector-mediated chiral separations clearly dominate while no applications of capillary electrochromatography to pharmaceutical or biomedical analysis have been reported during this period of time.

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“…Improvement of gels formed by self‐association of monomeric guanosine was tested for d / l Trp separation. The hydrogen‐bonded tetrads formed by guanosine nucleotides stacked the monomer in columnar, helical aggregates (stabilized by π–π interactions) with centrally located cations . Resolutions around 1 were reached while, for example, d / l Phe and d / l Tyr enantiomers were not resolved.…”

Section: Enantioselective Separationsmentioning

confidence: 99%

Recent advances in amino acid analysis by capillary electromigration methods, 2011–2013

et al. 2013

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This article describes the most important research published on amino acid (AA) analysis using CE during the period from June 2011 to May 2013, and follows the format of the previous articles of Smith (Electrophoresis 1999, 20, 3078-3083), Prata et al. (Electrophoresis 2001, 22, 4129-4138), and Poinsot et al. (Electrophoresis 2003, 24, 4047-4062; Electrophoresis 2006, 27, 176-194; Electrophoresis 2008, 29, 207-223; Electrophoresis 2010, 31, 105-121; Electrophoresis 2012, 33, 14-35). We present new developments in AA analysis with CE, mainly describing the use of MS or LEDs for detection following conventional or enantiomeric separation developments. In addition, in an application part, we describe neurochemical or clinical studies, metabolomics for plant extracts and biological fluids, and finally works focused on AAs in food and agricultural applications.

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Chiral selectivity of guanosine media in capillary electrophoresis

Cited by 16 publications

References 23 publications

Stimuli-Responsive Nucleotide–Amino Acid Hybrid Supramolecular Hydrogels

Stimuli-Responsive Nucleotide–Amino Acid Hybrid Supramolecular Hydrogels

Chiral electromigration techniques in pharmaceutical and biomedical analysis

Recent advances in amino acid analysis by capillary electromigration methods, 2011–2013

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