Triazole-linked Host Compounds for Chiral-Discrimination toward Amino Acid Ester Guests

Sato, Hirofumi; Shizuma, Motohiro

doi:10.5650/jos.57.503

Cited by 3 publications

(4 citation statements)

References 25 publications

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“…For instance, triazole-linked hosts have been used for chiral discrimination of enantiomeric alanine esters. 8 Cholic acid oligomers with 1,2,3-triazole groups have been used as chemosensors for the detection of trace amounts of metal ions.…”

Section: Letter Syn Lettmentioning

confidence: 99%

Synthesis of New 7,8-Dioxa[6]helicenes with Triazole Rings as Potential Molecular Tweezers

Kasabali¹,

Gündüz²,

Kaya³

et al. 2019

Synlett

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This study introduces new triazole-linked host compounds, which have been synthesized from 7,8-dioxa-bisnaphthalene and 7,8-dioxa[6]helicenes. These compounds have different cavities depending on being ‘v’-shaped or helicene structures. The dimeric structure of 7,8-dioxa-bisnaphthalene has also been obtained and crystal structure analysis confirmed that it contains an unusual seven-membered dihydrooxepine ring. All synthesized compounds can act as molecular tweezers for organic molecules and also metal ions.

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Section: Letter Syn Lettmentioning

confidence: 99%

Synthesis of New 7,8-Dioxa[6]helicenes with Triazole Rings as Potential Molecular Tweezers

Kasabali¹,

Gündüz²,

Kaya³

et al. 2019

Synlett

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“…Then, the chiral analyte (guest) reacts with the host molecules to form a diastereomeric mixture, which will simultaneously produce both labeled and unlabeled molecular ion peaks on the mass spectrum. 29 And an analysis was also performed to examine the ability of 7 chiral m-methyl-substituted polysaccharides to distinguish chiral alcohols. Fast atom bombardment (FAB), matrix-assisted laser desorption/ionization mass spectrometry, and electrospray ionization (ESI) can be used as soft ionization techniques.…”

Section: Host-guest (H-g) Associationmentioning

confidence: 99%

“…It was found that the oligosaccharides of the β-cello series had a high stereoselectivity to the S-tryptophan ammonium salt. 29 And an analysis was also performed to examine the ability of 7 chiral m-methyl-substituted polysaccharides to distinguish chiral alcohols. 30 Grigorean explored the interaction between 18-crown-6-tetracarboxylic acid and amino acids with enantiomer-labeled guest method to understand more deeply the enantiomeric recognition phenomena.…”

Section: Host-guest (H-g) Associationmentioning

confidence: 99%

Analysis of stereoisomers of chiral drug by mass spectrometry

2018

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Chiral molecules are of great importance in the life science since individual enantiomers may differ in biological activity, mechanism, and toxicity, making it necessary to explore efficient chiral analysis methods. Chromatography approaches are often used to differentiate enantiomers while mass spectrometry (MS) was thought to be blind in chiral analysis. With the development of MS technique, it began to play a more and more crucial part in chiral observation. In this review, we will give a detailed introduction of the analysis methods related to MS for chiral drugs, including its mechanism, applications, and future development.

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“…(Chart 5). Sato et al [83] synthesized the new triazole linked hosts, (193,194) (Figure 17) by versatile, rapid and high yield copper catalyzed Huisgen-1,3-dipolar cycloaddition (Click Chemistry) of linker azide with saccharide alkyne. These two compounds, 193, 194 then were investigated for the chiral recognition ability.…”

Section: Triazole Ring Containing Receptorsmentioning

confidence: 99%

Chiral Heterocycle-Based Receptors for Enantioselective Recognition

et al. 2018

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Abstract:The majority of biomolecules found in living beings are chiral, therefore chiral molecular recognition in living systems is crucial to life. Following Cram's seminal work on the crown-based chiral recognition, prominent research groups have reported innumerable chiral receptors with distinctly different geometrical features and asymmetry elements. Main applications of such chiral receptors are found in chiral chromatography, as for analytical purposes and for bulk separation of racemates.Incorporation of heterocyclic rings in these recognition systems added a new dimension to the existing group of receptors. Heterocycles have additional features such as availability of unshared electron pairs, pronounced conformational features, introduction of hydrogen bonding and presence of permanent dipoles as well as specific spectral properties in certain cases. These features are found to enhance binding properties of the receptors and the selectivity factors between opposite enantiomers, allowing them to be effectively separated. The review presents the synthetic approaches towards these heterocyclic receptors and their distinctly different behavior vis-à-vis carbocyclic receptors.

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Triazole-linked Host Compounds for Chiral-Discrimination toward Amino Acid Ester Guests

Cited by 3 publications

References 25 publications

Synthesis of New 7,8-Dioxa[6]helicenes with Triazole Rings as Potential Molecular Tweezers

Synthesis of New 7,8-Dioxa[6]helicenes with Triazole Rings as Potential Molecular Tweezers

Analysis of stereoisomers of chiral drug by mass spectrometry

Chiral Heterocycle-Based Receptors for Enantioselective Recognition

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