Inherently Chiral Azonia[6]helicene-Modified β-Cyclodextrin: Synthesis, Characterization, and Chirality Sensing of Underivatized Amino Acids in Water

Huang, Qinfei; Jiang, Li; Liang, Wenting; Gui, Jianchang; Xu, Dingguo; Wu, Wanhua; Nakai, Yoshito; Nishijima, Masaki; Fukuhara, Gaku; Mori, Tadashi; Inoue, Yoshihisa; Yang, Cheng

doi:10.1021/acs.joc.6b00130

Cited by 61 publications

(52 citation statements)

References 28 publications

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“…The chiral discrimination abilities were also found to be highly dependent on pH. A relatively high L/D selectivity of amino acids, up to 12.4, was observed as a consequence of the synergetic effects of the helicene auxiliary and β-cyclodextrin cavity [103].…”

Section: Helicene-based Chiral Recognition Via Self-assemblymentioning

confidence: 93%

“…Further, the chiral selectivity based on association constant evaluation indicates that the (M)-enantiomer of 191 interacts more strongly with DNA than the corresponding (P)-enantiomer of 191. [103]. The concept was to use water-insoluble 3-aza [6]helicene 194 in aqueous media in combination with the β-cyclodextrin asymmetry for the chiral recognition of amino acids in water.…”

Section: Helicene-based Chiral Recognition Involving Biologically Relmentioning

confidence: 99%

“…The overall studies demonstrated that the helicenes exhibit a noncovalent chiral recognition behavior via different functions, such as charge transfer complexation, crystallization, homocoupling reaction, layer structure formation, self-aggregation, [103]. The concept was to use water-insoluble 3-aza [6]helicene 194 in aqueous media in combination with the β-cyclodextrin asymmetry for the chiral recognition of amino acids in water.…”

Section: Helicene-based Chiral Recognition Via Self-assemblymentioning

confidence: 99%

“…The concept was to use water-insoluble 3-aza [6]helicene 194 in aqueous media in combination with the β-cyclodextrin asymmetry for the chiral recognition of amino acids in water. [103]. The concept was to use water-insoluble 3-aza [6]helicene 194 in aqueous media in combination with the β-cyclodextrin asymmetry for the chiral recognition of amino acids in water.…”

Section: Helicene-based Chiral Recognition Via Self-assemblymentioning

confidence: 99%

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Helicene-Based Chiral Auxiliaries and Chirogenesis

Hasan

Borovkov

2017

Symmetry

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Helicenes are unique helical chromophores possessing advanced and well-controlled spectral and chemical properties owing to their diverse functionalization and defined structures. Specific modification of these molecules by introducing aromatic rings of differing nature and different functional groups results in special chiroptical properties, making them effective chiral auxiliaries and supramolecular chirogenic hosts. This review aims to highlight these distinct structural features of helicenes; the different synthetic and supramolecular approaches responsible for their efficient chirality control; and their employment in the chirogenic systems, which are still not fully explored. It further covers the limitation, scope, and future prospects of helicene chromophores in chiral chemistry.

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Section: Helicene-based Chiral Recognition Via Self-assemblymentioning

confidence: 93%

Section: Helicene-based Chiral Recognition Involving Biologically Relmentioning

confidence: 99%

Section: Helicene-based Chiral Recognition Via Self-assemblymentioning

confidence: 99%

Section: Helicene-based Chiral Recognition Via Self-assemblymentioning

confidence: 99%

See 2 more Smart Citations

Helicene-Based Chiral Auxiliaries and Chirogenesis

Hasan

Borovkov

2017

Symmetry

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“…The CD and UV spectra were measured in a CH 2 Cl 2 solution of enantioenriched 8 derivatives (Figure 13c), which shows the CD signals of the mirror image, indicating that the compounds are of opposite bowl chirality. Recently, Yang and co-workers prepared azonia [6]helicene tethered with supramolecular host β-cyclodextrin, and used a chirality sensing probe for underivatized amino acids in water [89][90][91][92][93][94]. Indeed, tethered azonia [6]helicene acts as a conformationally robust chiral auxiliary to improve the chiral recognition ability of native cyclodextrins.…”

Section: Racemic (±)-21 Was Prepared By Aerobic Oxidation Of Racemic mentioning

confidence: 99%

Chiral Buckybowl Molecules

Kanagaraj

Lin

et al. 2017

Symmetry

Self Cite

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Buckybowls are polynuclear aromatic hydrocarbons that have a curved aromatic surface and are considered fragments of buckminsterfullerenes. The curved aromatic surface led to the loss of planar symmetry of the normal aromatic plane and may cause unique inherent chirality, so-called bowl chirality, which it is possible to thermally racemize through a bowl-to-bowl inversion process. In this short review, we summarize the studies concerning the special field of bowl chirality, focusing on recent practical aspects of attaining diastereo/enantioenriched chiral buckybowls through asymmetric synthesis, chiral optical resolution, selective chiral metal complexation, and chiral assembly formation.

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Alkyne‐Based Syntheses of Carbo‐ and Heterohelicenes

Gulevskaya

Tonkoglazova

2022

Adv Synth Catal

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[n]Helicenes are polycyclic aromatic molecules in which n ortho‐condensed benzene or other aromatic rings give rise to helical chiral and highly conjugated structures. The unique screw shape, helically extended π‐system and intriguing electronic and chirooptical properties of these molecules have attracted scientific interest for decades. The applications of helicenes have now expanded into several fields including material science, nanoscience, biochemistry, supramolecular and polymer chemistry. Despite the great theoretical and practical interest in helicenes, their synthesis remains a challenge. Among synthetic approaches to helicenes, alkyne cyclizations have great potential, since carbon‐rich high‐energy alkynes can form aromatic rings via cycloisomerizations. These processes are atom‐economic. In addition, alkyne reactions are highly favorable thermodynamically. This review focuses on alkyne‐based syntheses of carbo‐ and heterohelicenes (2000–2022). These syntheses are obviously multistage. In the review, they are systematized in terms of the key step leading to the formation of a helical shape. The methods are grouped into two categories: (a) metal‐free syntheses and (b) transition‐metal‐catalyzed syntheses. This division is very arbitrary, since catalytic Sonogashira and Suzuki‐Miyaura reactions and others are often used to prepare starting materials in the syntheses of the first group. Most of the publications on the topic are related to transition‐metal‐catalyzed syntheses of helicenes.

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Inherently Chiral Azonia[6]helicene-Modified β-Cyclodextrin: Synthesis, Characterization, and Chirality Sensing of Underivatized Amino Acids in Water

Abstract: The (P)- and (M)-3-azonia[6]helicenyl β-cyclodextrins exhibit L/D selectivities of up to 12.4 and P/M preferences of up to 28.2 upon complexation with underivatized proteinogenic amino acids in aqueous solution at pH 7.3.

Cited by 61 publications

References 28 publications

Helicene-Based Chiral Auxiliaries and Chirogenesis

Helicene-Based Chiral Auxiliaries and Chirogenesis

Chiral Buckybowl Molecules

Alkyne‐Based Syntheses of Carbo‐ and Heterohelicenes

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