Amino acid based chiral N-amidothioureas. Acetate anion binding induced chirality transfer

Fang, Wang; He, Wen-Bin; Wang, Jinhe; Yan, Xiaosheng; Zhan, Ying; Ma, Yingying; Ye, Li-Cai; Yang, Rui; Cai, Fu; Zhao, Li

doi:10.1039/c1cc14995d

Cited by 11 publications

(5 citation statements)

References 39 publications

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“…The resultant opposite and coupled Cotton effects at 304 nm and 270 nm suggest that the chirality of the phenylthiourea moiety in 2 has been overturned and extended to the anion-thiourea binding block. 7 The mirror-imaged CD spectra of AcO À -L-2 and AcO À -D-2 solutions (Fig. 3) again confirm that the chirality originates from the phenylalanine residue.…”

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confidence: 58%

“…S1, ESI †). 7 The thiourea moiety in 2 is thus turned chiral by simply capping 1 with an achiral glycine residue (Scheme 2), which demonstrates the key role that the glycine residue in 2 plays in facilitating the intramolecular chirality transfer, despite its achiral nature and its distance from the thiourea moiety.…”

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confidence: 97%

“…5 Given the structural similarity of thioamide to oxoamide, 6 we envisaged that within the peptide-based N-amidothioureas the b-turn structure might be created if the thioureido -NH is designed to act as a hydrogen bonding donor. Here we report our first attempt by capping the amino acid based N-amidothioureas (1, Scheme 2), 7 with a simple achiral glycine residue at the N-terminal of the amino acid residue in 1. Thus created glycinylphenylalanine dipeptide based N-amidothioureas (L-2 and D-2, Scheme 2) were shown to bear a b-turn structure in both solid state and solution phase.…”

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confidence: 99%

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β-Turn structure in glycinylphenylalanine dipeptide based N-amidothioureas

Yan

Yuan

et al. 2013

Chem. Commun.

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confidence: 58%

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confidence: 97%

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confidence: 99%

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β-Turn structure in glycinylphenylalanine dipeptide based N-amidothioureas

Yan

Yuan

et al. 2013

Chem. Commun.

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“…Figure 1D discloses that bSiNPs and gSiNPs exhibit a cotton effect similar to that of L-dopa in 240− 296 nm, which indicates that the above nanomaterials inherited the inherent chirality of L-dopa. The new CD signal at 296−350 nm was generated by the π−π* transition of the aromatic sp 2 domain placed in a chiral environment, 29,30 indicating that chiral bSiNPs and gSiNPs have been successfully fabricated. The absolute quantum yields of the obtained bSiNPs and gSiNPs were 0.3 and 1.9%, respectively.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Enantioselective Glutamic Acid Discrimination and Nanobiological Imaging by Chiral Fluorescent Silicon Nanoparticles

Han,

Kou,

Quan

et al. 2024

Anal. Chem.

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Enantioselective discrimination of chiral molecules is essential in chemistry, biology, and medical science due to the configuration-dependent activities of enantiomers. Therefore, identifying a specific amino acid and distinguishing it from its enantiomer by using nanomaterials with outstanding performance are of great significance. Herein, blue-and green-emitting chiral silicon nanoparticles named bSiNPs and gSiNPs, respectively, with excellent water solubility, salt resistance, pH stability, photobleaching resistance, biocompatibility, and ability to promote soybean germination, were fabricated in a facile one-step method. Especially, chiral gSiNPs presented excellent fluorescence recognition ability for glutamic acid enantiomers within 1 min, and the enantiomeric recognition difference factor was as high as 9.0. The mechanism for enantiomeric fluorescence recognition was systematically explored by combining the fluorescence spectra with density functional theory (DFT) calculation. Presumably, the different Gibbs free energy and hydrogen-bonding interaction of the chiral recognition module with glutamic acid enantiomers mainly contributed to the difference in the fluorescence signals. Most noteworthy was the fact that the chiral gSiNPs can showcase not only the ability to recognize L-and D-glutamic acids in living cells but also the test strips fabricated by soaking gSiNPs can be applied for D-glutamic acid visual detection. As a result, this study provided insights into the design of multifunctional chiral sensing nanoplatforms for enantiomeric detection and other applications.

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“…5, we also found that in addition to retaining the chiral signal of cysteine, a new set of signal peaks appeared at 250 nm, indicating that L-NGQDs and D-NGQDs are inherited and transferred in their structure through chirality, induce the generation of new chiral centers. 30,31 Detection of tartaric acid by linear sweep voltammetry.-Here we synthesize chiral inorganic nanomaterials and use them to identify tartaric acid by voltammetry. It can be known from the theory that tartaric acid ionizes in water, and its existing state is different under different pH values, while tartaric acid only exists when the pH value is lower than 3 when the pH value is higher than 5, it will exist as tartrate anions.…”

Section: Resultsmentioning

confidence: 99%

Chiral Nitrogen-Doped Graphene Quantum Dot Electrochemical Sensor for Recognition of Tartaric Acid Isomers

Pei

Chen

Guo

et al. 2021

J. Electrochem. Soc.

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Chirality is a basic attribute of object in three-dimensional space, and the phenomenon of chirality exists widely in nature. By covalently grafting L/D-cysteine to nitrogen-doped graphene quantum dots (NGQDs) through amide reaction, a new type of chiral NGQDs was obtained. Its morphology was characterized by transmission electron microscope, and its structure and composition were determined by X-ray powder diffraction, infrared spectroscopy, raman spectroscopy, ultraviolet spectroscopy and X-ray photoelectron spectroscopy. In the linear cyclic voltammetry test, it is found that chiral NGQDs have different peak current values in different configurations of tartaric acid, and the changes in the peak current intensity can specifically identify L/D-tartaric acid isomers. There are two identical asymmetric carbon atoms in the tartaric acid molecule, which is a by-product of the wine industry. Due to its low price, it is often used to resolve other racemates, such as epinephrine and chloramphenicol. Through the method of molecular simulation and docking calculation, the combination of chiral graphene quantum dots and tartaric acid was studied, and the mechanism of chiral recognition was discussed. This work broadens the application range of graphene quantum dots and provides new ideas for the preparation of chiral inorganic nanomaterials.

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Amino acid based chiral N-amidothioureas. Acetate anion binding induced chirality transfer

Abstract: N-Amidothioureas generated from amine-dimethylated natural L-phenylalanine and its D-enantiomer bearing a chiral carbon that is by 2 atoms or 3 chemical bonds away from the anion binding site establish chiral communication upon acetate anion binding to the thiourea moiety.

Cited by 11 publications

References 39 publications

β-Turn structure in glycinylphenylalanine dipeptide based N-amidothioureas

β-Turn structure in glycinylphenylalanine dipeptide based N-amidothioureas

Enantioselective Glutamic Acid Discrimination and Nanobiological Imaging by Chiral Fluorescent Silicon Nanoparticles

Chiral Nitrogen-Doped Graphene Quantum Dot Electrochemical Sensor for Recognition of Tartaric Acid Isomers

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