Enantioselective Fluorescent Sensors for <i>N</i>‐Boc‐Protected Amino Acid Anions Based on BINOL

Xu, Kuoxi; Bu, Zhanwei; Huang, Ke-Jing; Zhao, Jin; Wang, Chaojie

doi:10.1002/cjoc.201090150

Cited by 7 publications

(1 citation statement)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chirality is a ubiquitous feature in nature; most biological and chemical reactions are accompanied by changes in chirality. In the last decade, more and more fluorescent probes have been designed for enantioselective recognition [ 1 , 2 , 3 , 4 , 5 , 6 ]. At present, most of the research about the enantioselective recognition of chiral molecules is related to certain chiral amino acids, amino alcohols, α-hydroxycarboxylic acids, and their derivatives.…”

Section: Introductionmentioning

confidence: 99%

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Wang,

Song,

Wei

et al. 2024

IJMS

View full text Add to dashboard Cite

The chiral H8-BINOL derivatives R-1 and R-2 were efficiently synthesized via a Suzuki coupling reaction, and they can be used as novel dialdehyde fluorescent probes for the enantioselective recognition of R/S-2-amino-1-phenylethanol. In addition, R-1 is much more effective than R-2. Scanning electron microscope images and X-ray analyses show that R-1 can form supramolecular vesicles through the self-assembly effect of the π-π force and strong hydrogen bonding. As determined via analysis, the fluorescence of the probe was significantly enhanced by mixing a small amount of S-2-amino-1-phenylethanol into R-1, with a redshift of 38 nm, whereas no significant fluorescence response was observed in R-2-amino-1-phenylethanol. The enantioselective identification of S-2-amino-1-phenylethanol by the probe R-1 was further investigated through nuclear magnetic titration and fluorescence kinetic experiments and DFT calculations. The results showed that this mechanism was not only a simple reactive probe but also realized object recognition through an ICT mechanism. As the intramolecular hydrogen bond activated the carbonyl group on the probe R-1, the carbonyl carbon atom became positively charged. As a strong nucleophile, the amino group of S-2-amino-1-phenylethanol first transferred the amino electrons to a carbonyl carbocation, resulting in a significantly enhanced fluorescence of the probe R-1 and a 38 nm redshift. Similarly, S-2-amino-1-phenylethanol alone caused severe damage to the self-assembled vesicle structure of the probe molecule itself due to its spatial structure, which made R-1 highly enantioselective towards it.

show abstract

Section: Introductionmentioning

confidence: 99%

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Wang,

Song,

Wei

et al. 2024

IJMS

View full text Add to dashboard Cite

show abstract

(S)‐BINOL Immobilized onto Multiwalled Carbon Nanotubes through Covalent Linkage: A New Approach for Hybrid Nanomaterials Characterization

et al. 2015

View full text Add to dashboard Cite

(S)-6-(4-(Methoxycarbonyl)phenyl)-1,1'-bis-2-naphthol, ac hiral 1,1'-bis-2-naphthol (BINOL) derivative, wasp repared via SuzukiC ÀCc oupling and immobilized onto diamine-functionalized multiwalled carbonn anotubes. The BINOL was first derivatized with ac arboxylic acid, capable of forming an amide linkage with the amine-carbon nanotube modified surface. The 4-methoxyphenylboronic acid was replaced by 3-fluoro-4-(methoxycarbonyl)phenylboronic acid and (S)-6-(3-fluoro-4-(methoxycarbonyl)phenyl)-1,1'-bis-2-naphthol was obtained and used as ap robe to better quantify the organic material. It was found that in the hybrid material, 1/3 of amine groups have been transformed into the corresponding amide (S)-BINOL derivative. The chemical and electronic integrity of the chiral BINOL ligand is maintained after the ligand immobilization. Evaluation in diethyl zinc and Ti(OiPr) 4 -catalyzed alkylation of benzaldehyde showed that both methoxycarbonylphenyl andf luoromethoxycarbonylphenyl BINOL moieties do not significantly influence the catalytic activity or selectivity of the process. However,w hen hybridm aterials were used, similar activities were obtained, but with lower enantioselectivities.T his result could be due to ac ompetitive alkylation reactiono ccurring on the carbon surfaceo rb yt he constraint caused by the ligand proximity on the support surface.

show abstract

Novel chiral Oxa-bridged Calix[2]arene[2]triazine derivatives as NMR chiral reagents for enantioselective recognition of α-racemic carboxylic acids

Genc

2019

J Incl Phenom Macrocycl Chem

View full text Add to dashboard Cite

Enantioselective Fluorescent Sensors for N‐Boc‐Protected Amino Acid Anions Based on BINOL

Cited by 7 publications

References 43 publications

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

(S)‐BINOL Immobilized onto Multiwalled Carbon Nanotubes through Covalent Linkage: A New Approach for Hybrid Nanomaterials Characterization

Novel chiral Oxa-bridged Calix[2]arene[2]triazine derivatives as NMR chiral reagents for enantioselective recognition of α-racemic carboxylic acids

Contact Info

Product

Resources

About