By covalent combination of a chiral amino acid, lipid, and achiral phenothiazine derivative, a reaction-based chiroptical probe, PTZ-D, was obtained. PTZ-D could self-assemble into a chiral organogel realizing the chirality transformation from a chiral amino acid to a self-assembled system and displaying unprecedented chiroptical monitoring of ClO- with switchable CPL signals.
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http://dx.doi.org/10.1039/c9cc05245c | DOI Listing |
Angew Chem Int Ed Engl
September 2024
Department of Chemistry, Georgetown University, Washington, DC-20057, USA.
A reaction-based optical relay sensing strategy that enables accurate determination of the concentration and enantiomeric ratio (er) of challenging chiral alcohols exhibiting stereocenters at the α-, β-, γ- or even δ-position or hard-to-detect cryptochirality arising from H/D substitution is described. This unmatched application scope is achieved with a conceptually new sensing approach by which the alcohol moiety is replaced with an optimized achiral sulfonamide chromophore to minimize the distance between the covalently attached chiroptical reporter unit and the stereogenic center in the substrate. The result is a remarkably strong, red-shifted CD induction that increases linearly with the sample er.
View Article and Find Full Text PDFMacromol Rapid Commun
November 2023
Department of Pharmaceutical Engineering, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama, 939-0398, Japan.
The development of peptidomimetics to modulate the conformational profile of peptides has been extensively studied in the fields of biological and medicinal chemistry. However, large-scale synthesis of peptidomimetics with both an ordered sequence and a controlled secondary structure is highly challenging. In this paper, the framework of peptidomimetics has been designed to be alternating an achiral α,α-disubstituted α-amino acid unit and a chiral α-methylphenylalanine unit.
View Article and Find Full Text PDFChem Commun (Camb)
September 2019
Cancer Centre and Centre of Reproduction, Development and Aging, Faculty of Health Sciences, University of Macau, Macau SAR, China.
By covalent combination of a chiral amino acid, lipid, and achiral phenothiazine derivative, a reaction-based chiroptical probe, PTZ-D, was obtained. PTZ-D could self-assemble into a chiral organogel realizing the chirality transformation from a chiral amino acid to a self-assembled system and displaying unprecedented chiroptical monitoring of ClO- with switchable CPL signals.
View Article and Find Full Text PDFChem Commun (Camb)
July 2019
Cancer Centre, Faculty of Health Sciences, University of Macau, Macau SAR, China.
This contribution describes an efficient approach to constructing chiral spiro[pyrrol-benzopyran] (SPP) scaffold with high asymmetry. By combining chiral SPP and the achiral sensing moiety phenothiazine, the target probe P showed unprecedented reaction-based chiroptical sensing towards hypochlorite with switching CD signals.
View Article and Find Full Text PDFJ Am Chem Soc
September 2012
School of Food Science and Technology, State Key Lab of Food Science and Technology, Jiangnan University, Wuxi, JiangSu 214122, People's Republic China.
Chirality at the nanometer scale represents one of the most rapidly developing areas of research. Self-assembly of DNA-nanoparticle (NP) hybrids enables geometrically precise assembly of chiral isomers. The concept of a discrete chiral nanostructure of tetrahedral shape and topology fabricated from four different NPs located in the corners of the pyramid is fundamental to the field.
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