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Traffic Lights for Catalysis: Stimuli-Responsive Molecular and Extended Catalytic Systems.
Angew Chem Int Ed Engl
July 2023
Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC 29208, USA.
The advances made in the field of stimuli-responsive catalysis during the last five years with a focus on the novel recently-emerged directions and applications have been surveyed. Metal-free catalysts and organometallic complexes, as well as biomimetic systems and extended structures, which display switchable catalytic activity for a variety of organic transformations, are discussed. Light-activated systems comprised of photochromic molecules capable of modulating reaction rate, yield, or enantioselectivity based on geometric and electronic changes associated with photoisomerization are the focus of the detailed discussion.
View Article and Find Full Text PDFOn-Demand Chirality Transfer of Human Serum Albumin to Bis(thiophen-2-yl)hexafluorocyclopentenes through Their Photochromic Ring Closure.
J Org Chem
September 2021
Department of Chemistry and Life Science, Graduate School of Engineering Science, Yokohama National University, 79-5, Tokiwadai, Hodogaya, Yokohama 240-8501, Japan.
Photochromic 1,2-bis(5-carboxy-3-methyl-2-thienyl)hexafluorocyclopentene and its dimethyl ester incorporated in human serum albumin (HSA) showed highly enantioselective photochromic ring-closing reactions upon 366 nm light irradiation. The absolute stereochemistry of the major ring-closed form of the dicarboxylic acid at the newly formed sp carbon atoms was determined to be () by the process of docking simulation of the diarylethene molecule and HSA followed by molecular dynamics calculations and comparison of the measured and calculated CD spectra. Esterification of the major closed form of the diacid gave the minor closed form of the diester.
View Article and Find Full Text PDFChiral self-sorted multifunctional supramolecular biocoordination polymers and their applications in sensors.
Nat Commun
September 2018
Department of Chemical Engineering, Pohang University of Science and Technology (POSTECH), Pohang, Gyeongbuk, 37673, Republic of Korea.
Chiral supramolecules have great potential for use in chiral recognition, sensing, and catalysis. Particularly, chiral supramolecular biocoordination polymers (SBCPs) provide a versatile platform for characterizing biorelated processes such as chirality transcription. Here, we selectively synthesize homochiral and heterochiral SBCPs, composed of chiral naphthalene diimide ligands and Zn ions, from enantiomeric and mixed R-ligands and S-ligands, respectively.
View Article and Find Full Text PDFPhotocyclization of photoswitches with high enantioselectivity in human serum albumin in an artificial environment.
Chem Commun (Camb)
March 2017
Department of Advanced Materials Chemistry, Graduate School of Engineering, Yokohama National University, 79-5, Tokiwadai, Hodogaya, Yokohama 240-8501, Japan.
Three photochromic bisthienylethenes exhibited 56 to >99% enantiomeric excess in photochemical ring closure upon UV irradiation when incorporated in human serum albumin dissolved in 15% acetonitrile-phosphate buffer solution and incubated for 24 h at -4 °C. The absolute stereochemistry of the major enantiomers of two bisthienylethenes has been determined by their chemical transformations.
View Article and Find Full Text PDFDynamic Inversion of Stereoselective Phosphate Binding to a Bisurea Receptor Controlled by Light and Heat.
Angew Chem Int Ed Engl
January 2016
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
A chiral bisurea anion receptor, derived from a first-generation molecular motor, can undergo photochemical and thermal isomerization operating as a reconfigurable system. The two possible cis configurations in the isomerization cycle are opposite in helicity, as is shown by CD spectroscopy. (1)H NMR titrations demonstrate that the P and M helical cis isomers hold opposite enantioselectivity in the binding of binol phosphate, while anion complexation by the intermediate trans isomer is not selective.
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