Consecutive chirality transfer: efficient synthesis of chiral C,O-chelated BINOL/gold(iii) complexes for asymmetric catalysis and chiral resolution of disubstituted BINOLs.

A novel approach for efficient synthesis of chiral C,O-chelated BINOL/gold(iii) complexes by diastereomeric resolution using enantiopure BINOL as a chiral resolving agent was demonstrated. The BINOL/gold(iii) diastereomers with different solubility were separated by simple filtration, providing optically pure BINOL/gold(iii) complexes with up to >99 : 1 dr. By combining this with an efficient BINOL ligand dissociation process, a simple and column-free method for chiral resolution of racemic gold(iii) dichloride complexes on a gram scale was established, affording their enantiopure forms in good yields.

Isoindolium-Based Allenes: Reactivity Studies and Applications in Fluorescence Temperature Sensing and Cysteine Bioconjugation.

The reaction of a series of electron-deficient isoindolium-based allenes with sulfhydryl compounds has been studied, leading to the formation of isoindolium-based vinyl sulfides. The vinyl sulfides generated could be readily converted into the corresponding indanones and amines upon heating at 30-70 °C with good yields up to 61 %. The thermal cleavage reaction of vinyl sulfides was further studied for developing temperature-sensitive systems.

A highly selective quinolizinium-based fluorescent probe for cysteine detection.

A novel fluorescent quinolizinium-based turn-off probe has been developed for selective detection of cysteine. The probe showed high selectivity and sensitivity towards cysteine over other amino acids including the similarly structured homocysteine and glutathione with a detection limit of 0.18 μM (S/N = 3).

Functionalized quinolizinium-based fluorescent reagents for modification of cysteine-containing peptides and proteins.

A series of quinolizinium-based fluorescent reagents were prepared by visible light-mediated gold-catalyzed -difunctionalization between quinolinium diazonium salts and electron-deficient alkyne-linked phenylethynyl trimethylsilanes. The electron-deficient alkynyl group of the quinolizinium-based fluorescent reagents underwent nucleophilic addition reaction with the sulfhydryl group on cysteine-containing peptides and proteins. The quinolizinium-based fluorescent reagents were found to function as highly selective reagents for the modification of cysteine-containing peptides and proteins with good to excellent conversions (up to 99%).