Fluorescent Sensor Array for Quantitative Determination of Saccharides.

Accurate monitoring of sugar levels is essential for many fields from food industry to human health. Here, we developed FRET-based dual chromophore sensors for saccharides that form oxazolidine boronate and may be employed as a noninvasive method for monitoring of sugar levels in biological fluids, namely, urine. The saccharide-binding properties of the sensors were studied using fluorescence spectroscopy and utilized in the determination of saccharides in a high-throughput manner. Here, two fluorescent sensors were successful in the classification of nine different monosaccharides and disaccharides with 100% correct classification. Furthermore, the dual chromophore self-assembled sensors were successfully utilized for the quantitative determination of important carbohydrates such as glucose in the presence of competitive saccharides (fructose) and in complex media (urine) without sample pretreatment. The present fluorescent sensors allow for quantification of glucose in a concentration range of 0-60 mM, which matches the concentration range of frequently used urinalysis test strips.

A Fluorescence Sensor Array Based on Zinc(II)-Carboxyamidoquinolines: Toward Quantitative Detection of ATP*.

The newly prepared fluorescent carboxyamidoquinolines (1-3) and their Zn(II) complexes (Zn@1-Zn@3) were used to bind and sense various phosphate anions utilizing a relay mechanism, in which the Zn(II) ion migrates from the Zn@1-Zn@3 complexes to the phosphate, namely adenosine 5'-triphosphate (ATP) and pyrophosphate (PPi), a process accompanied by a dramatic change in fluorescence. Zn@1-Zn@3 assemblies interact with adenine nucleotide phosphates while displaying an analyte-specific response. This process was investigated using UV-vis, fluorescence, and NMR spectroscopy. It is shown that the different binding selectivity and the corresponding fluorescence response enable differentiation of adenosine 5'-triphosphate (ATP), adenosine 5'-diphosphate (ADP), pyrophosphate (PPi), and phosphate (Pi). The cross-reactive nature of the carboxyamidoquinolines-Zn(II) sensors in conjunction with linear discriminant analysis (LDA) was utilized in a simple fluorescence chemosensor array that allows for the identification of ATP, ADP, PPi, and Pi from 8 other anions including adenosine 5'-monophosphate (AMP) with 100 % correct classification. Furthermore, the support vector machine algorithm, a machine learning method, allowed for highly accurate quantitation of ATP in the range of 5-100 µM concentration in unknown samples with error <2.5 %.

A dual chromophore sensor for the detection of amines, diols, hydroxy acids, and amino alcohols.

The determination of enantiomeric excess (ee) in various groups of chiral compounds, namely amines, amino alcohols, diols, and hydroxy acids is performed using a dual chromophore FRET/PET based sensor ensemble. The sensing ensemble utilizes fluorescence changes from two chromophores (indicators) to classify 13 pairs of enantiomers as well as allows for the qualitative and quantitative determination of ee of various classes of chiral compounds with high accuracy (<2% error).

Fluorimetric sensing of ATP in water by an imidazolium hydrazone based sensor.

Bisantrene, a simple anthracene derivative carrying two imidazolium hydrazone moieties, has been used as a highly selective sensor of ATP in water. While bisantrene is not fluorescent in water, it displays a bright green fluorescence (OFF-ON signals) in the presence of ATP and to a lesser extent also ADP but not with other anions. Such selective sensors for ATP in water are still rare.

Cross-Dehydrogenative Coupling Reactions Between P(O)-H and X-H (X = S, N, O, P) Bonds.

P(O)-X (X = S, N, O, P) bond-containing compounds have extensive application in medicinal chemistry, agrochemistry, and material chemistry. These useful organophosphorus compounds also have many applications in organic synthesis. In light of the importance of titled compounds, there is continuing interest in the development of synthetic methods for P(O)-X bonds construction. In the last 4 years, the direct coupling reaction of P(O)-H compounds with thiols, alcohols, and amines/amides has received much attention because of the atom-economic character. This review aims to give an overview of new developments in cross-dehydrogenative coupling reactions between P(O)-H and X-H (X = S, N, O, P) bonds, with special emphasis on the mechanistic aspects of the reactions.

Advancements in six-membered cyclic carbonate (1,3-dioxan-2-one) synthesis utilizing carbon dioxide as a C1 source.

This review article surveys literature methods for the synthesis of six-membered cyclic carbonates using various substrates in the presence of CO2 with special emphasis on the mechanistic aspects of the reactions. We have classified these reactions based on the type of starting material.