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Keywords: Boronic Acid, Sensor, Saccharides.
Boronic acid functional group is used widely as a recognition moiety for the development of sensors for saccharides, due to its unique strong and reversible interaction with diols. The fluorescence and/or UV spectroscopic method are the easiest and most common methods to signal the binding event of these receptors (boronic acid compounds) with saccharides. This dissertation consists of three major parts. First, a series of fluorescent diboronic acid compounds with an anthracene PET (photoinduced electron transfer) system were designed and synthesized (Chapter 1). These compounds can be used as sensors for cell surface carbohydrates, such as sialyl Lewis X (sLex), which are known to be biomarkers for certain cancers. Among these diboronic acid compounds, the lead compound was found to fluorescently label cells expressing sLex selectively. The structure of the lead compound was modified and new conformationally constrained analogs were synthesized. Second, the mechanism of the fluorescent photoinduced electron transfer (PET) system, which was used in our design of fluorescent sensors for sLex, was examined in detail using both density functional calculation (DFT) and model compound fluorescence studies. Based on the study, a new hydrolysis mechanism was proposed (Chapter 2 and 3). Third, novel nitrophenol-based boronic acid reporter compounds, which show significant UV spectroscopic changes upon addition of sugars at neutral pH in aqueous solution, were designed and synthesized (Chapter 4). The design took advantage of the ability of a boronic acid functional group to modulate the pKa and/or the electron density of a neighboring group. These reporter compounds can be used as the recognition and signaling unit for the construction of polyboronic acid sensors for selective and specific recognitions of saccharides of biological significance.
This book contains contributions from interdisciplinary scientists to collectively address the issue of targeting carbohydrate recognition for the development of novel therapeutic and diagnostic agents. The book covers (1) biological problems involving carbohydrate recognition, (2) structural factors mediating carbohydrate recognition, (3) design and synthesis of lectin mimics that recognize carbohydrate ligands with high specificity and affinity, and (4) modulation of biological and pathological processes through carbohydrate recognition.
An essential reference for any laboratory working in the analytical fluorescence glucose sensing field. The increasing importance of these techniques is typified in one emerging area by developing non-invasive and continuous approaches for physiological glucose monitoring. This volume incorporates analytical fluorescence-based glucose sensing reviews, specialized enough to be attractive to professional researchers, yet appealing to a wider audience of scientists in related disciplines of fluorescence.
The desire to quantify the presence of analytes within diverse physiological, environmental and industrial systems has led to the development of many novel detection methods. In this arena, saccharide analysis has exploited the pair-wise interaction between boronic acids and saccharides. Boronic Acids in Saccharide Recognition provides a comprehensive review and critical analysis of the current developments in this field. It also assesses the potential of this innovative approach, outlining future lines of research and possible applications. Topics include: the molecular recognition of saccharides, the complexation of boronic acids with saccharides, fluorescent sensors and the modular construct of fluorescent sensors, further sensory systems for saccharide recognition and an extensive bibliography. This high level book is ideal for researchers both academic and industrial who require a comprehensive overview of the subject.
Carbohydrates are known to play a large number of significant roles in various biological and pathological processes such as cancer metastasis and cellular communication. This is because of their ability to bind a wide range of biological receptors such as proteins and viruses. Due to these important interactions, carbohydrate sensing has long been a main focus of research. These research strategies have included the use of aptamers, non-covalent interactions, and boronic acid-based receptors. Boronic acid-based sensors are of particular interest due to their selectivity for 1,2- or 1,3-diols. Within these boronic acid-based studies, a large variety of techniques were employed for detection including different fluorescent, electrochemical, polymeric, and colorimetric studies, as well as various surface bound sensors. One type of technique that has rarely been applied is Surface Enhanced Raman Spectroscopy or SERS. This strategy would be beneficial as it provides information about functional groups, which would aid in the identification of the bound sugar. In this thesis, we present work based on the development of a boronic acid-based carbohydrate receptor that will be used to study carbohydrate binding through SERS. The receptor design includes an aryl boronic acid for carbohydrate recognition, a nitrogen atom in close proximity to the boron center to enhance binding, and a terminal thiol for attachment to a metal surface for SERS. This sensor will be used to study the binding of different saccharides for sensing applications.
The main objective of the work presented in this thesis was to develop new methods for sugar sensing as well as sugar analysis. Boronic acids were chosen as sugar binding motif because of their affinity to sugars. For this purpose a novel type of boronic acid, 3-Pyridinylboronic acid (3pa), was developed. This boronic acid was identified as a key sensing element for reversible sugar complexation in an aqueous solution at physiological pH. In terms of sugar sensing, 3pba was successfully applied to develop a surface-enhanced Raman glucose sensor. In this study, indirect detection of glucose was demonstrated for the first time by using surface-enhanced Raman spectroscopy. Then, taking advantage of the high binding constant of 3pba with sugars, colorimetric detections of monosaccharides were done using absorption spectroscopy in the visible region. The mechanism of the high diol/triol binding of 3pba in a neutral pH was discussed based on the 1H, 13C, and 11B NMR spectroscopic studies. Monosaccharides as well as disaccharides were explored and K constants were verified by the NMR spectroscopy technique. In terms of sugar analysis, 3pba was used to develop an effective ionization agent for ESI-MS analysis of sugars. It was demonstrated that the dynamic covalent supramolecular binding, between the arylboronic acid and sugars allowed convenient in situ derivatization of the sugar analytes. The zwitterionic nature of 3pba allowed intense ion signals of both the corresponding cations and anions to be observed by a simple switching of the ESI-MS polarity. Isomeric monosaccharides, such as fructose, glucose, and galactose, and isomeric disaccharides, such as lactose and sucrose, were ionized and distinguished by a simple ESI-MS2 experiment. Moreover, zwitterionic aryl boronic acid allowed the facile formations of structurally well-defined gas phase ions with inert charge sites on trisaccharides. As a consequence, successful demonstration of sequencing of a trisaccharide was achieved.
For the first time, the whole field of organoboronic acids is presented in one comprehensive handbook. Professor Dennis Hall, a rising star within the community, covers all aspects of this important substance class, including applications in chemistry, biology and medicine. Starting with an introduction to the structure, properties, and preparation of boronic acid derivatives, together with an overview of their reactions and applications, the book goes on to look at metal-catalyzed borylation of alkanes and arenas, coupling reactions and rhodium-catalyzed additions of boronic acids to alkenes and carbonyl compounds. There follows chapters on copper-promoted C-O and C-N cross-coupling of boronic acids, recent applications in organic synthesis, as well as alpha-haloalkylboronic esters in asymmetric synthesis. Later sections deal with cycloadditions, organoboronic acids, oxazaborolidines as asymmetric inducers, and boronic acid based receptors and sensors. The whole is rounded off with experimental procedures, making this invaluable reading for organic, catalytic and medicinal chemists, as well as those working in organometallics.
Recognition of sugars such as glucose with phenylboronic acid- erminated self assembled monolayers (SAMs) was the basis for the designing and fabricating a biosensor. Self-assembled monolayers were formed on gold surfaces as shown by infrared spectroscopy. The continuous, repeatable increase of the electrochemical impedance as the concentration of glucose was increased gave indication of binding. This binding could be attributed to the precedent formation of relatively stable esters between phenylboronic acids and sugars. This impedance change upon binding between glucose and a phenylboronic acid-terminated SAM showed promise in the development of a glucose biosensor.