Download or read book Carbohydrate based Synthetic Methodology and Polymer Development written by Vishwanath Venkatesh Gaitonde and published by . This book was released on 2015 with total page 165 pages. Available in PDF, EPUB and Kindle. Book excerpt: Carbohydrates are some of the most abundant organic molecules on earth. They are ubiquitous compounds, most commonly known for providing energy for working and are biologically stockpiled as glycogen. Modern Era advancement in disciplines of glycomics, glycobiology, and bio-renewable studies has played a pivotal role in generating robust interest in the study of carbohydrate chemistry. The advances in the field have progressed to cover an expansive range of scientific areas. For example, there is strong interest in i) developing synthetic methodology, ii) understanding reactivity, iii) performing structural studies, iv) exploring enzyme catalysis, v) biological and medical applications, as well as exploiting their use in food and polymer industries. From a biological perspective it is recognized that carbohydrates play a fundamental role in cell recognition, cell-cell interaction, cell differentiation, cell growth, survival of living cells and organisms. Synthetically, a variety of natural products and antibiotics contains carbohydrate moieties, providing a vast platform for glyco-based synthesis. In addition, biochemical inquiries over last few decades have established the association of carbohydrates with various disease conditions and identified glycan(s) as untapped tools in drug discovery. Development of the carbohydrate-based drug discovery can be categorized by one of the following approaches. i) producing native glycans with desired biological activity, ii) structural modification via glycomimetic approaches, iii) generating a glyco-scaffold for achieving carbohydrate diversity, and iv) developing glyco-fused therapeutics. The scope of work covered in this dissertation covers several carbohydrate-related areas. First, we desired to i) develop a series of ß-glycosyl amide linkages demonstrating the use of ß-glycosyl-2,4-dinitrobenzenesulfonamides as key intermediates in the chemoselective formation of these motifs, ii) produce glycosyl fluoride moieties to study their potential inhibitory activity against Mycobacterium tuberculosis (Mtb) GlgE, iii) generate oligosaccharides to study their interaction with the glucan binding site of Mtb GlgE, and iv) demonstrate the utilization of furfural (degradation product of pentose sugars from hemicellulose, bio-resource) to access a bisfuran monomer, in order to generate furan based polymeric materials. Glycosyl amide linkages are key motifs found in glycosyl amino acids, N-linked glycopeptides besides several natural products. Some of the popular strategies to access these linkages include Lansbury aspartylation involving direct coupling of glycosylamine with activated aspartic acid on protected amino acid. Alternatively, a route to access ß-glycosyl amide linkage is via Staudinger reduction-acylation or traceless Staudinger ligation of ß-glycosyl azide. This method ends up producing a mixture of a/ß glycosyl amides. 2,4-Dinitrobenzenesulfonyl chloride (dNBS-Cl) has been used to protect the primary amines producing the 2,4-dinitrobenzenesulfonamides (dNBS-NH2, dNBS). dNBS can be used to produce secondary amines and diamines as noted by Fukuyama et al. dNBS were later explored for producing amides, thioamides, ureas, and thioureas, and only very recently this strategy has been taken as a possible chemoselective approach to form peptide linkage and neoglycoconjugates. To further this chemistry in our chemoselective studies producing the ß-glycosyl amides, we explored the scope of this methodology by reacting a series of ß-dNBS glycosides with thioacetic acid. The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected ß-glycosyl azides. The azides were i) reduced with Adams' catalyst to the corresponding amines, ii) the glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to form N-glycosyl-2,4-dinitrobenzenesulfonamides in moderate yields, and iii) the ß-glycosyl amides were then prepared in 67 - 81 % yields by treatment of the sulfonamides with thioacetic acid and cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity. A second project area involved new approaches to preapare oligosaccharide. Mtb is the causative agent of tuberculosis (TB), which is one of the leading cause of death due to an infectious disease. Designing susbtrates, inhibitors and biochemical probes to understand and overcome this disease condition is of significant interest. Mtb GlgE an a-1,4-glucan: phosphate maltosyltransferase is a genetically validated tuberculosis target. Underlining this target, we designed glycosyl fluoride derivatives, as biochemical probes to determine the active-site residues and better understand the Mtb GlgE catalytic mechanism. 5-fluoro-L-idosyl fluoride, an epimer of 5-fluoro-D-glucosyl fluoride has been synthesized over 5-steps. Starting with D-glucose a key step was photobromination at the C-5 using NBS and AIBN followed by substituting the bromide with fluoride using AgF. Mtb GlgE transfers the maltosyl units on to the elongating the a-1,4-glucan polymer. As a concurrent project we sought to access the oligosaccharide units mimicking the a-glucan polymer in the Mtb GlgE. The oligosaccharides are envisioned to be useful for probing the a-glucan binding site. During the oligosaccharide synthesis, we propose a stereoselective glycosylation strategy was pursued applying a preactivation methodology. Starting with D-maltose, the building blocks for the a-1,4-glucan oligosaccharide were accessed via a divergent synthetic route by creating the donor (4',6'-O-benzylidene-ß-maltosyl thioglycoside) and the acceptor (4'-OH-ß-maltosyl thioglycoside) substrates. During synthesis the donor is first accessed, which was further regioselectively reduced at the 4',6'-O-benzylidene to create 4'-OH (non-reducing end), generating the acceptor substrate. Glycosylation between the donor and acceptor substrate is then envisioned to proceed using a [2+2] preactivated method to build the tetrasachharide unit. This tetrasaccharide on regioselective reduction at the 4',6'-O-benzylidene creates the 4'-OH (non-reducing end), which then acts as a template to produce [4+2] hexasaccharide and/or [4+4] octasaccharide, and so on to access a-1,4-glucan oligosaccharide units of desired length. In a final area of research, carbohydrates were explored as feedstocks for polymer synthesis Starch is commonly understood as a first generation biorenewable feedstock and lignocellulose as second generation biorenewable. Lignocellulose consists of cellulose (40 -- 45 %), hemicellulose (24 -- 40 %), and lignin (18 -- 25 %). Hemicellulose consists chiefly of the pentose sugar xylose and arabinose. The degradation of these pentose sugars yields furfural. The latter is considered to be a leading candidate for bio-renewable building blocks and as a platform chemical for its application in diverse commercial sectors. In the same direction there is a substantial interest and progress in the utilization of this bio-based feedstock to fulfill the growing demands in the sector of fuel, chemical, pharmaceutical and polymer industries. As a part of our preliminary investigation, starting with commercial furfural, we have designed a four steps synthetic route to access a bisfuran diol (BFD) as a monomer feedstock to generate polymeric materials. Starting with commercial furfural i) reaction with 1,2-ethanedithiol in recyclable glycerol produced the 1,3-dithiane protected furfural in 93 % yield after distillation, ii) treatment with acetone and 50% aqueous sulfuric acid produced a dimerized Friedel Crafts product in 58% yield, iii) deprotection of the 1,3-dithiane was accomplished using selenium dioxide along with acetic acid to generate dialdehyde in 90% yield, and iv) the penultimate dialdehyde was reduced to afford the final diol, the BFD in 96 % yield. BFD was crystallized in the monoclinic space group and X-ray studies were undertaken to understand the molecular arrangement in space, hydrogen bonding and packing of the molecule. These set of data were compared with Bisphenol A (BPA, a known endocrine disruptor), and its known derivatives to predict the potential estrogenic or anti-estrogenic activities in BFD. Further, BFD was employed in polymerization studies to successfully generate bisfuran polyester (BFPE-1), a low-molecular weight novel polyester material of amorphous nature.

Download or read book Synthetic Strategies in Carbohydrate Chemistry written by Vinod Kumar Tiwari and published by Elsevier. This book was released on 2023-11-01 with total page 775 pages. Available in PDF, EPUB and Kindle. Book excerpt: Synthetic Strategies in Carbohydrate Chemistry covers carbohydrate synthesis and its widespread application in various disciplines including catalysis. Basic and advanced aspects of carbohydrates are covered, starting with a brief introduction and then followed by protection-deprotection strategies in carbohydrate chemistry, glycosidic bond formation methodology, and their impact in oligosaccharide synthesis. Recent synthetic approaches for O-glycosides, N-glycosides, thioglycosides and C-glycosides, Intramolecular Aglycon Delivery (IAD), and carbohydrate modification are discussed, as well as stereoelectronic factors that control the chemical and biochemical behavior of carbohydrates in living cells. In addition, diverse applications of synthetic carbohydrate chemistry are covered, including sugar-based chiral catalyst in stereoselective synthesis, sugar-based ionic liquids, one-pot tandem reactions in carbohydrates, total synthesis of glycoconjugated natural products, impact of sugar in drug discovery and development, vaccine development, and glycoengineering. This reference is essential reading for researchers working in synthetic carbohydrate chemistry and biochemistry, and will be useful to those working in total synthesis, novel synthetic methodology, catalysis, polymer science, glycobiology, medicinal chemistry, and process development chemistry. Presents a practical and detailed overview on glycosylation methodology Covers automated glycosylation strategies in glycan synthesis Includes recent progress in the synthesis and significance of diverse thio-glycosides, C-glycosides, imino sugars and carbasugars Highlights the impact of enzymes in glycan synthesis Discusses the recent approaches for the synthesis of neoglycoconjugates

Download or read book Cellulose Based Superabsorbent Hydrogels written by Md. Ibrahim H. Mondal and published by Springer. This book was released on 2019-02-22 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: With the prospect of revolutionizing specific technologies, this book highlights the most exciting and impactful current research in the fields of cellulose-based superabsorbent hydrogels with their smart applications. The book assembles the newest synthetic routes, characterization methods, and applications in the emergent area. Leading experts in the field have contributed chapters representative of their most recent research results, shedding light on the enormous potential of this field and thoroughly presenting cellulose-based hydrogel functioning materials. The book is intended for the polymer chemists, academic and industrial scientists and engineers, pharmaceutical and biomedical scientists and agricultural engineers engaged in research and development on absorbency, absorbent products and superabsorbent hydrogels. It can also be supportive for undergraduate and graduate students.

Download or read book Carbohydrate Chemistry State Of The Art And Challenges For Drug Development An Overview On Structure Biological Roles Synthetic Methods And Application As Therapeutics written by Laura Cipolla and published by World Scientific. This book was released on 2015-07-23 with total page 535 pages. Available in PDF, EPUB and Kindle. Book excerpt: The structural complexity and the synthetic challenges facing glycans have historically hampered efforts to study their multifaceted roles and the application of carbohydrates in drug development. However, in very recent years, new synthetic techniques flanked by the growing knowledge about carbohydrate involvement in physiological and pathological states has spurred renewed interest in the chemistry, biology and therapeutic potentialities of carbohydrates. This book offers an overview of key aspects of carbohydrate biology and chemistry that are fundamental for the design of novel therapeutics. The four-part structure of this book introduces these essential components to life, starting from their structure and biological roles and covering analytical methods and synthesis which pave the way for the development of a wide range of therapeutic applications.Leading experts from around the world are brought together to offer their recent research with the ultimate aim of enlightening the reader on the complex yet exciting field of carbohydrate chemistry. Academic and industrial researchers in structural biology, drug discovery and carbohydrate chemistry will find this book an essential guide to the latest research and future potential of medicinal chemistry.

Download or read book Engineered Carbohydrate Based Materials for Biomedical Applications written by Ravin Narain and published by John Wiley & Sons. This book was released on 2011-03-01 with total page 416 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book addresses the need for a comprehensive book on the design, synthesis, and characterization of synthetic carbohydrate-based polymeric materials along with their biological applications. The first two chapters cover the synthesis and self-assembly of glycopolymers and different techniques for creating these synthetic polymers. Subsequent chapters account for the preparation of block copolymers, branched glycopolymers, glycosurfaces, glycodendrimers, cationic glycopolymers, bioconjugates, glyconanoparticles and hydrogels. While these chapters comprehensively review the synthetic and characterization methods of those carbohydrate-based materials, their biological applications are discussed in detail.

Download or read book Carbohydrate Chemistry written by Pavol Kováč and published by CRC Press. This book was released on 2016-04-19 with total page 464 pages. Available in PDF, EPUB and Kindle. Book excerpt: Long gone are the days when synthetic publications included parallel preparative experiments to document reproducibility of the experimental protocols and when journals required such documentation. The new Proven Synthetic Methods Series addresses concerns to chemists regarding irreproducibility of synthetic protocols, lack of characterization data

Download or read book Carbohydrate based Drug Discovery written by Chi-Huey Wong and published by John Wiley & Sons. This book was released on 2006-03-06 with total page 980 pages. Available in PDF, EPUB and Kindle. Book excerpt: To exploit the full potential of this diverse compound class for the development of novel active substances, this handbook presents the latest knowledge on carbohydrate chemistry and biochemistry. While it is unique in covering the entire field, particular emphasis is placed on carbohydrates with pharmaceutical potential. Topics include the following: > Chemical Synthesis of Carbohydrates > Carbohydrate Biosynthesis and Metabolism > Carbohydrate Analysis > Cellular Functions of Carbohydrates > Development of Carbohydrate-based Drugs A premier resource for carbohydrate chemists and drug developers, this comprehensive two-volume work contains contributions by more than 50 of the world's leading carbohydrate chemists.

Download or read book Glycochemistry written by Peng George Wang and published by CRC Press. This book was released on 2001-06-15 with total page 696 pages. Available in PDF, EPUB and Kindle. Book excerpt: US, Canadian, and Chinese chemists summarize recent research into the synthesis, principles, and applications of carbohydrates for graduate students and researchers in carbohydrate chemistry, biochemistry, medicinal chemistry, and glycobiology. The topics include solid phase oligosaccharide synthesis, the chemical synthesis of bioactive steroidal saponins, the chemistry and biology of multi-valent saccharide displays, structures and mechanisms of action of aminoglycoside antibiotics, synthesizing glycosaminoglycans, glycosyltransferases in oligosaccharide synthesis, and metabolic substrate engineering as a tool for glycobiology Glycochemistry: Principles, Synthesis, and Applications presents methods used in the development of carbohydrate-based therapeutics. It highlights applications in chemical and enzymatic synthesis of complex carbohydrates, carbohydrate function, and carbohydrate-mediated biological recognition processes. There are practical examples on the development of carbohydrate-based pharmaceuticals and polymers for commercial use. The text also emphasizes the role of carbohydrates as key elements in modern molecular recognition processes.

Download or read book Modern Synthetic Methods in Carbohydrate Chemistry written by Daniel B. Werz and published by John Wiley & Sons. This book was released on 2013-12-23 with total page 419 pages. Available in PDF, EPUB and Kindle. Book excerpt: The fields of glycochemistry and glycoscience are rich and varied and where much can be learned from Nature. As Nature is not always able to produce carbohydrates in quantities useful for not only in research but also as therapeutic agents, new ways need to be found to optimize the yield. This book presents an overview of the latest developments in the field of carbohydrates, ranging from de-novo approaches via cyclodextrin chemistry to the synthesis of such highly complex glycoconjugates as glycosphingolipids and GPI anchors. The main emphasis remains on the synthetic aspects making the book an excellent source of information for those already involved in carbohydrate chemistry, as well as for those organic chemists who are beginners in this field. Equally of interest to synthetic chemists, as well as medicinal chemists and biochemists.

Download or read book Carbohydrate Chemistry Volume 45 written by Yves Queneau and published by Royal Society of Chemistry. This book was released on 2021-12-22 with total page 713 pages. Available in PDF, EPUB and Kindle. Book excerpt: Carbohydrate Chemistry is an invaluable volume demonstrating the interdisciplinary nature of modern carbohydrate research and containing analysed, evaluated and distilled information on the latest research in the area.

Download or read book Natural Polymer Drug Delivery Systems written by Saurabh Bhatia and published by Springer. This book was released on 2016-09-23 with total page 235 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book describes 200 bio-polymers, including the most recent and advanced nanotechnology applications. The applications of various bio-medical and other future potential uses are covered and examined in depth. Systematic discussion of current leading natural polymers is also included.

Download or read book Modern Methods in Carbohydrate Synthesis written by Shaheer H. Khan and published by CRC Press. This book was released on 2020-08-26 with total page 580 pages. Available in PDF, EPUB and Kindle. Book excerpt: Modern Methods in Carbohydrate Synthesis presents in one volume a sequence of chapters leading from classical methods through to today's newest state-of -the-art technology for oligosaccharide synthesis. It places particular emphasis on the most recent breakthroughs in the field, including emerging technologies for both oligosaccharide and glycoconjugate synthesis. Chapters describing the synthesis of increasingly important glycosidic linkage analogs, as well as the oligosaccharides containing derivatives and analogs of natural sugars are included. While chemical-synthetic methods constitute the major part of the book, completing the volume is a section on the rapidly expanding and important field of enzymatic synthesis, also covering combined chemical and enzymatic synthesis. Chapters are written by leading experts in the field. Wherever possible, methods of synthesis are provided in sufficient detail to allow the reader to implement the techniques described. More than 1700 references are provided in the 21 chapters comprising the book. This volume should provide a wealth of information to a large number of synthetic organic chemists, medicinal chemists, protein chemists, biochemists, glycobiologists and cell biologists, including students in these fields.

Download or read book Carbohydrate Chemistry written by Christian Vogel and published by CRC Press. This book was released on 2017-09-18 with total page 369 pages. Available in PDF, EPUB and Kindle. Book excerpt: Volumes in the Proven Synthetic Methods Series address the concerns many chemists have regarding irreproducibility of synthetic protocols, lack of identification and characterization data for new compounds, and inflated yields reported in chemical communications—trends that have recently become a serious problem. Featuring contributions from world-renowned experts and overseen by a highly respected series editor, Carbohydrate Chemistry: Proven Synthetic Methods, Volume 4 compiles reliable synthetic methods and protocols for the preparation of intermediates for carbohydrate synthesis or other uses in the glycosciences. Exploring carbohydrate chemistry from both the academic and industrial points of view, this unique resource brings together useful information into one convenient reference. The series is unique among other synthetic literature in the carbohydrate field in that, to ensure reproducibility, an independent checker has verified the experimental parts involved by repeating the protocols or using the methods. The book includes new or more detailed versions of previously published protocols as well as those published in not readily available journals. The essential characteristics of the protocols presented are reliability, updated characterization data for newly synthesized substances and the expectation of wide utility in the carbohydrate field. The protocols presented will be of wide use to a broad range of readers in the carbohydrate field and the life sciences, including undergraduates taking carbohydrate workshops.

Download or read book Carbohydrate based Drug Discovery 2 Volume Set written by Chi-Huey Wong and published by John Wiley & Sons. This book was released on 2003-10-17 with total page 977 pages. Available in PDF, EPUB and Kindle. Book excerpt: To exploit the full potential of this diverse compound class for the development of novel active substances, this handbook presents the latest knowledge on carbohydrate chemistry and biochemistry. While it is unique in covering the entire field, particular emphasis is placed on carbohydrates with pharmaceutical potential. Topics include the following: > Chemical Synthesis of Carbohydrates > Carbohydrate Biosynthesis and Metabolism > Carbohydrate Analysis > Cellular Functions of Carbohydrates > Development of Carbohydrate-based Drugs A premier resource for carbohydrate chemists and drug developers, this comprehensive two-volume work contains contributions by more than 50 of the world's leading carbohydrate chemists.

Download or read book Synthetic Aspects of Aminodeoxy Sugars of Antibiotics written by Istvan F. Pelyvas and published by Springer Science & Business Media. This book was released on 2012-12-06 with total page 256 pages. Available in PDF, EPUB and Kindle. Book excerpt: The synthetic chemistry of carbohydrates has advanced at a scarcely equalled rate in the last 25 years, due to the great interest of biologically active natural products coritaining sugar moieties. It suffices to note that in the review by J. D. Dutcher appearing in "Advances in Carbohydrate Chemistry" vol. 18, 1963, only the structures of less than ten aminodeoxy sugars were reported. This book deals exclusively with a single class of carbohydrates, namely the aminodeoxy sugars of antibiotics, the most popular of which is probably daunosamine, a compound for which more than 20 different synthetic approaches have been reported in the literature since the publication of its structure in 1964. No compound in the 3-amino-2-deoxY-L-hexose series had been prepared by chemical synthesis when we started our synthetic work in this field in 1972 on the wave of the successful therapeutic applications of adriamycin. The compounds with xylo stereochemistry were unknown even in the more easily accessible D-series. The size of this book documents the rapid development of the field. I wish to add that the improvements of chemical methodology reported in. the volume outspan the specific field and are of importance in the design of synthetic approaches to other carbohydrate structures. These also include compounds involved in chemical interactions of great biological interest, but hitherto un explained at the molecular level, such as those related with cell recognition, adhesiveness and differentiation.

Download or read book Carbohydrate Chemistry written by Christian Vogel and published by CRC Press. This book was released on 2017-09-18 with total page 461 pages. Available in PDF, EPUB and Kindle. Book excerpt: Volumes in the Proven Synthetic Methods Series address the concerns many chemists have regarding irreproducibility of synthetic protocols, lack of identification and characterization data for new compounds, and inflated yields reported in chemical communications—trends that have recently become a serious problem. Featuring contributions from world-renowned experts and overseen by a highly respected series editor, Carbohydrate Chemistry: Proven Synthetic Methods, Volume 4 compiles reliable synthetic methods and protocols for the preparation of intermediates for carbohydrate synthesis or other uses in the glycosciences. Exploring carbohydrate chemistry from both the academic and industrial points of view, this unique resource brings together useful information into one convenient reference. The series is unique among other synthetic literature in the carbohydrate field in that, to ensure reproducibility, an independent checker has verified the experimental parts involved by repeating the protocols or using the methods. The book includes new or more detailed versions of previously published protocols as well as those published in not readily available journals. The essential characteristics of the protocols presented are reliability, updated characterization data for newly synthesized substances and the expectation of wide utility in the carbohydrate field. The protocols presented will be of wide use to a broad range of readers in the carbohydrate field and the life sciences, including undergraduates taking carbohydrate workshops.

Download or read book Enzymes in Synthetic Organic Chemistry written by Chi-Huey Wong and published by Elsevier. This book was released on 1994-07 with total page 392 pages. Available in PDF, EPUB and Kindle. Book excerpt: Covering the recent development in enzymatic organic synthesis, this text focuses on the use of isolated enzymes. It includes a discussion of the characteristics of enzymes as catalysts and different types of chemical transformations.