Glycosyl Methanesulfonates in Regio- and Stereoselective Glycosylations Catalyzed by Borinic Acids PDF Download
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Author: Kyan Anthony D'Angelo
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
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Book Description
Stoichiometric and catalytic activation of unprotected glycosyl acceptors toward reaction with glycosyl donors represent a growing breadth of methodologies recently developed with the goal of simplifying the synthesis of important carbohydrate targets. Most of these methods rely on glycosyl halides, a class of donor which has been essentially deprecated in recent literature by the advent of more convenient and versatile species. This report describes the development and use of glycosyl methanesulfonates in borinic acid-catalyzed glycosylations of partially protected acceptors. Good to high yields and selectivities for 1,2-trans-linked disaccharides are obtained without the need for a participating group. Studies of glycosylations with variously protected and configured donors and acceptors suggest wide applicability of the method to the preparation of important classes of linkages and protecting group patterns. Finally, mechanistic insights from NMR observation of the intermediate methanesulfonates are reported and discussed to develop a rationale for the observed catalyst-controlled stereoselectivity.
Author: Kyan Anthony D'Angelo
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
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Book Description
Stoichiometric and catalytic activation of unprotected glycosyl acceptors toward reaction with glycosyl donors represent a growing breadth of methodologies recently developed with the goal of simplifying the synthesis of important carbohydrate targets. Most of these methods rely on glycosyl halides, a class of donor which has been essentially deprecated in recent literature by the advent of more convenient and versatile species. This report describes the development and use of glycosyl methanesulfonates in borinic acid-catalyzed glycosylations of partially protected acceptors. Good to high yields and selectivities for 1,2-trans-linked disaccharides are obtained without the need for a participating group. Studies of glycosylations with variously protected and configured donors and acceptors suggest wide applicability of the method to the preparation of important classes of linkages and protecting group patterns. Finally, mechanistic insights from NMR observation of the intermediate methanesulfonates are reported and discussed to develop a rationale for the observed catalyst-controlled stereoselectivity.
Author: Clay S. Bennett
Publisher: John Wiley & Sons
ISBN: 3527696245
Category : Science
Languages : en
Pages : 500
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Book Description
A comprehensive summary of novel approaches to the stereoselective construction of glycosidic linkages, covering modern glycosylation methods and their use and application in natural product synthesis and drug discovery. Clearly divided into five sections, the first describes recent advances in classical methodologies in carbohydrate chemistry, while the second goes on to deal with newer chemistries developed to control selectivity in glycosylation reactions. Section three is devoted to selective glycosylation reactions that rely on the use of catalytic promoters. Section four describes modern approaches for controlling regioselectivity in carbohydrate synthesis. The final section focuses on new developments in the construction of "unusual" sugars and is rounded off by a presentation of modern procedures for the construction of glycosylated natural products. By providing the latest advances in glycosylation as well as information on mechanistic aspects of the reaction, this is an invaluable reference for both specialists and beginners in this booming interdisciplinary field that includes carbohydrate chemistry, organic synthesis, catalysis, and biochemistry.
Author: Alexei V. Demchenko
Publisher: John Wiley & Sons
ISBN: 3527621652
Category : Science
Languages : en
Pages : 524
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Book Description
Since carbohydrate oligomers are still a challenge in synthetic chemistry, this book on recent developments fulfils a great need. Covering the chemistry necessary to synthesize exact copies of these structures, top authors from all around the world comprehensively deal with synthesis from anomeric halides, from miscellaneous glycosyl donors, and by indirect and special methods, as well as 1-oxygen-and 1-sulfur-substituted derivatives. They demonstrate the best approach for the stereoselective formation of the intermonomeric bond, making this essential reading for every biochemist working in biosynthesis, the exploration of biopathways and vaccines.
Author: Robert Massey Ward
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
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Book Description
Glycosphingolipids (GSLs) have become of increased interest due to recent realization that they may place a role in neurological diseases and cancer. Chemical synthesis of GSLs from simple building blocks requires efficient, yet selective methods to develop the major two components: ceramide and the carbohydrate. Much effort has been done to develop synthesis of the individual components; however the construction of the O-glycosidic bond that connects them has been plagued with regio- and stereoselectivity issues. In the past, both the ceramide and carbohydrate had to be chemically modified for the glycosylation step to occur with good selectivity and yields, but recently unprotected ceramides have been used with protected donors. Borinic acid catalysis has been an important advance in this field, allowing for higher yields and excellent Î ̨-selectivity to develop GSLs. This thesis describes the synthesis of various ceramide derivatives and their corresponding glycosylation by borinic acid catalysis.
Author: Valdir Cechinel Filho
Publisher: Springer
ISBN: 3030005453
Category : Science
Languages : en
Pages : 531
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Book Description
This book addresses the highly relevant and complex subject of research on drugs from natural products, discussing the current hot topics in the field. It also provides a detailed overview of the strategies used to research and develop these drugs. Respected experts explore issues involved in the production chain and when looking for new medicinal agents, including aspects such as therapeutic potential, functional foods, ethnopharmacology, metabolomics, virtual screening and regulatory scenarios. Further, the book describes strategic methods of isolation and characterization of active principles, biological assays, biotechnology of plants, synthesis, clinical trials and the use of tools to identity active principles.
Author: Osama M. Musa
Publisher: John Wiley & Sons
ISBN: 1119468736
Category : Science
Languages : de
Pages : 2665
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Book Description
HANDBOOK OF PYRROLIDONE AND CAPROLACTAM BASED MATERIALS Brings together, for the first time, a comprehensive review of all aspects of pyrrolidone- and caprolactam-based materials This comprehensive, six-volume set describes the broad technical universe of γ- and ε- lactams, reviewing in-depth the chemistry of the small lactam-based molecules, uncovering their unique properties and showing how they have enabled a myriad of commercially important applications. From synthesis, through production and into applications, this extensive work targets significant and recent trends in γ- and ε-lactam science and technology and addresses all key aspects of pyrrolidone- and caprolactam-based materials to produce a definitive overview of the field. Handbook of Pyrrolidone and Caprolactam Based Materials provides a detailed and modern portrait of the impact of pyrrolidone- and caprolactam-based materials on the world, as well as potential future possibilities. Volume One presents the chemistry of small lactam-based molecules and uncovers their unique properties. Volume Two covers polymeric materials, including polyvinyl pyrrolidone and polyvinyl caprolactam, and reviews homopolymerization, copolymerization, controlled radical polymermization and acrylate based pyrrolidone polymerizations. Volume Three examines the physical chemistry and molecular interactions of pyrrolidone and caprolactam based materials. Volume Four expands upon the characterization theme from the third volume, and includes detailed discussions of nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, thermal and mechanical properties, and imaging techniques. Volume Five explores pharmaceutical applications in both ingredients and materials, as well as the antimicrobial properties and applications of pyrrolidone and caprolactam-based materials, and their toxicology. Volume Six covers personal and home care, skin care, transdermal applications and wound care, oral care, adhesion related applications and digital applications such as inkjet technology. Handbook of Pyrrolidone and Caprolactam Based Materials will appeal to industrial scientists and engineers interested in polymer development and manufacturing. It will also benefit academic researchers working in the fields of chemistry, materials science, and chemical and process engineering.
Author: A. C. Knipe
Publisher:
ISBN: 9781119288657
Category : Organic reaction mechanisms
Languages : en
Pages : 872
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Book Description
Organic Reaction Mechanisms 2016, the 52nd annual volume in this highly successful and unique series, surveys research on organic reaction mechanisms described in the available literature dated 2016. The following classes of organic reaction mechanisms are comprehensively reviewed: * Reaction of Aldehydes and Ketones and their Derivatives * Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives * Oxidation and Reduction * Carbenes and Nitrenes * Nucleophilic Aromatic Substitution * Electrophilic Aromatic Substitution * Carbocations * Nucleophilic Aliphatic Substitution * Carbanions and Electrophilic Aliphatic Substitution * Elimination Reactions * Polar Addition Reactions * Cycloaddition Reactions * Molecular Rearrangements
Author: Sebastien Vidal
Publisher: John Wiley & Sons
ISBN: 3527340106
Category : Science
Languages : en
Pages : 522
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Book Description
A unique overview of the most important protecting group strategies in carbohydrate chemistry Protecting Groups: Strategies and Applications in Carbohydrate Chemistry provides a detailed account of key strategies and methodologies for the protection of carbohydrates. Divided into two parts, the first focuses on groups that are used best to protect a specific position on a carbohydrate. In the second part, specific carbohydrate residues or compounds are discussed in the context of a specific protecting group strategy used to reach the desired regioisomer. This important book: -Features chapters on protecting groups at the primary and secondary positions of carbohydrates -Describes protecting group strategies towards sialic acid derivatives, glycofuranoses, sulfated glycosaminoglycans, and cyclodextrins -Provides information on automated glycan assembly -Includes a chapter on the industrial scale synthesis of heparin analogs Written by a team of leaders in the field, Protecting Groups: Strategies and Applications in Carbohydrate Chemistry is an indispensable guide for academics and industrial researchers interested in carbohydrate and natural product synthesis, pharmaceutical chemistry, and biochemistry.
Author: Olga Garcia-Mancheno
Publisher: John Wiley & Sons
ISBN: 3527348573
Category : Technology & Engineering
Languages : en
Pages : 418
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Book Description
Explores the potential of new types of anion-binding catalysts to solve challenging synthetic problems Anion-Binding Catalysis introduces readers to the use of anion-binding processes in catalytic chemical activation, exploring how this approach can contribute to the future design of novel synthetic transformations. Featuring contributions by world-renowned scientists in the field, this authoritative volume describes the structure, properties, and catalytic applications of anions as well as synthetic applications and practical analytical methods. In-depth chapters are organized by type of catalyst rather than reaction type, providing readers with an accessible overview of the existing classes of effective catalysts. The authors discuss the use of halogens as counteranions, the combination of (thio)urea and squaramide-based anion-binding with other types of organocatalysis, anion-binding catalysis by pnictogen and tetrel bonding, nucleophilic co-catalysis, anion-binding catalysis by pnictogen and tetrel bonding, and more. Helping readers appreciate and evaluate the potential of anion-binding catalysis, this timely book: Illustrates the historical development, activation mode, and importance of anion-binding in chemical catalysis Explains the analytic methods used to determine the anion-binding affinity of the catalysts Describes catalytic and synthetic applications of common NH- and OH-based hydrogen-donor catalysts as well as C-H triazole/triazolium catalysts Covers amino-catalysis involving enamine, dienamine, or iminium activation approaches Discusses new trends in the field of anion-binding catalysis, such as the combination of anion-binding with other types of catalysis Presenting the current state of the field as well as the synthetic potential of anion-binding catalysis in future, Anion-Binding Catalysis is essential reading for researchers in both academia and industry involved in organic synthesis, homogeneous catalysis, and pharmaceutical chemistry.
Author: Howard C. Hang
Publisher: John Wiley & Sons
ISBN: 352734733X
Category : Science
Languages : en
Pages : 806
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Book Description
Advanced Chemical Biology The modern approach to teaching chemical biology Advanced Chemical Biology is organized around the central dogma of life, progressing from genes to proteins and higher-order cellular structures, including core application areas such as imaging, chemical genetics, activity-based protein profiling, and natural product discovery and biosynthesis. Advanced topics and applications in, e. g., microbiology, developmental biology, and neurobiology, are covered in separate sections. Every chapter is homogeneous in style and layout, consisting of a short historical introduction followed by a description of the underlying concepts and a selection of recent examples of how the concept has been turned into practice. The subdivision of the contents into core and supplemental chapters enables a flexible use in teaching, both for a one-semester and a two-semester course. Written by authors and editors coming from the leading scientific institutions that have developed the concepts and technologies for this discipline, Advanced Chemical Biology includes specific information on topics like: DNA function, synthesis and engineering, chemical approaches to genome integrity, and RNA function, synthesis, and probing Chemical approaches to transcription and RNA regulation in vivo, chemical biology of genome engineering, and peptide/protein synthesis and engineering Directed evolution for chemical biology, chemical biology of cellular metabolism, chemical biology of lipids, and protein post-translational modifications Chemical glycobiology, chemical and enzymatic modification of proteins, genetic code expansion, bio-orthogonal chemistry, and cellular imaging With its broad scope and focus on turning concepts into applications, Advanced Chemical Biology is an excellent starting point for anyone entering the field and looking for a guide to the wide range of available methods and strategies that chemical biology has to offer. With a Foreword by Nobel Laureate Carolyn Bertozzi.
