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Author: Marco Brito-Arias
Publisher: Springer Nature
ISBN: 3030978540
Category : Science
Languages : en
Pages : 543
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Book Description
This third edition is a comprehensive and extended study about the best known approaches for preparing the main types of glycosides, covering the classic and more recent glycosylation reactions used for preparing simple and challenging glycosides currently used as potent antiviral and antineoplastic drugs, or fluorogenic substrates used for enzymatic detection in cell biology. Besides, this new edition provides more examples of the glycosidic methodologies followed for preparing complex glycoconjugates such as glycoproteins and glycosphingolipids and gangliosides used as adjuvants or as synthetic vaccines candidates. Also, additional mechanistic evidence is presented for better understanding of the glycosylation reaction, trying to identify the variables mainly depending on protecting and leaving groups, as well as catalyst and reaction condition which altogether directs the anomeric stereo control. A chapter on the glycoside hydrolysis is included in view of the increasing interest in the use of biomass as a natural and renewable source for obtaining important intermediates or products used in food or valuable materials. The author includes information in the characterization of glycosides section with the aim of giving additional tools for the structural assignment through NMR, X-Ray and mass spectra techniques.
Author: Marco Brito-Arias
Publisher: Springer Nature
ISBN: 3030978540
Category : Science
Languages : en
Pages : 543
Get Book Here
Book Description
This third edition is a comprehensive and extended study about the best known approaches for preparing the main types of glycosides, covering the classic and more recent glycosylation reactions used for preparing simple and challenging glycosides currently used as potent antiviral and antineoplastic drugs, or fluorogenic substrates used for enzymatic detection in cell biology. Besides, this new edition provides more examples of the glycosidic methodologies followed for preparing complex glycoconjugates such as glycoproteins and glycosphingolipids and gangliosides used as adjuvants or as synthetic vaccines candidates. Also, additional mechanistic evidence is presented for better understanding of the glycosylation reaction, trying to identify the variables mainly depending on protecting and leaving groups, as well as catalyst and reaction condition which altogether directs the anomeric stereo control. A chapter on the glycoside hydrolysis is included in view of the increasing interest in the use of biomass as a natural and renewable source for obtaining important intermediates or products used in food or valuable materials. The author includes information in the characterization of glycosides section with the aim of giving additional tools for the structural assignment through NMR, X-Ray and mass spectra techniques.
Author: Marco Brito Arias
Publisher: Springer
ISBN: 9780387507934
Category : Science
Languages : en
Pages : 0
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Book Description
This book contains the best known approaches for preparing the main types of glycosides in a short and comprehensive study. It also includes synthetic pathways of challenging glycosides known as antiviral or antineoplasic drugs, or synthetic substrates used for enzymatic detection including those used as substrates for detection of gene markers in plant biotechnology. Special attention is made on the structural characterization, providing the basic tools for the structural assignment through NMR, X-Ray and mass spectra techniques. Some of the chapters cover strategies for preparation of antiviral and antineoplasic drugs included in a drug design course.
Author: Michael S. Fisher
Publisher:
ISBN:
Category :
Languages : en
Pages : 322
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Book Description
Author: Maarten Postema
Publisher: CRC Press
ISBN: 1000108554
Category : Science
Languages : en
Pages : 398
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Book Description
This book examines methods particularly well suited for either a- or b-C-glycoside formation. It helps field workers quickly select the best method for synthesizing a particular type of C-glycoside. The use of C-glycosides as synthons in natural product synthesis is also addressed.
Author: Bo Meng
Publisher:
ISBN:
Category : Carbohydrates
Languages : en
Pages : 300
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Book Description
This dissertation presents a state-of-the-art research of 1,2-cis-glycosides, including synthetic methodology development, combinatorial total synthesis of galactoside ligands, construction of glycomicroarray surfaces, and quantitative evaluation of carbohydrate–lectin binding properties. In Chapter 1, as a general introduction, various strategies that have been developed for the stereoselective construction of 1,2-cis-O-glycosidic bond are reviewed. 1,2-cis-O-Glycoside structural units are ubiquitous in nature, and they are extensively involved in numerous biological activities. The systematic identification and evaluation of the roles of carbohydrates usually relies on practical synthetic approaches to afford pure carbohydrates in considerable quantities. Further development of general and efficient approaches to achieve the intrinsic organizational diversity of carbohydrates is still urged in order to meet the substantial carbohydrates in demand for biological, medicinal, and therapeutic studies. In Chapter 2, I report a 1,2-cis-glycosidation protocol that makes use of unprotected phenyl 1-thioglycosyl donors. Glycosylation of various functionalized alcohols was accomplished in moderate to high yield and selectivity to give the 1,2-cis-glycosides. In order to quickly optimize glycosylation conditions, a flow injection analysis method was established that enabled rapid and quantitative evaluation of yield on small scale. This methodology, together with nuclear magnetic resonance spectroscopy, allowed for rapid evaluation of the overall reactions. In Chapter 3, I describe the synthesis of alpha-linked propargyl terminated galactosides with various spatial presentations, which are set to be applied in the construction of synthetic carbohydrate microarrays to mimic featured carbohydrate presentations on a cell surface. Through the routes, glycosyl acceptors were obtained via flexible and efficient regioselective protection strategies, and they were glycosylated with an alpha-directing glycosyl donor to have the alpha-linked galactosides in exclusive stereoselective and satisfactory yield. In Chapter 4, the establishment of a synthetic carbohydrate microarray is described. The carbohydrate surface was interrogated by a fluorescence-labeled lectin to quantitatively analyze the carbohydrate-binding affinities and dissociation constants. This study will add new dimensions to our understanding of the effects of spatial arrangement of carbohydrate ligands in carbohydrate–lectin binding, and shed light on elucidating the structure–affinity relationship of carbohydrate recognition with receptors.
Author: Biao Yu
Publisher: John Wiley & Sons
ISBN: 3527817905
Category : Science
Languages : en
Pages : 309
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Book Description
Carbohydrate Chemistry in the Total Synthesis of Naturally Occurring Glycosides Revolutionize your manufacturing processes and more with this groundbreaking introduction Carbohydrates and complex glycosides are important classes of molecules. The ubiquitous glycosides are extremely diverse in structure and functions, and many of them are of pharmacological significance. Purification of a homogeneous glycoside from the nature sources, especially in an appreciable amount, is always difficult. Chemical synthesis provides a feasible access to the homogenous glycosides and their congeners. Carbohydrate Chemistry in the Total Synthesis of Naturally Occurring Glycosides presents about 10 families of naturally occurring glycoside natural products, including about 150 molecules that organic chemists have devoted a lot of effort toward their synthesis. In each example, the background of each natural glycoside, including its natural resources, its isolation process and its bioactivities have been described; the total synthesis of the natural glycoside is presented with special emphasis on the glycosylation reaction, the strategy on saccharides assembly, the protecting group manipulation, and the method for the synthesis of the rare saccharide units. Readers can clearly see the progress of total synthesis of naturally occurring glycosides, from early to current arts, from simple to complex molecules, and from tedious strategy to highly efficient and economical methodologies in this book. It will highly benefit the further developments in the total synthesis of naturally occurring glycosides and synthetic carbohydrate chemistry. Carbohydrate Chemistry in the Total Synthesis of Naturally Occurring Glycosides is ideal for Organic Chemists, Biochemists, Pharmaceutical and Medicinal Chemists, Natural Products Chemists, and Pharmaceutical Industry
Author: Nan Wang
Publisher:
ISBN:
Category :
Languages : en
Pages : 224
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Author:
Publisher:
ISBN:
Category : Dissertations, Academic
Languages : en
Pages : 206
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Book Description
This thesis describes an investigation of the synthetic approaches to series of novel chalcone glycosides derivatives (compounds 80a, 88a-c, 90a-c and 82b). Chalcones bearing long paraffinic chhains of C7-C9 (Compounds 79a-c and 81a-c), which are the aglycone moiety of these glycosides were initially synthesized via Claisen-Schmidt condensation reaction. The synthesized series of chalcones were then incorporated onto glucal via glycosylation reaction. varying reaction conditions such as temperature and solvents were proved to generate different types og glycosidic bondings in the synthesized chalcone glycosides. an approach using O->C rearrangement was introduced via modification on the temperature.
Author: Maarten H. D. Postema
Publisher:
ISBN:
Category : Glycosides
Languages : en
Pages : 379
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Book Description
Author:
Publisher:
ISBN:
Category :
Languages : en
Pages :
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