Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies.
About: This article is published in Chemical Reviews.The article was published on 2000-10-04. It has received 419 citations till now. The article focuses on the topics: Glycoconjugate.
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TL;DR: New principles for the formation of glycoside bonds are discussed and developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.
Abstract: Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.
741 citations
569 citations
TL;DR: Observations demonstrate that new polymeric materials are often brought about by new production methods including polymerization catalysts, as exemplified typically by the discovery of Ziegler-Natta catalyst.
Abstract: Polymeric materials, natural and unnatural, are indispensable to the modern society. They are widely used from everyday life usages as commodity materials to industry and technology usages in the fields such as electronics, machinery, communications, transportations, pharmacy, and medicine as highly advanced materials. Today, it is hard to think of the present society without polymeric materials. Developments of various polymeric materials have been owed to epoch-making innovative works as exemplified typically by the discovery of Ziegler-Natta catalyst,1-3 the concept of living polymerization,4 the discovery of conducting polymers,5 and the discovery of metathesis catalyst.6,7 These observations demonstrate that new polymeric materials are often brought about by new production methods including polymerization catalysts. Historically, polymerization catalysts utilized classical catalysts of acids (Brønsted acids, Lewis acids, and various cations), bases (Lewis bases and various anions), and radical generating compounds since the 1920s, the early stage of polymer chemistry. In the following * To whom correspondence should be addressed. Fax/Tel: (+81)-75-7247688. E-mail: kobayash@kit.ac.jp. † Kyoto Institute of Technology and Emeritus Professor of Kyoto University. ‡ Kyoto University. Chem. Rev. 2009, 109, 5288–5353 5288
505 citations
TL;DR: This review describes recent changes and progress in the field of polymer bioconjugation, i.e. covalent attachment of synthetic polymers to biological entities such as nucleic acids, oligopeptides, proteins, enzymes, carbohydrates, viruses or cells.
485 citations
TL;DR: The remarkable diversity of techniques available for the construction of glycoproteins is presented and it is unlikely to be enough to "just make it", and in this regard the timing of glycosylation and assembly strategy in any synthesis may too become a vital issue.
Abstract: The remarkable diversity of techniques available for the construction of glycoproteins is presented. The complexity of synthesis is still an issue but by judicious and combined use of some of the complementary techniques, practical synthesis of complex glycoproteins will be achieved. Since glycosylation has an important role in correct protein folding, it is unlikely to be enough to "just make it", and in this regard the timing of glycosylation and assembly strategy in any synthesis may too become a vital issue.
450 citations
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TL;DR: The only common features of the varied functions of oligosaccharides are that they either mediate ‘specific recognition’ events or that they provide ‘modulation’ of biological processes.
Abstract: Many different theories have been advanced concerning the biological roles of the oligosaccharide units of individual classes of glycoconjugates. Analysis of the evidence indicates that while all of these theories are correct, exceptions to each can also be found. The biological roles of oligosaccharides appear to span the spectrum from those that are trivial, to those that are crucial for the development, growth, function or survival of an organism. Some general principles emerge. First, it is difficult to predict a priori the functions a given oligosaccharide on a given glycoconjugate might be mediating, or their relative importance to the organism. Second, the same oligosaccharide sequence may mediate different functions at different locations within the same organism, or at different times in its ontogeny or life cycle. Third, the more specific and crucial biological roles of oligosaccharides are often mediated by unusual oligosaccharide sequences, unusual presentations of common terminal sequences, or by further modifications of the sugars themselves. However, such oligosaccharide sequences are also more likely to be targets for recognition by pathogenic toxins and microorganisms. As such, they are subject to more intra- and inter-species variation because of ongoing host-pathogen interactions during evolution. In the final analysis, the only common features of the varied functions of oligosaccharides are that they either mediate 'specific recognition' events or that they provide 'modulation' of biological processes. In so doing, they generate much of the functional diversity required for the development and differentiation of complex organisms, and for their interactions with other organisms in the environment.
4,897 citations
TL;DR: The structure of ASPARAGINE-LINKed OLIGOSACCI-IARIDES and transfer-Oligosaccharide Structural Requirements, and Sequence of Processing and Specificity of Processing Enzymes are presented.
Abstract: PERSPECTIVES AND SUMMARY 631 STRUCTURES OF ASPARAGINE-LINKED OLIGOSACCI-IARIDES 632 ASSEMBLY AND TRANSFER OF THE LIPID-LINKED OLIGOSACCHARIDE ...... 635 Assembly 635 Transfer-Oligosaccharide Structural Requirements 636 Transfer-Role of Peptide Acceptor 637 OLIGOSACCHARIDE P OCESSING 639 Sequence of Processing 639 Subcellular Localization of Processing Enzymes 641 Processing in Lower Organisms 643 Specificity of Processing Enzymes 644 OTHER POS’VI~RANSLATIONAL MODIFICATIONS 653 CONTROL F OLIGOSACCHARIDE PROCESSING 655
4,699 citations
2,552 citations
1,441 citations
TL;DR: A wide variety of complex oligosaccharides has now been made accessible as a result of methodological improvements in the sphere of chemical synthesis, which can be used for the study of conformations and interactions with protein-receptor molecules.
Abstract: A wide variety of complex oligosaccharides has now been made accessible as a result of methodological improvements in the sphere of chemical synthesis, which can be used for the study of conformations and interactions with protein-receptor molecules. Such work is of particular importance because the oligosaccharide chains of glycoproteins and glycolipids anchored to the plasma membrane are important in cell-cell interactions and are receptors for enzymes, hormones, proteins, and viruses; furthermore, they determine the antigen properties of cells. The methods of synthesis available for the production of selective linkages in oligosaccharides are dealt with, particular attention being paid to conversion of saccharides into oligosaccharides, which are important from the biological point of view.
885 citations