257 results match your criteria Advances In Carbohydrate Chemistry And Biochemistry[Journal]


Preface.

Authors:
David C Baker

Adv Carbohydr Chem Biochem 2020 ;78:ix-x

Knoxville, Tennessee.

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Vinyl sulfone-modified carbohydrates: Michael acceptors and 2π partners for the synthesis of functionalized sugars and enantiomerically pure carbocycles and heterocycles.

Adv Carbohydr Chem Biochem 2020 ;78:1-134

Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, West Bengal, India. Electronic address:

Increasing demands for molecules with skeletal complexity, including those of stereochemical diversity, require new synthetic strategies. Carbohydrates have been used extensively as chiral building blocks for the synthesis of various complex molecules. On the other hand, the vinyl sulfone group has been identified as a unique functional group, which acts either as a Michael acceptor or a 2π partner in cycloaddition reactions. Read More

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Preface.

Authors:
David C Baker

Adv Carbohydr Chem Biochem 2020 ;77:ix-x

Knoxville, TN, United States.

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Mucopolysaccharidosis type II (Hunter syndrome): Clinical and biochemical aspects of the disease and approaches to its diagnosis and treatment.

Adv Carbohydr Chem Biochem 2020 26;77:71-117. Epub 2019 Oct 26.

School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, QLD, Australia. Electronic address:

Mucopolysaccharidosis type II (MPS II, Hunter syndrome) is a rare X-linked lysosomal storage disease caused by mutations of the gene encoding the lysosomal enzyme iduronate-2-sulfatase (IDS), the role of which is to hydrolytically remove O-linked sulfates from the two glycosaminoglycans (GAGs) heparan sulfate (HS) and dermatan sulfate (DS). HS and DS are linear, heterogeneous polysaccharides composed of repeating disaccharide subunits of l-iduronic acid (IdoA) or d-glucuronic acid, (1→4)-linked to d-glucosamine (for HS), or (1→3)-linked to 2-acetamido-2-deoxy-d-galactose (N-acetyl-d-galactosamine) (for DS). In healthy cells, IDS cleaves the sulfo group found at the C-2 position of terminal non-reducing end IdoA residues in HS and DS. Read More

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The scientific legacy of Frieder W. Lichtenthaler.

Adv Carbohydr Chem Biochem 2020 31;77:121-149. Epub 2020 Jul 31.

Formerly of the Clemens Schöpf Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Darmstadt, Germany. Electronic address:

This article presents a selection of topics from Professor Frieder W. Lichtenthaler's scientific lifework. It describes his contributions to, and further development of, the nitromethane cyclization of dialdehydes leading to amino sugars and amino nucleosides, as well as a new coupling methodology for purine nucleosides. Read More

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Temporary ether protecting groups at the anomeric center in complex carbohydrate synthesis.

Authors:
Wei Li Biao Yu

Adv Carbohydr Chem Biochem 2020 2;77:1-69. Epub 2020 Mar 2.

State Key Laboratory of Bio-organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China. Electronic address:

The synthesis of a carbohydrate building block usually starts with introduction of a temporary protecting group at the anomeric center and ends with its selective cleavage for further transformation. Thus, the choice of the anomeric temporary protecting group must be carefully considered because it should retain intact during the whole synthetic manipulation, and it should be chemoselectively removable without affecting other functional groups at a late stage in the synthesis. Etherate groups are the most widely used temporary protecting groups at the anomeric center, generally including allyl ethers, MP (p-methoxyphenyl) ethers, benzyl ethers, PMB (p-methoxybenzyl) eithers, and silyl ethers. Read More

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Preface.

Authors:
David C Baker

Adv Carbohydr Chem Biochem 2019 ;76:ix-x

Knoxville, TN, United States.

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November 2019

Sialic Acids in Nonenveloped Virus Infections.

Adv Carbohydr Chem Biochem 2019 7;76:65-111. Epub 2018 Nov 7.

Interfaculty Institute of Biochemistry, University of Tübingen, Tübingen, Germany; Vanderbilt University School of Medicine, Nashville, TN, United States.

Sialic acid-based glycoconjugates cover the surfaces of many different cell types, defining key properties of the cell surface such as overall charge or likely interaction partners. Because of this prominence, sialic acids play prominent roles in mediating attachment and entry to viruses belonging to many different families. In this review, we first describe how interactions between viruses and sialic acid-based glycan structures can be identified and characterized using a range of techniques. Read More

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November 2019

The Biology of Gangliosides.

Authors:
Ronald L Schnaar

Adv Carbohydr Chem Biochem 2019 23;76:113-148. Epub 2018 Oct 23.

Departments of Pharmacology and Neuroscience, Johns Hopkins University School of Medicine, Baltimore, MD, United States.

Gangliosides comprise a varied family of glycosphingolipid structures bearing one or more sialic acid residues. They are found in all mammalian tissues but are most abundant in the brain, where they represent the quantitatively major class of sialoglycans. As prominent molecular determinants on cell surfaces, they function as molecular-recognition partners for diverse glycan-binding proteins ranging from bacterial toxins to endogenous cell-cell adhesion molecules. Read More

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November 2019

Sialic Acids in Neurology.

Adv Carbohydr Chem Biochem 2019 15;76:1-64. Epub 2018 Nov 15.

Bioscience and Biotechnology Center, Nagoya University, Nagoya, Japan.

Sialic acid (Sia) is involved in many biological activities and commonly occurs as a monosialyl residue at the nonreducing terminal end of glycoconjugates. The loss of activity of UDP-GlcNAc2-epimerase/ManNAc kinase, which is a key enzyme in Sia biosynthesis, is lethal to the embryo, which clearly indicates the importance of Sia in embryogenesis. Occasionally, oligo/polymeric Sia structures such as disialic acid (diSia), oligosialic acid (oligoSia), and polysialic acid (polySia) occur in glycoconjugates. Read More

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November 2019

Preface.

Authors:
David C Baker

Adv Carbohydr Chem Biochem 2018 ;75:ix-x

Knoxville, TN, USA.

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Chemical Synthesis of Glycosides of N-Acetylneuraminic Acid.

Adv Carbohydr Chem Biochem 2018 23;75:215-316. Epub 2018 Nov 23.

Department of Chemistry, Southern Illinois University-Edwardsville, Edwardsville, IL, United States.

Investigations of methodologies aimed on improving the stereoselective synthesis of sialosides and the efficient assembly of sialic acid glycoconjugates has been the mission of dedicated research groups from the late 1960s. This review presents major accomplishments in the field, with the emphasis on significant breakthroughs and influential synthetic strategies of the last decade. Read More

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Exploration of the Sialic Acid World.

Adv Carbohydr Chem Biochem 2018 28;75:1-213. Epub 2018 Nov 28.

Bijvoet Center for Biomolecular Research, Utrecht University, Utrecht, The Netherlands. Electronic address:

Sialic acids are cytoprotectors, mainly localized on the surface of cell membranes with multiple and outstanding cell biological functions. The history of their structural analysis, occurrence, and functions is fascinating and described in this review. Reports from different researchers on apparently similar substances from a variety of biological materials led to the identification of a 9-carbon monosaccharide, which in 1957 was designated "sialic acid. Read More

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Preface.

Authors:
David C Baker

Adv Carbohydr Chem Biochem 2017 ;74:ix-x

Knoxville, TN, United States.

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Application of Porous Materials to Carbohydrate Chemistry and Glycoscience.

Authors:
Keith J Stine

Adv Carbohydr Chem Biochem 2017 13;74:61-136. Epub 2017 Nov 13.

University of Missouri-St. Louis, St. Louis, MO, United States.

There is a growing interest in using a range of porous materials to meet research needs in carbohydrate chemistry and glycoscience in general. Among the applications of porous materials reviewed in this chapter, enrichment of glycans from biological samples prior to separation and analysis by mass spectrometry is a major emphasis. Porous materials offer high surface area, adjustable pore sizes, and tunable surface chemistry for interacting with glycans, by boronate affinity, hydrophilic interactions, molecular imprinting, and polar interactions. Read More

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December 2017

The Synthesis and Biological Characterization of Acetal-Free Mimics of the Tumor-Associated Carbohydrate Antigens.

Adv Carbohydr Chem Biochem 2017 20;74:137-237. Epub 2017 Nov 20.

University of Windsor, Windsor, ON, Canada.

Carcinomas express unique carbohydrates, known as tumor-associated carbohydrate antigens (TACAs), on their surface. These are potential targets for anticancer vaccines; however, to date, no such vaccine has reached the clinic. One factor that may complicate the success of this effort is the lability of the glycosidic bond. Read More

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December 2017

Hyaluronan and Hyaluronan Fragments.

Authors:
Mary K Cowman

Adv Carbohydr Chem Biochem 2017 13;74:1-59. Epub 2017 Nov 13.

Tandon School of Engineering, New York University, New York, NY, United States.

The glycosaminoglycan hyaluronan (HA) is a key component of the microenvironment surrounding cells. In healthy tissues, HA molecules have extremely high molecular mass and consequently large hydrodynamic volumes. Tethered to the cell surface by clustered receptor proteins, HA molecules crowd each other, as well as other macromolecular species. Read More

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December 2017

Preface.

Authors:
David C Baker

Adv Carbohydr Chem Biochem 2016 ;73:ix-x

The University of Tennessee, Knoxville, Tennessee, USA.

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October 2017

Endoglycosidases for the Synthesis of Polysaccharides and Glycoconjugates.

Authors:
Chao Li Lai-Xi Wang

Adv Carbohydr Chem Biochem 2016 23;73:73-116. Epub 2016 Aug 23.

University of Maryland, College Park, MD, United States.

Recent advances in glycobiology have implicated essential roles of oligosaccharides and glycoconjugates in many important biological recognition processes, including intracellular signaling, cell adhesion, cell differentiation, cancer progression, host-pathogen interactions, and immune responses. A detailed understanding of the biological functions, as well as the development of carbohydrate-based therapeutics, often requires structurally well-defined oligosaccharides and glycoconjugates, which are usually difficult to isolate in pure form from natural sources. To meet with this urgent need, chemical and chemoenzymatic synthesis has become increasingly important as the major means to provide homogeneous compounds for functional glycocomics studies and for drug/vaccine development. Read More

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Carbohydrate-Processing Enzymes of the Lysosome: Diseases Caused by Misfolded Mutants and Sugar Mimetics as Correcting Pharmacological Chaperones.

Adv Carbohydr Chem Biochem 2016 17;73:225-302. Epub 2016 Oct 17.

Glycogroup, Institute of Organic Chemistry, Graz University of Technology, Graz, Austria.

Lysosomal storage diseases are hereditary disorders caused by mutations on genes encoding for one of the more than fifty lysosomal enzymes involved in the highly ordered degradation cascades of glycans, glycoconjugates, and other complex biomolecules in the lysosome. Several of these metabolic disorders are associated with the absence or the lack of activity of carbohydrate-processing enzymes in this cell compartment. In a recently introduced therapy concept, for susceptible mutants, small substrate-related molecules (so-called pharmacological chaperones), such as reversible inhibitors of these enzymes, may serve as templates for the correct folding and transport of the respective protein mutant, thus improving its concentration and, consequently, its enzymatic activity in the lysosome. Read More

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Recent Advances Toward Robust N-Protecting Groups for Glucosamine as Required for Glycosylation Strategies.

Adv Carbohydr Chem Biochem 2016 18;73:117-224. Epub 2016 Oct 18.

Faculty of Science, Alexandria University, Alexandria, Egypt; Universität Konstanz, Konstanz, Germany.

2-Amino-2-deoxy-d-glucose (d-glucosamine) is among the most abundant monosaccharides found in natural products. This constituent, recognized for its ubiquity, is presented in most instances as its N-acetyl derivative 2-acetamido-2-deoxy-d-glucopyranose (N-acetylglucosamine, GlcNAc, NAG). It occurs as the β-linked pyranosyl group in polysaccharides and oligosaccharides, and sometimes as the monosaccharide itself, either in its native state or as a glycoconjugate. Read More

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Stevia Glycosides: Chemical and Enzymatic Modifications of Their Carbohydrate Moieties to Improve the Sweet-Tasting Quality.

Adv Carbohydr Chem Biochem 2016 29;73:1-72. Epub 2016 Aug 29.

Groningen Biomolecular Sciences and Biotechnology Institute (GBB), University of Groningen, Groningen, The Netherlands.

Stevia glycosides, extracted from the leaves of the plant Stevia rebaudiana Bertoni, display an amazing high degree of sweetness. As processed plant products, they are considered as excellent bio-alternatives for sucrose and artificial sweeteners. Being noncaloric and having beneficial properties for human health, they are the subject of an increasing number of studies for applications in food and pharmacy. Read More

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Preface.

Authors:
David C Baker

Adv Carbohydr Chem Biochem 2015 ;72:ix-xi

University of Tennessee, Knoxville, Tennessee, USA.

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Human Milk Oligosaccharides (HMOS): Structure, Function, and Enzyme-Catalyzed Synthesis.

Authors:
Xi Chen

Adv Carbohydr Chem Biochem 2015 11;72:113-90. Epub 2015 Nov 11.

Department of Chemistry, University of California, Davis, California, USA.

The important roles played by human milk oligosaccharides (HMOS), the third major component of human milk, in the health of breast-fed infants have been increasingly recognized, as the structures of more than 100 different HMOS have now been elucidated. Despite the recognition of the various functions of HMOS as prebiotics, antiadhesive antimicrobials, and immunomodulators, the roles and the applications of individual HMOS species are less clear. This is mainly due to the limited accessibility to large amounts of individual HMOS in their pure forms. Read More

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Glycosylation of Cellulases: Engineering Better Enzymes for Biofuels.

Adv Carbohydr Chem Biochem 2015 24;72:63-112. Epub 2015 Oct 24.

Department of Chemistry and Biochemistry and BioFrontiers Institute, University of Colorado, Boulder, Colorado, USA.

Cellulose in plant cell walls is the largest reservoir of renewable carbon on Earth. The saccharification of cellulose from plant biomass into soluble sugars can be achieved using fungal and bacterial cellulolytic enzymes, cellulases, and further converted into fuels and chemicals. Most fungal cellulases are both N- and O-glycosylated in their native form, yet the consequences of glycosylation on activity and structure are not fully understood. Read More

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Synthetic Approaches to L-Iduronic Acid and L-Idose: Key Building Blocks for the Preparation of Glycosaminoglycan Oligosaccharides.

Adv Carbohydr Chem Biochem 2015 24;72:21-61. Epub 2015 Oct 24.

School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Queensland, Australia.

L-Iduronic acid (IdoA) is an important monosaccharide component of glycosaminoglycans (GAGs) such as heparin, heparan sulfate and dermatan sulfate. GAGs are complex, highly sulfated polysaccharides that mediate a multitude of physiological and pathological processes via their interactions with a range of diverse proteins. The main challenge in the synthesis of GAG oligosaccharides is the efficient gram-scale preparation of IdoA building blocks since neither IdoA nor L-idose is commercially available or readily accessible from natural sources. Read More

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Carbohydrate topics, from a critical and integrating view. Preface.

Authors:
Derek Horton

Adv Carbohydr Chem Biochem 2014 ;71:xi-xiii

Washington, DC; Columbus, Ohio.

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Modulating LPS signal transduction at the LPS receptor complex with synthetic Lipid A analogues.

Adv Carbohydr Chem Biochem 2014 ;71:339-89

Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri, USA. Electronic address:

Sepsis, defined as a clinical syndrome brought about by an amplified and dysregulated inflammatory response to infections, is one of the leading causes of death worldwide. Despite persistent attempts to develop treatment strategies to manage sepsis in the clinical setting, the basic elements of treatment have not changed since the 1960s. As such, the development of effective therapies for reducing inflammatory reactions and end-organ dysfunction in critically ill patients with sepsis remains a global priority. Read More

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