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Special Issue "Glycosides"

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A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (15 December 2010)

Special Issue Editor

Guest Editor
Dr. Nikolas Pietrzik

SYNOVO GmbH, Paul Ehrlich-Straße 15, 72074 Tübingen, Germany
Website | E-Mail
Interests: carbohydrates; glycosciences; glycoconjugates; glycosidation; glycolabeling; conformational restriction; thioglycosides; glycopeptides

Special Issue Information

Dear Colleagues,

The progress in analytical sciences during the last decades - especially in the field of NMR spectroscopy - led to a deeper understanding of Glyco-biology and -chemistry. Hence the role of sugars in natural processes had to be rewritten. Primarily they were thought to be nothing more than some storage of chemically bound energy (e.g. starch) or backing structure elements (e.g. cellulose, chitin). However, due to more precise analytical methods, it became evident, that carbohydrates also have crucial allotment in biochemical recognition steps, for example enzyme substrate interactions or cell communication. For this reason the emerging field of Glycoscience quickly became attractive for medicinal research. The main obstacle scientists face today is the difficulty of getting substantial amounts of promising but often very complex Saccharides. Isolating the desired candidates from natural materials is costly and a very demanding process. The synthetic make up of such glycosides is, in all cases a long standing procedure with an immense consumption of resources. Therefore, for the fields of Glyco-biology and -chemistry, there remain unresolved challenges which would play an important role in enhancing biochemical understanding, necessary and valuable for medicinal purpose. This special issue welcomes research articles and comprehensive reviews addressing Glycoscience, reaching from saccharide synthesis and derivatization to biochemical studies on glycosides in general.

Dr. Nikolas Pietrzik
Guest Editor

Keywords

  • life sciences
  • glycoscience
  • glyco-biology
  • glyco-chemistry
  • glycosides
  • glycopeptides
  • carbohydrates
  • oligosaccharides
  • saccharide synthesis
  • saccharide mimetica
  • glycosidation
  • carbohydrate dendrimers
  • renewable primary products
  • sugars
  • libraries
  • natural products
  • screening

Published Papers (10 papers)

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Research

Jump to: Review

Open AccessArticle Tamm-Horsfall Glycoprotein Enhances PMN Phagocytosis by Binding to Cell Surface-Expressed Lactoferrin and Cathepsin G That Activates MAP Kinase Pathway
Molecules 2011, 16(3), 2119-2134; doi:10.3390/molecules16032119
Received: 7 December 2010 / Revised: 15 February 2011 / Accepted: 28 February 2011 / Published: 3 March 2011
Cited by 10 | PDF Full-text (2235 KB)
Abstract
The molecular basis of polymorphonuclear neutrophil (PMN) phagocytosis-enhancing activity (PEA) by human purified urinary Tamm-Horsfall glyco- protein (THP) has not been elucidated. In this study, we found human THP bound to lactoferrin (LF) and cathepsin G (CG) expressed on the surface of PMN,
[...] Read more.
The molecular basis of polymorphonuclear neutrophil (PMN) phagocytosis-enhancing activity (PEA) by human purified urinary Tamm-Horsfall glyco- protein (THP) has not been elucidated. In this study, we found human THP bound to lactoferrin (LF) and cathepsin G (CG) expressed on the surface of PMN, identified by a proteomic study with MALDI-TOF- LC/LC/mass spectrometric analysis. Pre-incubation of 10% SDS-PAGE electrophoresed PMN lysates with monoclonal anti-LF or anti-CG antibody reduced the binding with THP. To elucidate the signaling pathway of THP on PMN activation, we found THP enhanced ERK1/2 phosphorylation, reduced p38 MAP kinase phosphorylation, but had no effect on DNA binding of the five NF-kB family members in PMN. To further clarify whether the carbohydrate-side chains or protein-core structure in THP molecule is responsible for THP-PEA, THP was cleaved by different degrading enzymes with carbohydrate specificity (neuraminidase and β-galactosidase), protein specificity (V8 protease and proteinase K) or glycoconjugate specificity (carboxylpeptidase Y and O-sialoglycoprotein endopeptidase). We clearly demonstrated that the intact protein-core structure in THP molecule was more important for THP-PEA than carbohydrate-side chains. Putting these results together, we conclude that THP adheres to surface-expressed LF and CG on PMN and transduces signaling via the MAP kinase pathway to enhance PMN phagocytosis. Full article
(This article belongs to the Special Issue Glycosides)
Open AccessArticle Bis-Indole Derivatives for Polysaccharide Compositional Analysis and Chiral Resolution of D-, L-Monosaccharides by Ligand Exchange Capillary Electrophoresis Using Borate-Cyclodextrin as a Chiral Selector
Molecules 2011, 16(2), 1682-1694; doi:10.3390/molecules16021682
Received: 22 December 2010 / Accepted: 16 February 2011 / Published: 17 February 2011
Cited by 12 | PDF Full-text (278 KB)
Abstract
A series of aldo-bis-indole derivatives (aldo-BINs) was prepared by aromatic C-alkylation reactions of aldoses and indole in acetic acid solution. Common monosaccharides such as glucose, mannose, galactose, fucose, xylose, rhamnose, ribose, arabinose and N-acetylglucosamine were smoothly derivatized to form the UV
[...] Read more.
A series of aldo-bis-indole derivatives (aldo-BINs) was prepared by aromatic C-alkylation reactions of aldoses and indole in acetic acid solution. Common monosaccharides such as glucose, mannose, galactose, fucose, xylose, rhamnose, ribose, arabinose and N-acetylglucosamine were smoothly derivatized to form the UV absorbing aldo-BINs. The use of a capillary electrophoretic method to separate these novel aldo-BIN derivatives was established. The capillary electrophoresis conditions were set by using borate buffer (100 mM) at high pH (pH 9.0). The limit of determination was assessed to be 25 nM. The enantioseparation of D, L-pairs of aldo-BINs based on chiral ligand-exchange capillary electrophoresis technology was also achieved by using modified hydroxypropyl-β-cyclodextrin as the chiral selector in the presence of borate buffer. This aldose labeling method was applied successfully to the compositional and configurational analysis of saccharides, exemplified by a rapid and efficient method to simultaneously analyze the composition and configuration of saccharides from the medicinal herbs Cordyceps sinensis and Dendrobium huoshanense. Full article
(This article belongs to the Special Issue Glycosides)
Open AccessArticle Polycationic Glycosides
Molecules 2011, 16(2), 1508-1518; doi:10.3390/molecules16021508
Received: 23 December 2010 / Revised: 7 February 2011 / Accepted: 10 February 2011 / Published: 11 February 2011
Cited by 10 | PDF Full-text (225 KB)
Abstract
Cationic lipids have long been known to serve as antibacterial and antifungal agents. Prior efforts with attachment of cationic lipids to carbohydrate-based surfaces have suggested the possibility that carbohydrate-attached cationic lipids might serve as antibacterial and antifungal pharmaceutical agents. Toward the understanding of
[...] Read more.
Cationic lipids have long been known to serve as antibacterial and antifungal agents. Prior efforts with attachment of cationic lipids to carbohydrate-based surfaces have suggested the possibility that carbohydrate-attached cationic lipids might serve as antibacterial and antifungal pharmaceutical agents. Toward the understanding of this possibility, we have synthesized several series of cationic lipids attached to a variety of glycosides with the intent of generating antimicrobial agents that would meet the requirement for serving as a pharmaceutical agent, specifically that the agent be effective at a very low concentration as well as being biodegradable within the organism being treated. The initial results of our approach to this goal are presented. Full article
(This article belongs to the Special Issue Glycosides)
Figures

Open AccessArticle Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides
Molecules 2011, 16(2), 1113-1128; doi:10.3390/molecules16021113
Received: 7 December 2010 / Revised: 23 December 2010 / Accepted: 13 January 2011 / Published: 26 January 2011
Cited by 8 | PDF Full-text (236 KB)
Abstract
In order to develop potential anti-fungal agents, seven glycoconjugates composed of a-L-rhamnose, 6-deoxy-a-L-talose, b-D-galactose, a-D-mannose, b-D-xylose-(1®4)-6-deoxy-a-L-talose, b-D-galactose-(1®4)-a-L-rhamnose, b-D-galactose-(1®3)-b-D-xylose-(1®4)-6-deoxy-a-L-talose as the glycone and oleanolic acid as the aglycone were synthesized in an efficient and practical way using glycosyl trichloroacetimidates as donors. The structures of
[...] Read more.
In order to develop potential anti-fungal agents, seven glycoconjugates composed of a-L-rhamnose, 6-deoxy-a-L-talose, b-D-galactose, a-D-mannose, b-D-xylose-(1®4)-6-deoxy-a-L-talose, b-D-galactose-(1®4)-a-L-rhamnose, b-D-galactose-(1®3)-b-D-xylose-(1®4)-6-deoxy-a-L-talose as the glycone and oleanolic acid as the aglycone were synthesized in an efficient and practical way using glycosyl trichloroacetimidates as donors. The structures of the new compounds were confirmed by MS, 1H-NMR and 13C- NMR. Preliminary studies based on means of mycelium growth rate, indicated that all the compounds possess certain fungicidal activity against Sclerotinia sclerotiorum (Lib.) de Bary, Rhizoctonia solani Kuhn, Botrytis cinerea Pers and Phytophthora parasitica Dast. Full article
(This article belongs to the Special Issue Glycosides)
Open AccessArticle Convenient Synthesis of 3,4-Dichloro-5-hydroxy-2(5H)-Furanone Glycoconjugates
Molecules 2011, 16(2), 1011-1020; doi:10.3390/molecules16021011
Received: 14 December 2010 / Revised: 8 January 2011 / Accepted: 21 January 2011 / Published: 25 January 2011
Cited by 2 | PDF Full-text (138 KB)
Abstract
3,4-Dichloro-5-hydroxy-2(5H)-furanone treated with methyl chloroformate in the presence of diisopropylethylamine (Hünig’s base) gave the corresponding carbonate. The labile methoxycarbonyloxy group smoothly undergoes substitution by amino alcohols. The obtained 5-(w-hydroxyalkylamino) mucochloric acid derivatives reacted with peracetylated glucals using triphenylphosphine hydrobromide as a
[...] Read more.
3,4-Dichloro-5-hydroxy-2(5H)-furanone treated with methyl chloroformate in the presence of diisopropylethylamine (Hünig’s base) gave the corresponding carbonate. The labile methoxycarbonyloxy group smoothly undergoes substitution by amino alcohols. The obtained 5-(w-hydroxyalkylamino) mucochloric acid derivatives reacted with peracetylated glucals using triphenylphosphine hydrobromide as a catalyst to give the title muchloric acid glycoconjugates. Full article
(This article belongs to the Special Issue Glycosides)
Open AccessArticle Monosaccharide-NAIM Derivatives for D-, L-Configurational Analysis
Molecules 2011, 16(1), 652-664; doi:10.3390/molecules16010652
Received: 15 December 2010 / Revised: 28 December 2010 / Accepted: 13 January 2011 / Published: 17 January 2011
Cited by 8 | PDF Full-text (459 KB)
Abstract
The D-, L-enantiomeric pairs of common monosaccharides (xylose, ribose, rhamnose, arabinose, fucose, glucose, mannose, galactose, N-acetylgalactosamine, glucuronic acid and galacturonic acid) were derivatized with 2,3-naphthalenediamine to form the corresponding D-, L-aldo-NAIM derivatives. A simple and facile capillary electrophoretic method was established for
[...] Read more.
The D-, L-enantiomeric pairs of common monosaccharides (xylose, ribose, rhamnose, arabinose, fucose, glucose, mannose, galactose, N-acetylgalactosamine, glucuronic acid and galacturonic acid) were derivatized with 2,3-naphthalenediamine to form the corresponding D-, L-aldo-NAIM derivatives. A simple and facile capillary electrophoretic method was established for sugar composition analysis by simultaneously determining the migration times of these aldo-NAIMs using borate buffer at high pH (100 mM, pH 9.0). The methodology is also applicable to sialic acid (ketose monosaccharides). The quantitation level of the proposed method was in the 10~500 ppm range and the LOD was 1 ppm. The enantioseparation of D, L pairs of aldo-NAIMs were also achieved by using modified sulfated-a-cyclodextrin as the chiral selector in phosphate buffer (300 mM, pH 3.0). In addition, the combination by reductive amination of amino-aldo-NAIM agent and D-, L-enantiomeric pairs of monosaccharides formed a diastereomeric pair for saccharide configuration analysis. Aldo-NAIM derivatives are thus shown to be rapid and efficient agents for analyzing saccharide compositions and configurations with good linearity and short analysis times via capillary electrophoresis. Full article
(This article belongs to the Special Issue Glycosides)
Open AccessArticle A Quantified Ginseng (Panax ginseng C.A. Meyer) Extract Influences Lipid Acquisition and Increases Adiponectin Expression in 3T3-L1 Cells
Molecules 2011, 16(1), 477-492; doi:10.3390/molecules16010477
Received: 8 November 2010 / Revised: 21 December 2010 / Accepted: 7 January 2011 / Published: 10 January 2011
Cited by 12 | PDF Full-text (606 KB)
Abstract
A Panax ginseng extract (PGE) with a quantified amount of ginsenosides was utilized to investigate its potential to inhibit proliferation, influence lipid acquisition and adiponectin expression in 3T3-L1 cells. Seven fingerprint ginsenosides were quantified using high performance liquid chromatography and their respective molecular
[...] Read more.
A Panax ginseng extract (PGE) with a quantified amount of ginsenosides was utilized to investigate its potential to inhibit proliferation, influence lipid acquisition and adiponectin expression in 3T3-L1 cells. Seven fingerprint ginsenosides were quantified using high performance liquid chromatography and their respective molecular weights were further confirmed via LC-ESI-MS analysis from four different extraction methods. Extraction using methanol under reflux produced significantly higher amounts of ginsenosides. The methanol extract consisted of Rg1 (47.40 ± 4.28 mg/g, dry weight of extract), Re (61.62 ± 5.10 mg/g), Rf (6.14 ± 0.28 mg/g), Rb1 (21.73 ± 1.29 mg/g), Rc (78.79 ± 4.15 mg/g), Rb2 (56.80 ± 3.79 mg/g), Rd (5.90 ± 0.41 mg/g). MTT analysis showed that PGE had a concentrationdependent cytotoxic effect on 3T3-L1 preadipocyte and the LC50 value was calculated to be 18.2 ± 5 μg/mL. Cell cycle analysis showed minimal changes in all four phases. Differentiating adipocytes treated with ginseng extract had a visible decrease in lipid droplets formation measured by Oil red O staining. Consequently, triglycerides levels in media significantly (P < 0.05) decreased by 39.5% and 46.1% when treated at concentrations of 1 μg/mL and 10 μg/mL compared to untreated control cells. Western blot analysis showed that the adiponectin protein expression was significantly (P < 0.05) increased at 10 μg/mL, but not at 1 μg/mL. A quantified PGE reduced the growth of 3T3-L1 cells, down-regulated lipid accumulation and up-regulated adiponectin expression in the 3T3-L1 adipocyte cell model. Full article
(This article belongs to the Special Issue Glycosides)

Review

Jump to: Research

Open AccessReview Synthesis of Glycosides of Glucuronic, Galacturonic and Mannuronic Acids: An Overview
Molecules 2011, 16(5), 3933-3968; doi:10.3390/molecules16053933
Received: 24 March 2011 / Revised: 18 April 2011 / Accepted: 20 April 2011 / Published: 10 May 2011
Cited by 21 | PDF Full-text (472 KB)
Abstract
Uronic acids are carbohydrates present in relevant biologically active compounds. Most of the latter are glycosides or oligosaccharides linked by their anomeric carbon, so their synthesis requires glycoside-bond formation. The activation of this anomeric center remains difficult due to the presence of the
[...] Read more.
Uronic acids are carbohydrates present in relevant biologically active compounds. Most of the latter are glycosides or oligosaccharides linked by their anomeric carbon, so their synthesis requires glycoside-bond formation. The activation of this anomeric center remains difficult due to the presence of the electron-withdrawing C-5 carboxylic group. Herein we present an overview of glucuronidation, mannuronidation and galacturonidation reactions, including syntheses of prodrugs, oligosaccharides and stereochemical aspects. Full article
(This article belongs to the Special Issue Glycosides)
Open AccessReview Glycosides, Depression and Suicidal Behaviour: The Role of Glycoside-Linked Proteins
Molecules 2011, 16(3), 2688-2713; doi:10.3390/molecules16032688
Received: 17 December 2010 / Revised: 17 March 2011 / Accepted: 18 March 2011 / Published: 23 March 2011
Cited by 4 | PDF Full-text (487 KB)
Abstract
Nowadays depression and suicide are two of the most important worldwide public health problems. Although their specific molecular mechanisms are still largely unknown, glycosides can play a fundamental role in their pathogenesis. These molecules act presumably through the up-regulation of plasticity-related proteins: probably
[...] Read more.
Nowadays depression and suicide are two of the most important worldwide public health problems. Although their specific molecular mechanisms are still largely unknown, glycosides can play a fundamental role in their pathogenesis. These molecules act presumably through the up-regulation of plasticity-related proteins: probably they can have a presynaptic facilitatory effect, through the activation of several intracellular signaling pathways that include molecules like protein kinase A, Rap-1, cAMP, cADPR and G proteins. These proteins take part in a myriad of brain functions such as cell survival and synaptic plasticity. In depressed suicide victims, it has been found that their activity is strongly decreased, primarily in hippocampus and prefrontal cortex. These studies suggest that glycosides can regulate neuroprotection through Rap-1 and other molecules, and may play a crucial role in the pathophysiology of depression and suicide. Full article
(This article belongs to the Special Issue Glycosides)
Open AccessReview Chemical Arsenal for the Study of O-GlcNAc
Molecules 2011, 16(3), 1987-2022; doi:10.3390/molecules16031987
Received: 27 December 2010 / Revised: 3 February 2011 / Accepted: 15 February 2011 / Published: 28 February 2011
Cited by 13 | PDF Full-text (897 KB)
Abstract
The concepts of both protein glycosylation and cellular signaling have been influenced by O-linked-β-N-acetylglucosamine (O-GlcNAc) modification (O-GlcNAcylation) on the hydroxyl group of serine or threonine residues. Unlike conventional protein glycosylation, O-GlcNAcylation is localized in the nucleocytoplasm and
[...] Read more.
The concepts of both protein glycosylation and cellular signaling have been influenced by O-linked-β-N-acetylglucosamine (O-GlcNAc) modification (O-GlcNAcylation) on the hydroxyl group of serine or threonine residues. Unlike conventional protein glycosylation, O-GlcNAcylation is localized in the nucleocytoplasm and its cycling is a dynamic process that operates in a highly regulated manner in response to various cellular stimuli. These characteristics render O-GlcNAcylation similar to phosphorylation, which has long been considered a major regulatory mechanism in cellular processes. Various efficient chemical approaches and novel mass spectrometric (MS) techniques have uncovered numerous O-GlcNAcylated proteins that are involved in the regulation of many important cellular events. These discoveries imply that O-GlcNAcylation is another major regulator of cellular signaling. However, in contrast to phosphorylation, which is regulated by hundreds of kinases and phosphatases, dynamic O-GlcNAc cycling is catalyzed by only two enzymes: uridine diphospho-N-acetyl-glucosamine:polypeptide β-N-acetylglucosaminyl transferase (OGT) and β-D-N-acetylglucosaminidase (OGA). Many useful chemical tools have recently been used to greatly expand our understanding of the extensive crosstalk between O-GlcNAcylation and phosphorylation and hence of cellular signaling. This review article describes the various useful chemical tools that have been developed and discusses the considerable advances made in the O-GlcNAc field. Full article
(This article belongs to the Special Issue Glycosides)

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