Paul Kosma
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View article: Glycosylation of an <i>N</i>‐Acetylated Glucosamine Disaccharide Using an Orthogonally Protected 3‐Iodo‐Kdo Fluoride Donor
Glycosylation of an <i>N</i>‐Acetylated Glucosamine Disaccharide Using an Orthogonally Protected 3‐Iodo‐Kdo Fluoride Donor Open
Kdo (3‐Deoxy‐ d ‐ manno ‐oct‐2‐ulosonic acid) is an essential sugar found in bacterial lipopolysaccharides with significant biomedical relevance. This study introduces an orthogonally protected 3‐iodo‐Kdo fluoride donor and demonstrates it…
View article: Potentiating Activity of GmhA Inhibitors on Gram-Negative Bacteria
Potentiating Activity of GmhA Inhibitors on Gram-Negative Bacteria Open
Inhibition of the biosynthesis of bacterial heptoses opens novel perspectives for antimicrobial therapies. The enzyme GmhA responsible for the first committed biosynthetic step catalyzes the conversion of sedoheptulose 7-phosphate into d-g…
View article: β-Elimination as major side reaction in periodate-oxidation of cellulosic model mono- and disaccharides
β-Elimination as major side reaction in periodate-oxidation of cellulosic model mono- and disaccharides Open
To structurally characterize periodate-oxidized cellulosic substrates, methyl 4- O -methyl β- d -glucopyranoside and methyl 4’- O -methyl-cellobioside were subjected to periodate treatment at pH 4.8–5.0. Oxidation of the monosaccharide usi…
View article: Site‐Specific Multi‐Functionalization of the Carrier Protein CRM<sub>197</sub> by Disulfide Rebridging for Conjugate Vaccine Development
Site‐Specific Multi‐Functionalization of the Carrier Protein CRM<sub>197</sub> by Disulfide Rebridging for Conjugate Vaccine Development Open
Conjugation of an antigen to a carrier protein is widely used for vaccine development. To develop the next generation of conjugate vaccines, we describe here a method for the controlled multi‐functionalization of the widely employed carrie…
View article: The S-layer homology domains of Paenibacillus alvei surface protein SpaA bind to cell wall polysaccharide through the terminal monosaccharide residue
The S-layer homology domains of Paenibacillus alvei surface protein SpaA bind to cell wall polysaccharide through the terminal monosaccharide residue Open
Self-assembling (glyco)protein surface layers (S-layers) are ubiquitous prokaryotic cell-surface structures involved in structural maintenance, nutrient diffusion, host adhesion, virulence, and other processes, which makes them appealing t…
View article: A Lead-Based Fragment Library Screening of the Glycosyltransferase WaaG from Escherichia coli
A Lead-Based Fragment Library Screening of the Glycosyltransferase WaaG from Escherichia coli Open
Glucosyl transferase I (WaaG) in E. coli catalyzes the transfer of an α-d-glucosyl group to the inner core of the lipopolysaccharide (LPS) and plays an important role in the biogenesis of the outer membrane. If its activity could be inhibi…
View article: Synthetic Neoglycoconjugates of Hepta‐ and Nonamannoside Ligands for Eliciting Oligomannose‐Specific HIV‐1‐Neutralizing Antibodies
Synthetic Neoglycoconjugates of Hepta‐ and Nonamannoside Ligands for Eliciting Oligomannose‐Specific HIV‐1‐Neutralizing Antibodies Open
Oligomannose‐type glycans on the spike protein of HIV‐1 constitute relevant epitopes to elicit broadly neutralizing antibodies (bnAbs). Herein we describe an improved synthesis of α‐ and β‐linked hepta‐ and nonamannosyl ligands that were s…
View article: Achieving Absolute Molar Lipid Concentrations: A Phospholipidomics Cross-Validation Study
Achieving Absolute Molar Lipid Concentrations: A Phospholipidomics Cross-Validation Study Open
Standardization is essential in lipidomics and part of a huge community effort. However, with the still ongoing lack of reference materials, benchmarking quantification is hampered. Here, we propose traceable lipid class quantification as …
View article: A Combination of Structural, Genetic, Phenotypic and Enzymatic Analyses Reveals the Importance of a Predicted Fucosyltransferase to Protein O-Glycosylation in the Bacteroidetes
A Combination of Structural, Genetic, Phenotypic and Enzymatic Analyses Reveals the Importance of a Predicted Fucosyltransferase to Protein O-Glycosylation in the Bacteroidetes Open
Diverse members of the Bacteroidetes phylum have general protein O-glycosylation systems that are essential for processes such as host colonization and pathogenesis. Here, we analyzed the function of a putative fucosyltransferase (FucT) fa…
View article: Assaying Paenibacillus alvei CsaB-Catalysed Ketalpyruvyltransfer to Saccharides by Measurement of Phosphate Release
Assaying Paenibacillus alvei CsaB-Catalysed Ketalpyruvyltransfer to Saccharides by Measurement of Phosphate Release Open
Ketalpyruvyltransferases belong to a widespread but little investigated class of enzymes, which utilise phosphoenolpyruvate (PEP) for the pyruvylation of saccharides. Pyruvylated saccharides play pivotal biological roles, ranging from prot…
View article: Potential of Inulin-Fructooligosaccharides Extract Produced from Red Onion (Allium cepa var. viviparum (Metz) Mansf.) as an Alternative Prebiotic Product
Potential of Inulin-Fructooligosaccharides Extract Produced from Red Onion (Allium cepa var. viviparum (Metz) Mansf.) as an Alternative Prebiotic Product Open
Red onion is a popular ingredient in many Thai dishes and has recently been promoted for commercial cultivation. In this study, inulin-fructooligosaccharides (inulin-FOSs) were extracted from red onions in a simplified extraction method. T…
View article: Determination of modification degree of polysialylated therapeutic proteins using 1H-NMR spectroscopy
Determination of modification degree of polysialylated therapeutic proteins using 1H-NMR spectroscopy Open
Water soluble polymers and their derivatives bound to proteins can dramatically favor the biological activity of new drugs and vaccines. Quantification of the modification degree of the protein is crucial during the development and licensi…
View article: The Structural Difference of Isobaric N-Glycans of Two Microalgae Samples Reveals Taxonomic Distance
The Structural Difference of Isobaric N-Glycans of Two Microalgae Samples Reveals Taxonomic Distance Open
Microalgae of the Chlorella clade are extensively investigated as an environmentally friendly source of renewable biofuels and high-value nutrients. In addition, essentially unprocessed Chlorella serves as wholesome food additive. A recent…
View article: Synthesis of a pyruvylated N-acetyl-β-D-mannosamine containing disaccharide repeating unit of a cell wall glycopolymer from Paenibacillus alvei
Synthesis of a pyruvylated N-acetyl-β-D-mannosamine containing disaccharide repeating unit of a cell wall glycopolymer from Paenibacillus alvei Open
A disaccharide implicated in anchoring of bacterial Surface-layer proteins to secondary cell wall glycopolymers has been prepared by glycosylation of a protected N-acetyl glucosamine acceptor with a glucopyranosyl donor to generate the β-(…
View article: Zwitterionic Phosphodiester-Substituted Neoglycoconjugates as Ligands for Antibodies and Acute Phase Proteins
Zwitterionic Phosphodiester-Substituted Neoglycoconjugates as Ligands for Antibodies and Acute Phase Proteins Open
Zwitterionic modifications of glycans, such as phosphorylcholine and phosphoethanolamine, are known from a range of prokaryotic and eukaryotic species and are recognized by mammalian antibodies and pentraxins; however, defined saccharide l…
View article: Stereoelectronic Effects Impact Glycan Recognition
Stereoelectronic Effects Impact Glycan Recognition Open
Recognition of distinct glycans is central to biology, and lectins mediate this function. Lectin glycan preferences are usually centered on specific monosaccharides. In contrast, human intelectin-1 (hItln-1, also known as Omentin-1) is a s…
View article: Stereoelectronic Effects Impact Glycan Recognition
Stereoelectronic Effects Impact Glycan Recognition Open
Recognition of distinct glycans is central to biology, and lectins mediate this function. Lectin glycan preferences are usually centered on specific monosaccharides. In contrast, human intelectin-1 (hItln-1, also known as Omentin-1) is a s…
View article: Stereoelectronic Effects Impact Glycan Recognition
Stereoelectronic Effects Impact Glycan Recognition Open
Recognition of distinct glycans is central to biology, and lectins mediate this function. Lectin glycan preferences are usually centered on specific monosaccharides. In contrast, human intelectin-1 (hItln-1, also known as Omentin-1) is a s…
View article: Synthesis of <i>C</i> -glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-ʟ-arabinose
Synthesis of <i>C</i> -glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-ʟ-arabinose Open
The incorporation of basic substituents into the structurally conserved domains of cell wall lipopolysaccharides has been identified as a major mechanism contributing to antimicrobial resistance of Gram-negative pathogenic bacteria. Inhibi…
View article: Molecular Conformations of Di-, Tri-, and Tetra-α-(2→8)-Linked Sialic Acid from NMR Spectroscopy and MD Simulations
Molecular Conformations of Di-, Tri-, and Tetra-α-(2→8)-Linked Sialic Acid from NMR Spectroscopy and MD Simulations Open
By using molecular dynamics simulations with an efficient enhanced sampling technique and in combination with nuclear magnetic resonance (NMR) spectroscopy quantitative structural information on α -2,8-linked sialic acids is presented. We …
View article: Cover Feature: Synthetic Phosphodiester‐Linked 4‐Amino‐4‐deoxy‐<scp>l</scp>‐arabinose Derivatives Demonstrate that ArnT is an Inverting Aminoarabinosyl Transferase (ChemBioChem 23/2019)
Cover Feature: Synthetic Phosphodiester‐Linked 4‐Amino‐4‐deoxy‐<span>l</span>‐arabinose Derivatives Demonstrate that ArnT is an Inverting Aminoarabinosyl Transferase (ChemBioChem 23/2019) Open
The action of a membrane-embedded lipid-to-lipid glycosyltransferase (ArnT) on a synthetic lipid-shortened phosphodiester derivative of 4-amino-4-deoxy-L-arabinose (Ara4N) forms a new phosphodiester linkage to the lipid A part of bacterial…
View article: Synthesis of C-glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-L-arabinose
Synthesis of C-glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-L-arabinose Open
Incorporation of basic substituents into the structurally conserved domains of cell-wall lipopolysaccharides has been identified as a major mechanism contributing to antimicrobial resistance of Gram-negative pathogenic bacteria. Inhibition…
View article: ADP heptose, a novel pathogen‐associated molecular pattern identified in <i>Helicobacter pylori</i>
ADP heptose, a novel pathogen‐associated molecular pattern identified in <i>Helicobacter pylori</i> Open
The gastric pathogen Helicobacter pylori activates the NF‐κB pathway in human epithelial cells via the recently discovered α‐kinase 1 TRAF‐interacting protein with forkhead‐associated domain (TIFA) axis. We and others showed that this path…
View article: Synthesis of an Undecasaccharide Featuring an Oligomannosidic Heptasaccharide and a Bacterial Kdo-lipid A Backbone for Eliciting Neutralizing Antibodies to Mammalian Oligomannose on the HIV-1 Envelope Spike
Synthesis of an Undecasaccharide Featuring an Oligomannosidic Heptasaccharide and a Bacterial Kdo-lipid A Backbone for Eliciting Neutralizing Antibodies to Mammalian Oligomannose on the HIV-1 Envelope Spike Open
Lipooligosaccharides (LOS) from the bacterium Rhizobium radiobacter Rv3 are structurally related to antigenic mammalian oligomannoses on the HIV-1 envelope glycoprotein spike that are targets for broadly neutralizing antibodies. Here, we p…
View article: 2-<i>O</i>-Benzyloxycarbonyl protected glycosyl donors: a revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation
2-<i>O</i>-Benzyloxycarbonyl protected glycosyl donors: a revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation Open
Benzyloxycarbonyl can be used as participating group for the diastereoselective glycosylation of base-labile products and the synthesis of glycosyl esters.