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Themed collection Glycochemistry & glycobiology

31 items
Editorial

Glycochemistry and glycobiology: a web themed issue

The communications collected in this web themed issue can only serve as an appetizer to plunge into the field. Nevertheless, they cover important up-to-date questions of glycochemistry and glycobiology.

Graphical abstract: Glycochemistry and glycobiology: a web themed issue
From the themed collection: Glycochemistry & glycobiology
Highlight

Chemistry and glycobiology

Advances in the synthesis of glycans, glycoconjugates and new technology development have contributed to our understanding of the structure and function of glycans.

Graphical abstract: Chemistry and glycobiology
Communication

Site-selective modification of proteins for the synthesis of structurally defined multivalent scaffolds

A combination of genetic code engineering and bioorthogonal functionalization was employed to obtain an artificial protein scaffold for multivalent binding studies with one or four carbohydrates installed at specific residues.

Graphical abstract: Site-selective modification of proteins for the synthesis of structurally defined multivalent scaffolds
From the themed collection: Glycochemistry & glycobiology
Communication

Preparation of oligosaccharides by homogenous enzymatic synthesis and solid phase extraction

This communication describes a method for enzymatic preparation of glycans integrating the high-efficiency of homogenous phase enzymatic reaction and fast separation of solid phase technology.

Graphical abstract: Preparation of oligosaccharides by homogenous enzymatic synthesis and solid phase extraction
From the themed collection: Glycochemistry & glycobiology
Communication

Reverse orthogonal strategy for oligosaccharide synthesis

Reverse strategy based on orthogonal protecting groups allows for oligosaccharide assembly in the reverse direction to that of conventional orthogonal strategy.

Graphical abstract: Reverse orthogonal strategy for oligosaccharide synthesis
From the themed collection: Glycochemistry & glycobiology
Communication

Glycosphingolipid synthesis employing a combination of recombinant glycosyltransferases and an endoglycoceramidase glycosynthase

The combined application of endoglycoceramidase glycosynthase(s) and recombinant glycosyltransferases facilitates efficient synthesis of glycosphingolipids with varied lipid and oligosaccharide structures.

Graphical abstract: Glycosphingolipid synthesis employing a combination of recombinant glycosyltransferases and an endoglycoceramidase glycosynthase
From the themed collection: Glycochemistry & glycobiology
Communication

cis-Glyco-fused benzopyran compounds as new amyloid-β peptide ligands

A small library of glyco-fused benzopyran Aβ ligands was synthesized and their interaction was characterised by NMR spectroscopy.

Graphical abstract: cis-Glyco-fused benzopyran compounds as new amyloid-β peptide ligands
From the themed collection: Glycochemistry & glycobiology
Communication

De novo synthesis of deoxy sugarvia a Wharton rearrangement

A divergent route to various deoxysugars has been achieved. This route utilizes a palladium(0)-catalyzed glycosylation in combination with a Wharton rearrangement as part of a new post-glycosylation transformation strategy.

Graphical abstract: De novo synthesis of deoxy sugarvia a Wharton rearrangement
From the themed collection: Glycochemistry & glycobiology
Communication

Selective oxidative debenzylation of mono- and oligosaccharides in the presence of azides

Selective removal of benzylethers by selective oxidation with NaBrO3/Na2S2O4 allowed the synthesis of the heptasaccharide azide A.

Graphical abstract: Selective oxidative debenzylation of mono- and oligosaccharides in the presence of azides
From the themed collection: Glycochemistry & glycobiology
Communication

Progress toward developing a carbohydrate-conjugate vaccine against Clostridium difficile ribotype 027: synthesis of the cell-surface polysaccharide PS-I repeating unit

The first total synthesis of a cell wall pentasaccharide repeating unit from Clostridium difficile has been achieved by the linear assembly of monosaccharide building blocks.

Graphical abstract: Progress toward developing a carbohydrate-conjugate vaccine against Clostridium difficile ribotype 027: synthesis of the cell-surface polysaccharide PS-I repeating unit
From the themed collection: Glycochemistry & glycobiology
Communication

Lewis acid-catalyzed stereoselective lactonization and subsequent glycosidation of 2-C-malonyl carbohydrates

Two different Lewis acids were employed for selective transformations in carbohydrate chemistry, affording lactones and subsequently glycosides with high stereoselectivities in good yields.

Graphical abstract: Lewis acid-catalyzed stereoselective lactonization and subsequent glycosidation of 2-C-malonyl carbohydrates
From the themed collection: Glycochemistry & glycobiology
Communication

A fluoro analogue of UDP-α-D-glucuronic acid is an inhibitor of UDP-α-D-apiose/UDP-α-D-xylose synthase

UDP-2F-glucuronic acid designed as a potential mechanistic probe acts as an inhibitor of UDP-α-D-apiose/UDP-α-D-xylose synthase.

Graphical abstract: A fluoro analogue of UDP-α-d-glucuronic acid is an inhibitor of UDP-α-d-apiose/UDP-α-d-xylose synthase
From the themed collection: Glycochemistry & glycobiology
Communication

Propargyl/methyl furanosides as potential glycosyl donors

Propargyl/methyl glycosides are reported as glycosyl donors in the presence of AuBr3 and AgOTf.

Graphical abstract: Propargyl/methyl furanosides as potential glycosyl donors
From the themed collection: Glycochemistry & glycobiology
Communication

Synthesis of a MUC1-glycopeptide–BSA conjugate vaccine bearing the 3′-deoxy-3′-fluoro-Thomsen–Friedenreich antigen

A fully functional 20 amino acid MUC1-glycopeptide antigen analog comprising a fluorinated Thomsen–Friedenreich side chain was used for the construction of a first 3′-fluoro-6TF–MUC1–BSA conjugate vaccine.

Graphical abstract: Synthesis of a MUC1-glycopeptide–BSA conjugate vaccine bearing the 3′-deoxy-3′-fluoro-Thomsen–Friedenreich antigen
From the themed collection: Glycochemistry & glycobiology
Communication

Radical C-glycosylation reaction of pyranosides with the 2,3-trans carbamate group

The radical C-glycosylation of pyranosides with 2,3-trans carbamate was achieved in high α-selectivity.

Graphical abstract: Radical C-glycosylation reaction of pyranosides with the 2,3-trans carbamate group
From the themed collection: Glycochemistry & glycobiology
Communication

Synthesis of the glycan moiety of ganglioside HPG-7 with an unusual trimer of sialic acid as the inner sugar residue

The glycan moiety of ganglioside HPG-7, isolated from the sea cucumber (Holothuria pervicax), was synthesized for the first time. The characteristic substructure, a trisialic acid sequence embedded in the glycan, was deliberately constructed by utilizing suitably differentiated sialyl units.

Graphical abstract: Synthesis of the glycan moiety of ganglioside HPG-7 with an unusual trimer of sialic acid as the inner sugar residue
From the themed collection: Glycochemistry & glycobiology
Communication

Selection of a synthetic glycan oligomer from a library of DNA-templated fragments against DC-SIGN and inhibition of HIV gp120 binding to dendritic cells

A nucleic acid-encoded carbohydrate library was prepared by split and mix synthesis, combinatorially self-assembly into over 30 000 pairs and a screened against DC-SIGN.

Graphical abstract: Selection of a synthetic glycan oligomer from a library of DNA-templated fragments against DC-SIGN and inhibition of HIV gp120 binding to dendritic cells
From the themed collection: Glycochemistry & glycobiology
Communication

Photodimerisation of glycothymidines in solution and in micelles

Glycothymidines are a new class of functional glycomimetics. They feature the change of carbohydrate presentation within a supramolecular context after [2+2] photoaddition.

Graphical abstract: Photodimerisation of glycothymidines in solution and in micelles
From the themed collection: Glycochemistry & glycobiology
Communication

Targeted pH-dependent fluorescent activity-based cathepsin probes

Acidic-pH activatable cathepsin probes have been developed that are selectively internalized via binding of the synthetic mannose cluster to the mannose receptor on dendritic cells.

Graphical abstract: Targeted pH-dependent fluorescent activity-based cathepsin probes
From the themed collection: Glycochemistry & glycobiology
Communication

The effect of heteroatom substitution of sulfur for selenium in glucosidase inhibitors on intestinal α-glucosidase activities

Selenium congeners of sulfur-containing glucosidase inhibitors show differences in inhibition of maltase glucoamylase (MGAM) and sucrase isomaltase (SI).

Graphical abstract: The effect of heteroatom substitution of sulfur for selenium in glucosidase inhibitors on intestinal α-glucosidase activities
From the themed collection: Glycochemistry & glycobiology
Communication

Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics

Diglycosylated phenols, indoles, isoindolinones, and 1,2,3-triazoles can be prepared by direct glycosylation, cyclization or cycloaddition of suitable precursors.

Graphical abstract: Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics
From the themed collection: Glycochemistry & glycobiology
Communication

Cavitand supported tetraphosphine: cyclodextrin offers a useful platform for Suzuki-Miyaura cross-coupling

A cyclodextrin-based tetraphosphine glycocatalyst induces up to 340 000 000 000 TONs and 1 000 000 000 h−1 TOFs in Suzuki-Miyaura couplings.

Graphical abstract: Cavitand supported tetraphosphine: cyclodextrin offers a useful platform for Suzuki-Miyaura cross-coupling
From the themed collection: Glycochemistry & glycobiology
Communication

Sortase A-catalyzed peptide cyclization for the synthesis of macrocyclic peptides and glycopeptides

Sortase A was discovered to mediate peptide and glycopeptide cyclization to form 15-amino acid and larger cyclic peptides and glycopeptides.

Graphical abstract: Sortase A-catalyzed peptide cyclization for the synthesis of macrocyclic peptides and glycopeptides
From the themed collection: Glycochemistry & glycobiology
Communication

Multiplexed binding determination of seven glycoconjugates for Pseudomonas aeruginosa Lectin I (PA-IL) using a DNA-based carbohydrate microarray

Seven different DNA-tag glycomimetics are mixed with PA-IL and addressed on a DNA-microarray for affinity determination.

Graphical abstract: Multiplexed binding determination of seven glycoconjugates for Pseudomonas aeruginosa Lectin I (PA-IL) using a DNA-based carbohydrate microarray
From the themed collection: Glycochemistry & glycobiology
Communication

New insight on 2-naphthylmethyl (NAP) ether as a protecting group in carbohydrate synthesis: a divergent approach towards a high-mannose type oligosaccharide library

Selective cleavage of NAP ether utilizing HF/pyridine in toluene was revealed and strategically applied towards high-mannose type oligosaccharide library synthesis.

Graphical abstract: New insight on 2-naphthylmethyl (NAP) ether as a protecting group in carbohydrate synthesis: a divergent approach towards a high-mannose type oligosaccharide library
From the themed collection: Glycochemistry & glycobiology
Communication

Automated solid phase synthesis of teichoic acids

The first automated solid phase synthesis of glycerol teichoic acids (GTAs) is reported.

Graphical abstract: Automated solid phase synthesis of teichoic acids
From the themed collection: Glycochemistry & glycobiology
Communication

Efficient chemoenzymatic synthesis of sialyl Tn-antigens and derivatives

A truncated recombinant Photobacterium sp. JH-ISH-224 α2–6-sialyltransferase was characterized for efficient one-pot three-enzyme synthesis of diverse sialyl Tn antigens.

Graphical abstract: Efficient chemoenzymatic synthesis of sialyl Tn-antigens and derivatives
From the themed collection: Glycochemistry & glycobiology
Communication

Defining oxyanion reactivities in base-promoted glycosylations

Saccharide oxyanions obtained by base treatment could be employed in glycosylation to give oligosaccharides with high stereo- and regioselectivities.

Graphical abstract: Defining oxyanion reactivities in base-promoted glycosylations
From the themed collection: Glycochemistry & glycobiology
Communication

Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation

The first direct experimental evidence for the remote participation of a 4-O-acyl group in glycosylation is provided.

Graphical abstract: Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-d-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation
From the themed collection: Glycochemistry & glycobiology
Communication

A rigid lanthanide binding tag for NMR structural analysis of carbohydrates

The first synthesis of a carbohydrate molecule covalently bound to a rigid lanthanide binding tag is reported.

Graphical abstract: A rigid lanthanide binding tag for NMR structural analysis of carbohydrates
From the themed collection: Glycochemistry & glycobiology
Open Access Communication

Chemoenzymatic synthesis of sialooligosaccharides on arrays for studies of cell surface adhesion

Sialooligosaccharides were generated by direct enzymatic glycosylation on arrays and the resulting surfaces were suitable for the study of carbohydrate-specific cell adhesion.

Graphical abstract: Chemoenzymatic synthesis of sialooligosaccharides on arrays for studies of cell surface adhesion
From the themed collection: Glycochemistry & glycobiology
31 items

About this collection

This web-based themed issue showcases high quality papers in the field of chemical biology, specifically research that deals with glycochemistry and glycobiology. The collated, invited, and peer-reviewed ChemComm articles highlight cutting edge contributions by international leaders in the field.

The guest editors of this web themed issue are Professor Peter H. Seeberger and Dr Daniel B. Werz. They are delighted by the overwhelming response that the letter of invitation produced and they express their sincere thanks to the authors. The articles received and published cover a diverse range of contemporary topics in chemical biology, including novel methodologies for the assembly of carbohydrates and carbohydrate mimetics, to the synthesis of highly complex oligosaccharides and glycoconjugates, which can be used for biological investigations.

Articles in this web themed issue will be added to the list below as soon as possible, after they are published. Please return to this page frequently to watch this collection grow.

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