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.
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.
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.
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.
Reverse orthogonal strategy for
Reverse strategy based on orthogonal protecting groups allows for oligosaccharide assembly in the reverse direction to that of conventional orthogonal strategy.
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.
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.
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.
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.
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.
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.
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.
Propargyl/methyl furanosides as potential
Propargyl/methyl glycosides are reported as glycosyl donors in the presence of AuBr3 and AgOTf.
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.
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.
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.
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.
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.
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.
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).
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.
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.
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.
Multiplexed binding determination of seven glycoconjugates for Pseudomonas aeruginosa Lectin I (PA-IL) using a DNA-based
Seven different DNA-tag glycomimetics are mixed with PA-IL and addressed on a DNA-microarray for affinity determination.
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.
Automated solid phase synthesis of teichoic acids
The first automated solid phase synthesis of glycerol teichoic acids (GTAs) is reported.
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.
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.
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.
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.
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.
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.