Themed collection Glycochemistry & glycobiology

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.

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

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.

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

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

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

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.

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

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.

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

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

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.

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

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.

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.

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

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.

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

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

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.

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

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

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

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

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.

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

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

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

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