Jump to main content
Jump to site search

Themed collection Glycosylation: New methodologies and applications

39 items
Editorial

Introduction to Glycosylation: new methodologies and applications

M. Carmen Galan, Sabine Flitsch and Antony Fairbanks introduce the Organic & Biomolecular Chemistry themed collection on glycosylation: new methodologies and applications.

Graphical abstract: Introduction to Glycosylation: new methodologies and applications
Review Article

Transition metal catalyzed glycosylation reactions – an overview

An overview of transition metal catalyzed glycosylation reactions is presented and the main trends in reactivity are discussed.

Graphical abstract: Transition metal catalyzed glycosylation reactions – an overview
From the themed collection: Catalysis & biocatalysis in OBC
Review Article

Enzymatic glycosylation involving fluorinated carbohydrates

This contribution reviews the enzymatic synthesis, including optimisation efforts, of fluorinated carbohydrates involving fluorinated donors and/or acceptors, as well as the enzymatic activation of the fluorinated donors.

Graphical abstract: Enzymatic glycosylation involving fluorinated carbohydrates
From the themed collection: Chemical biology in OBC
Review Article

Recent advances in β-L-rhamnosylation

This review describes various methodologies for the stereoselective 1,2-cis glycosylation of L-rhamnose leading to β-L-rhamnosides and their applications in oligosaccharide synthesis.

Graphical abstract: Recent advances in β-l-rhamnosylation
From the themed collection: Chemical biology in OBC
Communication

Synthesis and evaluation of sensitive coumarin-based fluorogenic substrates for discovery of α-N-acetyl galactosaminidases through droplet-based screening

Synthesis of sensitive coumarin α-GalNAc glycosides as substrates for droplet-based screening of GalNAcases.

Graphical abstract: Synthesis and evaluation of sensitive coumarin-based fluorogenic substrates for discovery of α-N-acetyl galactosaminidases through droplet-based screening
From the themed collection: Chemical biology in OBC
Communication

Chemoselective activation of ethyl vs. phenyl thioglycosides: one-pot synthesis of oligosaccharides

Ethyl thioglycosides could be selectively activated in the presence of phenyl thioglycosides carrying the same or even more armed protecting group pattern.

Graphical abstract: Chemoselective activation of ethyl vs. phenyl thioglycosides: one-pot synthesis of oligosaccharides
Communication

Thioglycoligation of aromatic thiols using a natural glucuronide donor

This is the first example of a thioglycoligase that is able to catalyse the formation of S-glucuronides using aromatic thiols and a natural glucuronide donor.

Graphical abstract: Thioglycoligation of aromatic thiols using a natural glucuronide donor
Communication

Comparison of disaccharide donors for heparan sulfate synthesis: uronic acids vs. their pyranose equivalents

Disaccharide glycosyl donors were synthesised and directly compared in glycosylations to assess their potential for heparan sulfate oligosaccharide synthesis.

Graphical abstract: Comparison of disaccharide donors for heparan sulfate synthesis: uronic acids vs. their pyranose equivalents
From the themed collection: Chemical biology in OBC
Communication

Total synthesis of tricolorin A via interrupted Pummerer reaction-mediated glycosylation and one-pot relay glycosylation

The total synthesis of tricolorin A was achieved with high efficiency based on interrupted Pummerer reaction-mediated (IPRm) glycosylation and one-pot relay glycosylation.

Graphical abstract: Total synthesis of tricolorin A via interrupted Pummerer reaction-mediated glycosylation and one-pot relay glycosylation
Communication

Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals

The use of a continuous flow platform for the rapid and highly efficient construction of differentially protected glycals from commercial sources is described.

Graphical abstract: Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals
Communication

Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination

The practical synthesis of pseudo-enantiomeric carbohydrate-based NHC–Rh complexes bearing C1 or C3 sterically differentiated positions is reported. We show that steric bulk at either C1 or C3 leads to enantiotopic discrimination in the hydrosilylation of acetophenone.

Graphical abstract: Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination
Communication

C-Glycosylation enabled by N-(glycosyloxy)acetamides

An effective C-glycosylation protocol using N-(glycosyloxy)acetamides as donors promoted by SnBr4 has been developed, delivering alkyl C-glycosides and aryl-β-C-glycosides in high yields.

Graphical abstract: C-Glycosylation enabled by N-(glycosyloxy)acetamides
From the themed collection: Synthetic methodology in OBC
Open Access Communication

Synthesis of orthogonally protected and functionalized bacillosamines

The synthesis of bacillosamines carrying different functionalities at their C-2 and C-4 amine groups is described for the first time.

Graphical abstract: Synthesis of orthogonally protected and functionalized bacillosamines
Communication

1,2-cis-Selective glucosylation enabled by halogenated benzyl protecting groups

Electron-withdrawing groups and Lewis basic solvent enable 1,2-cis-selectivity.

Graphical abstract: 1,2-cis-Selective glucosylation enabled by halogenated benzyl protecting groups
Open Access Communication

Reagent controlled stereoselective synthesis of teichoic acid α-(1,2)-glucans

Additive controlled glycosylation reactions are used for the construction of α-(1,2)-glucosidic linkages, such as those featuring in E. faecalis lipoteichoic acid.

Graphical abstract: Reagent controlled stereoselective synthesis of teichoic acid α-(1,2)-glucans
From the themed collection: Synthetic methodology in OBC
Open Access Communication

Automated access to well-defined ionic oligosaccharides

Automated Glycan Assembly grants access to ionic oligosaccharides for structural studies.

Graphical abstract: Automated access to well-defined ionic oligosaccharides
Communication

Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

Photo-induced glycosylations of several acceptors with trichloroacetimidate donors using bis(2-naphthyl)disulfide as an organo-Lewis photoacid (LPA) catalyst proceeded effectively to give the corresponding glycosides in good to high yields.

Graphical abstract: Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst
From the themed collection: Synthetic methodology in OBC
Open Access Communication

A hybrid polymer to target blood group dependence of cholera toxin

New hybrid glycopolymers were synthesized that contain two epitopes blocking GM1- and fucose-based intoxication modes of the cholera toxin.

Graphical abstract: A hybrid polymer to target blood group dependence of cholera toxin
Paper

Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution

Activation of reducing sugars in aqueous solution using DMC and triethylamine in the presence of phenols allows direct stereoselective conversion to the corresponding 1,2-trans aryl glycosides without the need for any protecting groups.

Graphical abstract: Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution
Paper

Synthesis of an STnThr analogue, structurally based on a TnThr antigen mimetic

The monosaccharide Tn and the disaccharide STn are tumor antigens with similar structures and common biosynthetic pathways.

Graphical abstract: Synthesis of an STnThr analogue, structurally based on a TnThr antigen mimetic
From the themed collection: Chemical biology in OBC
Paper

Synthesis of hyaluronic acid oligosaccharides with a GlcNAc–GlcA repeating pattern and their binding affinity with CD44

A practical route for the synthesis of hyaluronic acid oligosaccharides was developed, and a tetrasaccharide (GlcNAc–GlcA)2 was identified as the minimum length that binds to human CD44 (KD = 3.5 μM) using isothermal titration calorimetry.

Graphical abstract: Synthesis of hyaluronic acid oligosaccharides with a GlcNAc–GlcA repeating pattern and their binding affinity with CD44
Paper

Solvent-free, under air selective synthesis of α-glycosides adopting glycosyl chlorides as donors

A solvent-free, under air approach for the highly stereoselective synthesis of α-glycosides from glycosyl chloride donors, promoted by a triethylphosphite, tetrabutylammonium bromide, and N,N-diisopropylethylamine combination.

Graphical abstract: Solvent-free, under air selective synthesis of α-glycosides adopting glycosyl chlorides as donors
From the themed collection: Chemical biology in OBC
Paper

Synthesis of oligosaccharides of the linkage region of proteoglycans using regioselective glycosylation

A collection of various sulfoforms of di- and trisaccharides of the linkage region of proteoglycans were prepared using a regioselective glycosylation. Preliminary results of the impact of sulfation on CSGalNAcT-1 is also reported.

Graphical abstract: Synthesis of oligosaccharides of the linkage region of proteoglycans using regioselective glycosylation
Paper

Synthesis of type 1 Lewis b hexasaccharide antigen structures featuring flexible incorporation of L-[U-13C6]-fucose for NMR binding studies

The synthesis and use of a uniformly 13C labelled fucosyl donor as a general building block is demonstrated.

Graphical abstract: Synthesis of type 1 Lewis b hexasaccharide antigen structures featuring flexible incorporation of l-[U-13C6]-fucose for NMR binding studies
From the themed collection: Chemical biology in OBC
Open Access Paper

Asymmetric trehalose analogues to probe disaccharide processing pathways in mycobacteria

Chemoenzymatic synthesis of azido-functionalised asymmetric trehalose analogues that are resistant to enzymatic degradation to probe carbohydrate processing pathways in mycobacteria.

Graphical abstract: Asymmetric trehalose analogues to probe disaccharide processing pathways in mycobacteria
From the themed collection: Chemical biology in OBC
Paper

Sub-stoichiometric reductive etherification of carbohydrate substrates and one-pot protecting group manipulation

Polymethylhydrosiloxane (PMHS): a sub-stoichiometric reducing agent for reductive etherification of carbohydrate substrates and its application for one-pot protecting group manipulation

Graphical abstract: Sub-stoichiometric reductive etherification of carbohydrate substrates and one-pot protecting group manipulation
From the themed collection: Chemical biology in OBC
Paper

Biochemical characterisation of an α1,4 galactosyltransferase from Neisseria weaveri for the synthesis of α1,4-linked galactosides

A new α1,4 galactosyltransferase has been characterised and used for the synthesis of natural and non-natural cell surface trisaccharide antigens.

Graphical abstract: Biochemical characterisation of an α1,4 galactosyltransferase from Neisseria weaveri for the synthesis of α1,4-linked galactosides
From the themed collection: Chemical biology in OBC
Paper

Synthesis and evaluation of Nα,Nε-diacetyl-L-lysine-inositol conjugates as cancer-selective probes for metabolic engineering of GPIs and GPI-anchored proteins

This study has established a new strategy and new molecular tools for selective metabolic labeling of inositol on cancer cells, which should be useful for cancer targeting and study of GPI-anchored proteins.

Graphical abstract: Synthesis and evaluation of Nα,Nε-diacetyl-l-lysine-inositol conjugates as cancer-selective probes for metabolic engineering of GPIs and GPI-anchored proteins
From the themed collection: Chemical biology in OBC
Paper

Efficient diversification of GM3 gangliosides via late-stage sialylation and dynamic glycan structural studies with 19F solid-state NMR

GM3 gangliosides have been synthesized via late-stage α-sialylation using a macro-bicyclic sialyl donor. 19F solid-state NMR analysis of the C5-NHTFAc GM3 analog on a model membrane revealed the influence of cholesterol on glycan dynamics.

Graphical abstract: Efficient diversification of GM3 gangliosides via late-stage sialylation and dynamic glycan structural studies with 19F solid-state NMR
From the themed collection: Synthetic methodology in OBC
Paper

Synthetic preparation and immunological evaluation of β-mannosylceramide and related N-acyl analogues

The synthesis of the invariant natural killer (iNK) T cell agonist β-mannosylceramide along with a series of fatty amide analogues is reported.

Graphical abstract: Synthetic preparation and immunological evaluation of β-mannosylceramide and related N-acyl analogues
From the themed collection: Chemical biology in OBC
Paper

S-Glycosides: synthesis of S-linked arabinoxylan oligosaccharides

An S-linked disaccharide for the efficient synthesis of arabinoxylans.

Graphical abstract: S-Glycosides: synthesis of S-linked arabinoxylan oligosaccharides
From the themed collection: Chemical biology in OBC
Paper

Palladium(II)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts

An effective Pd(II)-catalyzed stereoselective C-glycosylation method has been successfully manifested for the synthesis of diversely functionalized 2,3-dideoxy C-aryl glycosides starting from glycals with a wide range of diaryliodonium salts.

Graphical abstract: Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts
From the themed collection: Synthetic methodology in OBC
Paper

β-Selective xylulofuranosylation via a conformationally-restricted glycosyl donor

Reported is the first stereoselective method for β-xylulofuranosylation, which employs 3,4-O-xylylene-protected thioglycoside donors.

Graphical abstract: β-Selective xylulofuranosylation via a conformationally-restricted glycosyl donor
From the themed collection: Chemical biology in OBC
Paper

α-Selective glycosylations using glycosyl N-(ortho-methoxyphenyl)trifluoroacetimidates

β-Selective acetimidate formation followed by α-selective catalytic activation.

Graphical abstract: α-Selective glycosylations using glycosyl N-(ortho-methoxyphenyl)trifluoroacetimidates
Paper

Chemical synthesis of human milk oligosaccharides: lacto-N-neohexaose (Galβ1 → 4GlcNAcβ1→)2 3,6Galβ1 → 4Glc

The first chemical synthesis of lacto-N-neohexaose (LNnH) has been completed using a convergent synthetic strategy.

Graphical abstract: Chemical synthesis of human milk oligosaccharides: lacto-N-neohexaose (Galβ1 → 4GlcNAcβ1→)2 3,6Galβ1 → 4Glc
From the themed collection: Chemical biology in OBC
Open Access Paper

C-2 auxiliaries for stereoselective glycosylation based on common additive functional groups

The stereoselective introduction of the glycosidic bond is one of the main challenges in chemical oligosaccharide synthesis.

Graphical abstract: C-2 auxiliaries for stereoselective glycosylation based on common additive functional groups
From the themed collection: Chemical biology in OBC
Paper

L. pneumophila CMP-5,7-di-N-acetyllegionaminic acid synthetase (LpCLS)-involved chemoenzymatic synthesis of sialosides and analogues

A bacterial CMP-5,7-di-N-acetyllegionaminic acid synthetase was characterized and used in one-pot multienzyme systems for efficient synthesis of Leg5,7Ac2-glycosides and analogs.

Graphical abstract: L. pneumophila CMP-5,7-di-N-acetyllegionaminic acid synthetase (LpCLS)-involved chemoenzymatic synthesis of sialosides and analogues
From the themed collection: Chemical biology in OBC
Paper

Exploring a glycosylation methodology for the synthesis of hydroxamate-modified alginate building blocks

Mixed sequence, C6-hydroxamate-modified alginate disaccharides are prepared using NIS/TMSOTf glycosylation.

Graphical abstract: Exploring a glycosylation methodology for the synthesis of hydroxamate-modified alginate building blocks
From the themed collection: Chemical biology in OBC
Paper

Melioidosis patient serum-reactive synthetic tetrasaccharides bearing the predominant epitopes of Burkholderia pseudomallei and Burkholderia mallei O-antigens

Tetrasaccharides mimicking Burkholderia pseudomallei and Burkholderia mallei lipopolysaccharide O-antigens were synthesized and found to be highly reactive with Thai melioidosis patient serum, highlighting their potential as vaccine candidates.

Graphical abstract: Melioidosis patient serum-reactive synthetic tetrasaccharides bearing the predominant epitopes of Burkholderia pseudomallei and Burkholderia mallei O-antigens
From the themed collection: Chemical biology in OBC
39 items

About this collection

Glycosylation: New methodologies for oligosaccharide and glycoconjugate synthesis and their applications

This themed collection, Guest Edited by Professors M. Carmen Galan, Sabine Flitsch and Antony Fairbanks, is to highlight the exciting work being carried out by carbohydrate researchers at the forefront of their field. The scope of this collection includes reactions of the anomeric centre, di- and oligosaccharide synthesis, and the development of synthetic methodology for the production of glycoconjugates for biological, biophysical or other study.

Articles in this themed collection will be added below as soon as possible after they are published.

Please return to this page frequently to see the collection grow.

Spotlight

Advertisements