
Mattia GhirardelloUniversity of La Rioja | UNIRIOJA
Mattia Ghirardello
PhD
University of La Rioja, Biological Chemistry research group.
Glycochemistry.
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33
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Introduction
Publications
Publications (33)
A continuous microfluidic glycosylation strategy that requires no chromatography between steps and significantly expedites glycosylation chemistry is described. This practical approach incorporates the advantages of imidazolium-based chromatography-free purification and in situ mass spectrometry reaction monitoring to achieve fast reaction optimiza...
Glycopeptides derived from the glycoprotein mucin‐1 (MUC1) have shown potential as tumor‐associated antigens for cancer vaccine development. However, their low immunogenicity and non‐selective conjugation to carriers present significant challenges for the clinical efficacy of MUC1‐based vaccines. Here, we introduce a novel vaccine candidate based o...
Glycopeptides derived from the glycoprotein mucin‐1 (MUC1) have shown potential as tumor‐associated antigens for cancer vaccine development. However, their low immunogenicity and non‐selective conjugation to carriers present significant challenges for the clinical efficacy of MUC1‐based vaccines. Here, we introduce a novel vaccine candidate based o...
The GalNAc-transferase (GalNAc-T) family, consisting of 20 isoenzymes, regulates the O-glycosylation process of mucin glycopeptides by transferring GalNAc units to serine/threonine residues. Dysregulation of specific GalNAc-Ts is associated with various diseases, making these enzymes attractive targets for drug development. The development of inhib...
β-Mannosides are ubiquitous in nature, with diverse roles in many biological processes. Notably, Manβ1,4GlcNAc a constituent of the core N-glycan in eukaryotes was recently identified as an immune activator, highlighting its potential for use in immunotherapy. Despite their biological significance, the synthesis of β-mannosidic linkages remains one...
Soluble HMW1C-like N-glycosyltransferases (NGTs) catalyze the glycosylation of Asn residues in proteins, a process fundamental for bacterial autoaggregation, adhesion and pathogenicity. However, our understanding of their molecular mechanisms is hindered by the lack of structures of enzymatic complexes. Here, we report structures of binary and tern...
Dual-emission fluorescence probes that provide high sensitivity are key for biomedical diagnostic applications. Nontoxic carbon dots (CDs) are an emerging alternative to traditional fluorescent probes; however, robust and reproducible synthetic strategies are still needed to access materials with controlled emission profiles and improved fluorescen...
b-Mannosides are ubiquitous in nature, with diverse roles in many biological processes. Notably, Manb1,4GlcNAc a constituent of the core N-glycan in eukaryotes, was recently identified as a STING immune pathway activator, highlighting its potential for use in immunotherapy. Despite their biological significance, the synthesis of b-mannosidic linkag...
Cell surface carbohydrates mediate a wide range of carbohydrate-protein interactions key to healthy and disease mechanisms. Many of such interactions are multivalent in nature and in order to study these processes at a molecular level, many glycan-presenting platforms have been developed over the years. Among those, carbon nanoforms such as graphen...
The functionalization of glycosides with ionic compounds such as ionic liquids provides enhanced polarity for the labelled glycans thanks to the presence of a permanent positive charge. The chemical derivatisation of glycans with ionic liquids constitutes an emerging strategy to boost the detection sensitivity in MS applications. This allows the st...
The ability to modulate the cell surface structure provides a powerful tool to understand fundamental processes and also to elicit desired cellular responses. Here we report the development of a new class of 'clickable labels' to reengineer the cell surface charges of live cells. The method relies on the use of metabolic oligosaccharide engineering...
Three series of new ionic liquids (ILs), namely imidazolium‐, pyrazolium‐, and bis‐benzimidazolium‐containing ILs, were prepared from low‐cost, unprotected carbohydrates. Information on anion‐cation interactions and solvation shell were obtained via diffusion NMR and heteronuclear Overhauser correlation maps (HOESY), respectively.
The development of efficient and sensitive tools for the detection of brain cancer in patients is of the utmost importance particularly because many of these tumours go undiagnosed until the disease has advanced and when treatment is less effective. Current strategies employ antibodies (Abs) to detect Glial Fibrillary Acid Protein (GFAP) in tissue...
The development of efficient and sensitive tools for the detection of brain cancer in patients is of the utmost importance particularly because many of these tumours go undiagnosed until the disease has advanced and when treatment is less effective. Current strategies employ antibodies (Abs) to detect Glial Fibrillary Acid Protein (GFAP) in tissue...
Glioma stem-like cells (GSCs) were first described as a population which may in part be resistant to traditional chemotherapeutic therapies and responsible for tumour regrowth. Knowledge of the underlying metabolic complexity governing GSC growth and function may point to potential differences between GSCs and the tumour bulk which could be harness...
Antimicrobial resistance is a recognized global challenge. Tools for bacterial detection can combat antimicrobial resistance by facilitating evidence-based antibiotic prescribing, thus avoiding their overprescription, which contributes to the spread of resistance. Unfortunately, traditional culture-based identification methods take at least a day,...
Multivalent carbohydrate-mediated interactions are fundamental to many biological processes, including disease mechanisms. To study these significant glycan-mediated interactions at a molecular level, carbon nanoforms such as fullerenes, carbon nanotubes, or graphene and their derivatives have been identified as promising biocompatible scaffolds th...
A novel imidazolium derivative (GITag) shows superior ionisation and consequently allows increased mass spectrometric detection capabilities of oligosaccharides and N-glycans. Here we demonstrate that human serum samples can be directly...
Mucin-type O-glycosylation is among the most complex post-translational modifications. Despite mediating many physiological processes, O-glycosylation remains understudied compared to other modifications, simply because the right analytical tools are lacking. In particular, analysis of intact O-glycopeptides by mass spectrometry is challenging for...
The phosphatidyl-myo-inositol mannosyltransferase A (PimA) is an essential peripheral membrane glycosyltransferase that initiates the biosynthetic pathway of phosphatidyl-myo-inositol mannosides (PIMs), key structural elements and virulence factors of Mycobacterium tuberculosis. PimA undergoes functionally important conformational changes, includin...
Rh/Al2O3 can be used as an effective chemo-selective reductive catalyst that combines the mild conditions of catalytic hydrogenation with high selectivity for azide moieties in the presence of other hydrogenolysis labile groups such as benzyl and benzyloxycarbonyl functionalities. The practicality of this strategy is exemplified with a range of azi...
We report the design, synthesis, immunological evaluation, and conformational analysis of new saponin variants as promising vaccine adjuvants. These studies have provided expedient synthetic access to streamlined adjuvant-active saponins and yielded molecular-level insights into saponin conformation that correlated with their in vivo adjuvant activ...
Practical access to new, structurally simpler and improved saponin-based adjuvants
via shortened synthetic strategies, and the search for alternative, sustainable sources of
adjuvant-active saponins constitute an important focus in chemical immunology. Extensive structure-activity relationship studies on QS-21 have identified synthetic minimal sapo...
Representative derivatives of uridine-conjugate amino acids suitable protected for Fmoc solid-phase chemistry, have been prepared through efficient protocols using "click" reactions that include thio-ene radical reaction and copper-catalyzed azide alkyne cycloaddition (CuAAC). Several linkers between the amino acid and nucleoside units, including a...
Glycosyltransferases (GTs) are enzymes that transfer carbohydrates to a range of substrates. They play fundamental roles in recognition processes associated with several diseases. The design of glycomimetics of nucleoside diphosphate (NDP) sugars (the natural substrates) acting as inhibitors or modulators of GTs is not only necessary for the develo...
The Leloir donors are nucleotide sugars essential for a variety of glycosyltransferases (GTs) involved in the transfer of a carbohydrate to an acceptor substrate, typically a protein or an oligosaccharide. A series of less-polar nucleotide sugar analogues derived from uridine have been prepared by replacing one phosphate unit with an alkyl chain. T...
This review covers the recent advances in the synthesis of enantiomerically pure hydroxylamines employing nitrones as starting materials. Nucleophilic additions of organometallic reagents to nitrones are the most common way for introducing a hydroxyamino group into carbon skeletons with the concomitant formation of a new carbon-carbon bond. Additio...
Alkene and alkyne functional polyester-based dendrimers of generation 1 to 4 have been prepared and reacted under free-radical conditions with 2-acetamido-2-deoxy-1-thio-β-D-glucose (GlcNAc-SH). As the alkene-dendrimers underwent the addition of one thiyl radical per ene group whereas each yne group of alkyne-dendrimers was saturated by two thiyl r...
This review will describe the recent advances in the synthesis of C-nucleosides with inhibitory activity of inosine monophosphate dehydrogenase (IMPDH), a key enzyme in the biosynthesis of guanine nucleotides. The review will cover synthetic approaches of structural analogues showing modifications in the furanose ring as well as in the heterocyclic...
This review will describe the recent advances in the synthesis of C-nucleosides with inhibitory activity of inosine monophosphate dehydrogenase (IMPDH), a key enzyme in the biosynthesis of guanine nucleotides. The review will cover synthetic approaches of structural analogues showing modifications in the furanose ring as well as in the heterocyclic...