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Advances on Glycoconjugates – Chemistry and Chemical Biology
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Advances on Glycoconjugates – Chemistry and Chemical Biology

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Chemical Biology".

Deadline for manuscript submissions: closed (31 March 2023) | Viewed by 17130

Special Issue Editors

Prof. Dr. Patrick M. Martin

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Guest Editor
Unit of Transformations & Agroressources, ULR7519, Universite d'Artois, 62408 Bethune, France
Interests: bio-based chemistry; carbohydrates; lipids; secondary metabolites; amphiphilic; drug targeting, bio-control; materials
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Sandrine Bouquillon

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Guest Editor
Institute of Molecular Chemistry of Reims, UMR CNRS 7312, Université Reims Champagne, Ardenne, 51687 Reims, France
Interests: green chemistry; sugar-based and acid-based surfactants; glyco-and glycerodendrimers; bio-based ionic liquids; synthesis; catalysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The term glycoconjugates is used to generally classify carbohydrates covalently linked to other chemical species such as proteins, peptides, lipids, and saccharides. Glycoconjugates are formed during glycosylation. Glycostructures play a highly diverse and crucial role in multiple organisms and important systems in biology, physiology, medicine, bioengineering, and technology. Glycoconjugates are very diverse in their structure and function; they are widely distributed in nature and are produced by all organisms, plants, animals, and microorganisms. Natural glycoconjugates have excellent characteristics and biocompatibility, which make them extremely attractive for many applications. The diverse nature of the aglycone portion of glycoconjugates allows various applications and offers virtually unlimited options for developing new compounds with improved properties for their targeted applications.

The Special Issue "Advances in Glycoconjugates—Chemistry and Chemical Biology" aims to provide a forum for the dissemination of the latest studies and a broad coverage of research progress and up-to-date data dealing with various fundamental and applied aspects of glycoconjugates. For this Special Issue, we are seeking contributions from researchers to discuss all aspects of glycoconjugates: extraction, characterization, formulation, chemical/enzymatic modifications involving non-conventional media or activation modes for applications in different fields. We anticipate that this Special Issue will provide a unique platform for the dissemination of new concepts and applications regarding glycoconjugates in order to continue to motivate research in the field.

Prof. Dr. Patrick M. Martin
Prof. Dr. Sandrine Bouquillon
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Extraction, Characterization, Analysis
  • Glycolipids
  • Glycopeptides
  • Glycoproteins
  • Oligosaccharides
  • Chemo-enzymatic modification/synthesis/green synthesis
  • Glycosylation
  • Glycodendrimers
  • Glycomimetics
  • Glycosyltransferases
  • Amphiphiles
  • Bio-control
  • Food applications
  • Cosmetic applications
  • Biological applications
  • Biomedical applications; Biomaterials, drug-targeting systems
  • Remediation

Published Papers (6 papers)

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Research

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32 pages, 8968 KiB  
Article
L-Rhamnose and Phenolic Esters-Based Monocatenar and Bolaform Amphiphiles: Eco-Compatible Synthesis and Determination of Their Antioxidant, Eliciting and Cytotoxic Properties
by Emad Kordkatooli, Katia Bacha, Sandra Villaume, Stephan Dorey, Jean-Claude Monboisse, Sylvie Brassart-Pasco, Jean-Pierre Mbakidi and Sandrine Bouquillon
Molecules 2023, 28(13), 5154; https://doi.org/10.3390/molecules28135154 - 30 Jun 2023
Viewed by 745
Abstract
Symmetrical and dissymmetrical bolaforms were prepared with good to high yields from unsaturated L-rhamnosides and phenolic esters (ferulic, phloretic, coumaric, sinapic and caffeic) using two eco-compatible synthetic strategies involving glycosylation, enzymatic synthesis and cross-metathesis under microwave activation. The plant-eliciting activity of these new [...] Read more.
Symmetrical and dissymmetrical bolaforms were prepared with good to high yields from unsaturated L-rhamnosides and phenolic esters (ferulic, phloretic, coumaric, sinapic and caffeic) using two eco-compatible synthetic strategies involving glycosylation, enzymatic synthesis and cross-metathesis under microwave activation. The plant-eliciting activity of these new compounds was investigated in Arabidopsis model plants. We found that the monocatenar rhamnosides and bolaforms activate the plant immune system with a response depending on the carbon chain length and the nature of the hydrophilic heads. Their respective antioxidant activities were also evaluated, as well as their cytotoxic properties on dermal cells for cosmetic uses. We showed that phenolic ester-based compounds present good antioxidant activities and that their cytotoxicity is low. These properties are also dependent on the carbon chains used. Full article
(This article belongs to the Special Issue Advances on Glycoconjugates – Chemistry and Chemical Biology)
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12 pages, 3432 KiB  
Article
Synthetic Studies on the Incorporation of N-Acetylallosamine in Hyaluronic Acid-Inspired Thiodisaccharides
by Alejandro E. Cristófalo and María Laura Uhrig
Molecules 2021, 26(1), 180; https://doi.org/10.3390/molecules26010180 - 01 Jan 2021
Cited by 1 | Viewed by 1854
Abstract
Two approaches for the synthesis of the thiodisaccharide β-S-GlcA(1→3)β-S-AllNAc are described here. The target disaccharide was a C-3 epimer and thio-analogue of the hyaluronic acid repetitive unit, tuned with a thiopropargyl anomeric group for further click conjugation. Thus, we analysed and tested two [...] Read more.
Two approaches for the synthesis of the thiodisaccharide β-S-GlcA(1→3)β-S-AllNAc are described here. The target disaccharide was a C-3 epimer and thio-analogue of the hyaluronic acid repetitive unit, tuned with a thiopropargyl anomeric group for further click conjugation. Thus, we analysed and tested two convenient sequences, combining the two key steps required to introduce the thioglycosidic bonds and consequently reach the target molecule: the SN2 substitution of a good leaving group (triflate) present at C-3 of a GlcNAc derivative and the introduction of the anomeric thiopropargyl substituent. The use of a 2-azido precursor showed to be a convenient substrate for the SN2 step. Nevertheless, further protecting group manipulation and the introduction of the thiopropargyl anomeric residue were then required. This approach showed to provide access to a variety of thiodisaccharide derivatives as interesting building blocks for the construction of neoglycoconjugates. Full article
(This article belongs to the Special Issue Advances on Glycoconjugates – Chemistry and Chemical Biology)
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20 pages, 4382 KiB  
Article
Importance of the C12 Carbon Chain in the Biological Activity of Rhamnolipids Conferring Protection in Wheat against Zymoseptoria tritici
by Rémi Platel, Ludovic Chaveriat, Sarah Le Guenic, Rutger Pipeleers, Maryline Magnin-Robert, Béatrice Randoux, Pauline Trapet, Vincent Lequart, Nicolas Joly, Patrice Halama, Patrick Martin, Monica Höfte, Philippe Reignault and Ali Siah
Molecules 2021, 26(1), 40; https://doi.org/10.3390/molecules26010040 - 23 Dec 2020
Cited by 14 | Viewed by 3397
Abstract
The hemibiotrophic fungus Zymoseptoria tritici, responsible for Septoria tritici blotch, is currently the most devastating foliar disease on wheat crops worldwide. Here, we explored, for the first time, the ability of rhamnolipids (RLs) to control this pathogen, using a total of 19 [...] Read more.
The hemibiotrophic fungus Zymoseptoria tritici, responsible for Septoria tritici blotch, is currently the most devastating foliar disease on wheat crops worldwide. Here, we explored, for the first time, the ability of rhamnolipids (RLs) to control this pathogen, using a total of 19 RLs, including a natural RL mixture produced by Pseudomonas aeruginosa and 18 bioinspired RLs synthesized using green chemistry, as well as two related compounds (lauric acid and dodecanol). These compounds were assessed for in vitro antifungal effect, in planta defence elicitation (peroxidase and catalase enzyme activities), and protection efficacy on the wheat-Z. tritici pathosystem. Interestingly, a structure-activity relationship analysis revealed that synthetic RLs with a 12 carbon fatty acid tail were the most effective for all examined biological activities. This highlights the importance of the C12 chain in the bioactivity of RLs, likely by acting on the plasma membranes of both wheat and Z. tritici cells. The efficacy of the most active compound Rh-Est-C12 was 20-fold lower in planta than in vitro; an optimization of the formulation is thus required to increase its effectiveness. No Z. tritici strain-dependent activity was scored for Rh-Est-C12 that exhibited similar antifungal activity levels towards strains differing in their resistance patterns to demethylation inhibitor fungicides, including multi-drug resistance strains. This study reports new insights into the use of bio-inspired RLs to control Z. tritici. Full article
(This article belongs to the Special Issue Advances on Glycoconjugates – Chemistry and Chemical Biology)
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13 pages, 8261 KiB  
Article
Comparison of Different HILIC Stationary Phases in the Separation of Hemopexin and Immunoglobulin G Glycopeptides and Their Isomers
by Katarina Molnarova and Petr Kozlík
Molecules 2020, 25(20), 4655; https://doi.org/10.3390/molecules25204655 - 13 Oct 2020
Cited by 24 | Viewed by 3644
Abstract
Protein glycosylation analysis is challenging due to the structural variety of complex conjugates. However, chromatographically separating glycans attached to tryptic peptides enables their site-specific characterization. For this purpose, we have shown the importance of selecting a suitable hydrophilic interaction liquid chromatography (HILIC) stationary [...] Read more.
Protein glycosylation analysis is challenging due to the structural variety of complex conjugates. However, chromatographically separating glycans attached to tryptic peptides enables their site-specific characterization. For this purpose, we have shown the importance of selecting a suitable hydrophilic interaction liquid chromatography (HILIC) stationary phase in the separation of glycopeptides and their isomers. Three different HILIC stationary phases, i.e., HALO® penta-HILIC, Glycan ethylene bridged hybrid (BEH) Amide, and ZIC-HILIC, were compared in the separation of complex N-glycopeptides of hemopexin and Immunoglobulin G glycoproteins. The retention time increased with the polarity of the glycans attached to the same peptide backbone in all HILIC columns tested in this study, except for the ZIC-HILIC column when adding sialic acid to the glycan moiety, which caused electrostatic repulsion with the negatively charged sulfobetaine functional group, thereby decreasing retention. The HALO® penta-HILIC column provided the best separation results, and the ZIC-HILIC column the worst. Moreover, we showed the potential of these HILIC columns for the isomeric separation of fucosylated and sialylated glycoforms. Therefore, HILIC is a useful tool for the comprehensive characterization of glycoproteins and their isomers. Full article
(This article belongs to the Special Issue Advances on Glycoconjugates – Chemistry and Chemical Biology)
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Review

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22 pages, 10277 KiB  
Review
Azo-Dyes-Grafted Oligosaccharides—From Synthesis to Applications
by Estelle Léonard and Antoine Fayeulle
Molecules 2021, 26(11), 3063; https://doi.org/10.3390/molecules26113063 - 21 May 2021
Cited by 7 | Viewed by 3437
Abstract
Azobenzenes are photochromic molecules that possess a large range of applications. Their syntheses are usually simple and fast, and their purifications can be easy to perform. Oligosaccharide is also a wide family of biopolymer constituted of linear chain of saccharides. It can be [...] Read more.
Azobenzenes are photochromic molecules that possess a large range of applications. Their syntheses are usually simple and fast, and their purifications can be easy to perform. Oligosaccharide is also a wide family of biopolymer constituted of linear chain of saccharides. It can be extracted from biomass, as for cellulose, being the principal constituent of plant cell wall, or it can be enzymatically produced as for cyclodextrins, having properties not far from cellulose. Combining these two materials families can afford interesting applications such as controlled drug-release systems, photochromic liquid crystals, photoresponsive films or even fluorescent indicators. This review will compile the different syntheses of azo-dyes-grafted oligosaccharides, and will show their various applications. Full article
(This article belongs to the Special Issue Advances on Glycoconjugates – Chemistry and Chemical Biology)
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20 pages, 5267 KiB  
Review
Overview of the Assays to Probe O-Linked β-N-Acetylglucosamine Transferase Binding and Activity
by Cyril Balsollier, Roland J. Pieters and Marko Anderluh
Molecules 2021, 26(4), 1037; https://doi.org/10.3390/molecules26041037 - 16 Feb 2021
Cited by 4 | Viewed by 3246
Abstract
O-GlcNAcylation is a posttranslational modification that occurs at serine and threonine residues of protein substrates by the addition of O-linked β-d-N-acetylglucosamine (GlcNAc) moiety. Two enzymes are involved in this modification: O-GlcNac transferase (OGT), which attaches the [...] Read more.
O-GlcNAcylation is a posttranslational modification that occurs at serine and threonine residues of protein substrates by the addition of O-linked β-d-N-acetylglucosamine (GlcNAc) moiety. Two enzymes are involved in this modification: O-GlcNac transferase (OGT), which attaches the GlcNAc residue to the protein substrate, and O-GlcNAcase (OGA), which removes it. This biological balance is important for many biological processes, such as protein expression, cell apoptosis, and regulation of enzyme activity. The extent of this modification has sparked interest in the medical community to explore OGA and OGT as therapeutic targets, particularly in degenerative diseases. While some OGA inhibitors are already in phase 1 clinical trials for the treatment of Alzheimer’s disease, OGT inhibitors still have a long way to go. Due to complex expression and instability, the discovery of potent OGT inhibitors is challenging. Over the years, the field has grappled with this problem, and scientists have developed a number of techniques and assays. In this review, we aim to highlight assays and techniques for OGT inhibitor discovery, evaluate their strength for the field, and give us direction for future bioassay methods. Full article
(This article belongs to the Special Issue Advances on Glycoconjugates – Chemistry and Chemical Biology)
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