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Special Issue "Conjugate Vaccines from Carbohydrate Antigens"

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

Deadline for manuscript submissions: 31 May 2018

Special Issue Editors

Guest Editor
Dr. Paul Kovac

NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA
Website | E-Mail
Phone: 301-496-3569
Interests: organic chemistry; carbohydrate chemistry; synthetic oligosaccharides; development of conjugate vaccines from synthetic and bacterial carbohydrate antigens
Guest Editor
Dr. Peng Xu

NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA
Website | E-Mail
Interests: neoglycoconjugate vaccine; conjugation chemistry; chemical glycosylation; oligosaccharide synthesis; lipopolysaccharide; O-specific polysaccharide
Guest Editor
Dr. Helene Pfister

NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA
Website | E-Mail
Interests: carbohydrate chemistry; oligosaccharides synthesis; conjugation chemistry; glycoproteins; glycopolymers; glycoconjugate vaccines

Special Issue Information

Dear Colleagues,

Vaccines are one of the most cost-effective way to control infectious diseases. In addition to protein antigens, cell surface carbohydrates are widely used as antigenic components of vaccines. Since the preparation and clinical use of the first carbohydrate–protein conjugate vaccine in the 1980s, the advantages of this class of vaccines, such as longer shelf life and protective immunity, fewer undesirable side-effects, and better protection in children, have been largely recognized. Glycoconjugate vaccines are composed of carbohydrate antigens, covalently linked to a carrier moiety, usually a non-toxic protein. The carbohydrate moiety is normally an oligosaccharide or polysaccharide of bacterial origins. However, several glycoconjugate vaccines from synthetic oligosaccharides are in development. While immunogenic proteins, such as tetanus toxoid are generally used as carriers of antigens, recent advances in the field showed the potential of immunogenic peptides for the same purpose.

This Special Issue is dedicated to the design, synthesis, and antigenicity/immunogenicity studies of glycoconjugate vaccines. In addition, we welcome contributions on conjugation methodology, synthesis of conjugation-ready oligosaccharides related to protective antigens, and purification and characterization of bacterial polysaccharides.

Dr. Paul Kovac
Dr. Peng Xu
Dr. Helene Pfister
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 papers will be 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 monthly 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 1800 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.


  • glycoconjugates
  • neoglycoconjugate
  • conjugation methodology
  • immunogens
  • carbohydrate antigens
  • bacterial carbohydrates
  • vaccines

Published Papers

This special issue is now open for submission, see below for planned papers.

Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: Mechanism of Immune Response to Conjugated Polysaccharide Vaccines, Current State of Knowledge and Future Perspectives
Authors: A.V. Kozyr * and A.V. Kolesnikov
Affiliation: State Research Center for Applied Microbiology and Biotechnology Obolensk, Moscow oblast, Russia
Email: avkozyr@gmail.com
Abstract: Polysaccharide bacterial antigens are widely used to preparation of vaccines protecting humans from infectious diseases. It has been long recognized that chemical conjugation of bacterial polysaccharide antigens with carrier proteins enhances protection by activating T-cell immunity and inducing secondary immune response and long-lasting immune memory. However, for many years, the mechanism of activation of glycan-specific immune response by carrier proteins remained to be poorly understood. Recent studies provided new information on how conjugation to a carrier protein can aid to T-cell recognition of carbohydrate antigens. Progress in understanding the mechanisms of immune recognition of glycoconjugate vaccines opens new opportunities rational design of conjugated vaccines and synthesis of glycoconjugates with increased effectiveness of protective action.

Title: A Three Component Synthetic Vaccine Containing a β-Mannan T-Cell Peptide Epitope and a Dendritic Cell Ligand
Author: David R. Bundle
Affiliation: Department of Chemistry, Gunning/Lemieux Chemistry Centre, 11227 Saskatchewan Drive, University of Alberta, Edmonton, Alberta T6G 2G2, Canada
Email: dave.bundle@ualberta.ca
Abstract: A fully synthetic conjugate vaccine was constructed from a 1,2-linked β-mannose trisaccharide conjugated to a T-cell peptide which has previously been shown to afford protection against Candida albicans. This combined B and T cell epitope was synthesized with a C-terminal azidolysine residue for subsequent conjugation by click chemistry. Four copies of a β-1,3 linked hexaglucan dendritic cell epitope were conjugated to an asymmetric dendrimer bearing an alkyne terminated tether. Click chemistry of these two components created a conjugate vaccine that induced antibodies to all three epitopes of the fully synthetic construct. We describe the challenges of building a fully synthetic vaccine and the features that appear to be important for optimizing a robust immune response.

Title: Carriers for Glycoconjugate Vaccines
Authors: Francesca Micoli *, Paolo Costantino and Roberto Adamo
Affiliation: GSK Vaccines Institute for Global Health (GVGH) S.r.l., Via Fiorentina 1, 53100 Siena, Italy
Email: francesca.x.micoli@gsk.com

Title: Why O-Acetylation Has a Role in the Immuno Response Evoked by Some Bacterial Polysaccharide-based Vaccines?
Authors: Francesco Berti, Riccardo De Ricco and Rino Rappuoli *
GSK Vaccines, Siena, Italy
Email: rino.x.rappuoli@gsk.com
Abstract: The incidence of infectious diseases caused by several bacterial pathogens (Haemophilus influenzae type b, Streptococcus pneumoniae and Neisseria meningitidis) has been dramatically reduced over the last 25 years by implementing vaccination campaigns with glycoconjugate vaccines. The structure of the bacterial capsular polysaccharide (CPS) antigens, most of them extracted and purified from microbial cultures and obtained with very high purity, has been deeply investigated at atomic level. O-acetyl group is one of the common ‘decorative’ groups of CPS antigens, which has been considered as an aspect of ‘structural identity’, might plays a key role in the immune responses evoked by these CPSs antigens. This review discusses the O-acetylation status of CPSs and its role in the immunological responses of these antigens.
Keywords: Bacterial vaccines, conjugate vaccines, carbohydrate antigens, O-acetylation


Title: Generation and Characterization of Antibodies against Glyco-Gold Nanoparticles Bearing a Synthetic Hexaarabinofuranoside Epitope Related to the Mycobacterial Lipoarabinomannan and Arabinogalactan
Authors: Gennady Burygin 1,2,*, Polina Abronina 3, Nikita Podvalnyy 3, Sergey Staroverov 1, Leonid Kononov 3 and Lev Dykman 1
Affiliation: 1. Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Prospekt Entuziastov 13, 410049 Saratov, Russia; burygingl@gmail.com (G.B.); staroverovsergey@me.com (S.S.); dykman_l@ibppm.ru (L.D.)
2. N. I. Vavilov Saratov State Agrarian University, 1 Teatralnaya Ploshchad, 410012 Saratov, Russia; burygingl@gmail.com (G.B.)
3.  N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospekt 47, 119991 Moscow, Russia; leonid.kononov@gmail.com (L.K.); polina-abronina@yandex.ru (P.A.); nmpodvalnyy@gmail.com (N.P.)
*  Correspondence: burygingl@gmail.com; Tel.: +007-927-145-6000
Abstract: Bacterial glycans are specific markers for detection and serological identification of microorganisms and are widely used as antigenic components of vaccines. The use of gold nanoparticles as carriers for glyco-epitopes is becoming an important alternative to the traditional conjugation with proteins and synthetic polymers. In this study, we aimed at preparation and characterization of antibodies against glyco-gold nanoparticles (glyco-GNPs) bearing the terminal branched hexaarabinofuranoside fragment (Ara6) of arabinan domains of lipoarabinomannan and arabinogalactan, which are principal polysaccharides of the cell wall of Mycobacterium tuberculosis, the causative agent of tuberculosis. Two synthetic Ara6 glycosides with amino-functionalized spacer aglycons differing in length and hydrophilicity were conjugated with gold nanospheres (d = 15 nm) to give two sets of glyco-GNPs which were used for immunization of rabbits. Dot assay revealed cross-reactions for the two obtained antisera with the hexaarabinofuranoside with 2-aminoethyl aglycon used for the preparation of glyco-GNPs. Both antisera contained high titers of antibodies specific for Mycobacteria as shown by enzyme-linked immunosorbent assay using M. bovis and M. smegmatis cells as antigens while gave a weak response with M. phlei cells and no interaction with E. coli cells. The results obtained suggest that glyco-GNPs are promising agents for generation of anti-mycobacterial antibodies.
Keywords: Mycobacterium; lipoarabinomannan; arabinogalactan; spacer aglycon; gold nanoparticles; conjugation of glycosides; antibody; dot assay; ELISA

Title: Recent Advances in the Synthesis of Glycoconjugates for Vaccine Development
Authors: Cinzia Colombo, Olimpia Pitirollo and Luigi Lay *
Affiliation: Department of Chemistry, University of Milan, Via C. Golgi 19, 20133 Milan, Italy
Email: luigi.lay@unimi.it
Abstract: During the last decade there has been a growing interest towards glycoimmunology, a relatively new research field dealing with the peculiar interactions of carbohydrates with the immune system. Pathogens cell surface is covered by a thick layer of oligo and polysaccharides that are crucial virulence factors, as they mediate receptors binding on host cells for initial adhesion and organism invasion. Since in most cases these saccharide structures are uniquely exposed on pathogens surface, they represent attractive targets for vaccine design. Accordingly, polysaccharides isolated from cell walls of microorganisms and chemically conjugated to immunogenic proteins have been used as antigens for vaccine development for a range of infectious diseases, including meningitis, pneumonia and enteric infections, just to mention a few. Several challenges are however associated to carbohydrate antigens purified from natural sources, such as difficult characterization and heterogeneous composition. Consequently, glycoconjugates based on fully synthetic saccharide antigens with chemically well-defined structures, able to confer highly reproducible biological properties and better safety profile, are at the forefront of vaccine development. Following up our previous review on the subject, in the present account we specifically focus on the most recent advances in the synthesis, protein conjugation and preliminary immunological evaluation of future generation glycoconjugate vaccines suitably designed to target bacterial and fungal infections and reported in the literature from 2011 on.

Title: Structure-Immunogenicity Relationship of alpha- and beta-Tetrasaccharide Glycoforms from Bacillus Anthracis Exosporium and Thereof Fragments
Authors: Riccardo De Ricco, Christy Ventura, Filippo Carboni, Pavol Kovac, Allison O’Brien, Roberto Adamo *
Affiliation: GSK Vaccines, Siena, Italy
Email: roberto.x.adamo@gsk.com

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