Recent Trends in Carbohydrate Chemistry: Synthesis and Biomedical Applications of Glycans and Glycoconjugates

Description

Recent Trends in Carbohydrate Chemistry: Synthesis and Biomedical Applications of Glycans and Glycoconjugates covers biomedically relevant bacterial cell wall carbohydrates including recent findings on biosynthetic aspects, advances in the chemical assembly of bacterial lipopolysaccharide fragments and teichoic acids, and modern NMR approaches to unravel structural details. The first part introduces and provides the relevant background for synthetic glycoconjugate vaccines. The second section focuses on synthetic carbohydrate-based vaccines of therapeutic potential that are licensed or under development. This second volume of Recent Trends in Carbohydrate Chemistry is ideal for researchers working as synthetic organic chemists, as well as those interested in glycoconjugation, protein chemists, immunologists, and microbiologists, in academia as well as in industry. Front Matter Copyright Contributors Preface Prokaryotes: Sweet proteins do matter Introduction Cell surface (S-) layer glycoproteins Bacteria Lactic acid bacteria Lactobacillus buchneri Lactobacillus kefiri Oral pathogens Tannerella forsythia Porphyromonas gingivalis Other bacteria Paenibacillus alvei Bacillus anthracis Kuenenia stuttgartiensis Candidatus Brocadia Archaea Haloferax volcanii Sulfolobus acidocaldarius Antarctic haloarchaea Flagella/Archaella and fimbriae Bacteria Paenibacillus alvei Selenomonas sputigena Porphyromonas gingivalis Archaea Haloferax volcanii Adhesins, bacteriocins, invasins, and glycocins Streptococcus gordonii Streptococcus salivarius Streptococcus agalactiae Streptococcus mutans Staphylococcus aureus Enterococcus durans Lactobacillus plantarum Lactobacillus casei Xanthomonas citri Escherichia coli Actinoplanes sp. Trichomonas vaginalis Spores Bacillus anthracis Concluding remarks References Glycan ligation reactions in the periplasmic space Introduction WaaL O-antigen ligases The ArnT family Oligosaccharyl transferases Conclusions References Synthesis of bioactive lipid A and analogs Lipid A—Structure, immunobiological function, and potential therapeutic significance Lipopolysaccharide and lipid A are “pathogen-associated molecular patterns” Lipid A regulates the innate immune signaling through “PRRs” TLR4 and caspase-4/11 Structural diversity of lipid A Challenges in endotoxin research and heterogeneity of lipid A Synthesis of lipid A and analogs Approaches toward the synthesis of lipid A variants Synthesis of orthogonally protected β (1 → 6)-linked diglucosamine backbone of lipid A. Protective group manipul ... Divergent s ynthesis of E. coli, S. typhimurium, and N. meningitidis lipid A Synthesis of a library of P. gingivalis lipid A and analogs Divergent synthesis of H. pylori lipid A variants Synthesis of structurally unusual lipid A from Rhizobium sin-1 Application of lipid A derivatives as vaccine adjuvants Synthesis of MPLA variants as potential vaccine adjuvants Application of MPLA as carrier molecule and “inbuilt” adjuvant for self-adjuvanting vaccine candidates Synthesis of lipid A modified by addition of amino sugars at the glycosidic phosphate group Synthetic challenges in the assembly of 1,1 ′ -glycosyl phosphodiesters Galactosamine-modified Francisella lipid A Synthesis of a neoglycoconjugate comprising GalN-modified Francisella lipid A backbone β GlcN(1 → 6)- α GlcN(1 ... 4-Amino-4-deoxy- β - l -arabinose ( β - l -Ara4N)-modified Burkholderia lipid A Synthesis of a neoglycoconjugate entailing an epitope β GlcN(1 → 6)- α GlcN(1 → P←1)- β - l -Ara4N Synthesis of 4-amino-4-deoxy- β - l -arabinose ( β - l -Ara4N)-modified Burkholderia lipid A Conclusion References Synthesis of lipopolysaccharide core fragments Introduction Synthesis of LPS inner core fragments Recent approaches for Kdo α-glycoside formation Synthesis of Kdo β-glycosides Synthesis of LPS inner core fragments of Acinetobacter and Agrobacteria Synthesis of inner core units containing Ko and Ara4N residues Synthesis of heptose-containing core fragments Synthesis of glycero-d-manno-heptoses Synthesis of heptose-containing inner core units Synthesis of Neisseria and Haemophilus core epitopes Synthesis of outer core fragments Conclusions Acknowledgment References Synthesis of oligosaccharides related to potential bioterrorist pathogens Introduction Bacillus anthracis Burkholderia pseudomallei and Burkholderia mallei Capsular polysaccharides Lipopolysaccharides Exopolysaccharides Francisella tularensis Yersinia pestis Brucella spp. Conclusion References Synthetic teichoic acid chemistry for vaccine applications Introduction Synthetic teichoic acids S. aureus TAs S. aureus LTA S. aureus WTA Enterococcal TAs E. faecalis and E. faecium LTA E. faecium WTA C. difficile C. difficile LTA (PSIII) Conclusions References NMR characterization of bacterial glycans and glycoconjugate vaccines NMR characterization of carbohydrates Carbohydrate NMR spectra Assignment of NMR spectra of carbohydrates NMR analysis of surface carbohydrates of gram-negative bacteria Capsular polysaccharides Lipopolysaccharide Shigella O-antigens Salmonella O-antigens NMR analysis of surface carbohydrates of gram-positive bacteria Surface carbohydrates of Streptococcus pneumoniae Surface carbohydrates of group B Streptococcus Surface carbohydrates of other gram-positive bacteria NMR analysis of glycoconjugate vaccines Preparation of glycoconjugate vaccines NMR monitoring of the conjugation process NMR characterization of glycoconjugate vaccines Investigating antigen-antibody interactions using NMR spectroscopy Conclusions Acknowledgments References Glycoconjugate vaccines, production and characterization Introduction Conjugation chemistries Classic methods for conjugation of natural polysaccharides and synthetic carbohydrates Site-selective glycan-protein conjugation Conjugation to nanoparticle carriers Physicochemical characterization and quality control of glycoconjugate vaccines Conclusions Disclosures References Antifungal glycoconjugate vaccines Introduction Major human fungal pathogens Carbohydrates in the molecular architecture of fungal CWs Immunity against fungal pathogens Glycoconjugates as antifungal vaccines Glycoconjugates vaccines against Candida Mannan glycoconjugates β -Glucan glycoconjugates Poly- N -acetyl-(1 → 6)- α -glucosamine glycoconjugates Glycoconjugates vaccines against Aspergillus fumigatus Glycoconjugates vaccines against Cryptococcus neoformans Conclusion References Site-selective conjugation chemistry for synthetic glycoconjugate vaccine development Introduction Homogeneous glycoprotein vaccine design Classical bioconjugation methods Modern methods targeting canonical amino acids Lysine and N-terminus Tyrosine Cysteine and disulfides Modern methods targeting noncanonical amino acids Carbonyls Alkynes, alkenes, and dipoles Transition metal-mediated approaches Canonical amino acids Noncanonical amino acids Conclusions and outlook Acknowledgments References Glyconanoparticles as versatile platforms for vaccine development: A minireview Glyconanoparticles based on inorganic core Antiviral vaccines Antibacterial vaccines Anticancer vaccines Glyconanoparticles based on polymeric core Glyconanoparticles based on self-assembling core Glyconanoparticles based on OMVs Glyconanoparticles based on virus-like particles Conclusions References Index A B C D E F G H I K L M N O P Q R S T U V W X Y Z