Show legend Show as text

Structure type: oligomer
Trivial name: repeating unit
Compound class: CPS
Contained glycoepitopes: IEDB_1075132,IEDB_120354,IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141588,IEDB_141794,IEDB_141807,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_68,SB_7,SB_84,SB_88

• Article ID: 4776
  Mondal PK, Liao G, Mondal MA, Guo Z "Chemical synthesis of the repeating unit of type ia group B streptococcus capsular polysaccharide" - Organic Letters 17(5) (2015) 1102-1105
  

  The structure of the capsular polysaccharide (CPS) of serotype Ia group B Streptococcus (GBS) has been characterized for years, but its repeating unit, which is a challenging pentasaccharide with a branch and a difficult α-sialic acid linkage, has not been synthesized yet. In this report, an effective synthesis was developed for the serotype Ia GBS CPS repeating unit, which had a reactive functionality linked to its main-chain reducing end to enable further elaboration, such as coupling with carrier proteins. The target molecule was accomplished by a convergent [2 + 3] glycosylation strategy employing a sialo-disaccharide as donor and a branched trisaccharide as acceptor. The strategy was designed to suit the synthesis of oligomers of the repeating unit.

  capsular polysaccharide, glycosylation, Streptococcus agalactiae

  NCBI PubMed ID: 25674920
  Publication DOI: 10.1021/ol5036563
  Journal NLM ID: 100890393
  Publisher: American Chemical Society
  Correspondence: zwguo@chem.wayne.edu
  Institutions: Department of Chemistry, Wayne State University , 5101 Cass Avenue, Detroit, Michigan 48202, United States
  Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, MALDI-TOF MS, NMR-1D, glycosylation
  
   
  
  Streptococcus agalactiae B Ia
  CSDB ID 30818 (all data & tools)
• Article ID: 6211
  Del Bino L, Osterlid KE, Wu DY, Nonne F, Romano MR, Codée J, Adamo R "Synthetic Glycans to Improve Current Glycoconjugate Vaccines and Fight Antimicrobial Resistance" - Chemical Reviews 122(20) (2022) 15672-15716
  

  Antimicrobial resistance (AMR) is emerging as the next potential pandemic. Different microorganisms, including the bacteria Acinetobacter baumannii, Clostridioides difficile, Escherichia coli, Enterococcus faecium, Klebsiella pneumoniae, Neisseria gonorrhoeae, Pseudomonas aeruginosa, non-typhoidal Salmonella, and Staphylococcus aureus, and the fungus Candida auris, have been identified by the WHO and CDC as urgent or serious AMR threats. Others, such as group A and B Streptococci, are classified as concerning threats. Glycoconjugate vaccines have been demonstrated to be an efficacious and cost-effective measure to combat infections against Haemophilus influenzae, Neisseria meningitis, Streptococcus pneumoniae, and, more recently, Salmonella typhi. Recent times have seen enormous progress in methodologies for the assembly of complex glycans and glycoconjugates, with developments in synthetic, chemoenzymatic, and glycoengineering methodologies. This review analyzes the advancement of glycoconjugate vaccines based on synthetic carbohydrates to improve existing vaccines and identify novel candidates to combat AMR. Through this literature survey we built an overview of structure-immunogenicity relationships from available data and identify gaps and areas for further research to better exploit the peculiar role of carbohydrates as vaccine targets and create the next generation of synthetic carbohydrate-based vaccines.

  carbohydrates, glycan, glycoconjugate vaccine

  NCBI PubMed ID: 35608633
  Publication DOI: 10.1021/acs.chemrev.2c00021
  Journal NLM ID: 2985134R
  Publisher: Chem Rev
  Correspondence: J. Codée ; R. Adamo
  Institutions: GSK, R&D, 53100 Siena, Italy, Leiden Institute of Chemistry, Leiden University, 2300 RA Leiden, The Netherlands
  
   
  
  Streptococcus agalactiae B Ia
  CSDB ID 20898 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_1075132,IEDB_1075133,IEDB_120354,IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_1391966,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141588,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151531,IEDB_190606,IEDB_423120,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_39,SB_6,SB_68,SB_7,SB_84,SB_88

• Article ID: 5806
  Li R, Yu H, Chen X "Recent progress in chemical synthesis of bacterial surface glycans" - Current Opinion in Chemical Biology 58 (2020) 121-136
  

  With the continuing advancement of carbohydrate chemical synthesis, bacterial glycomes have become increasingly attractive and accessible synthetic targets. Although bacteria also produce carbohydrate-containing secondary metabolites, our review here will cover recent chemical synthetic efforts on bacterial surface glycans. The obtained compounds are excellent candidates for the development of improved structurally defined glycoconjugate vaccines to combat bacterial infections. They are also important probes for investigating glycan–protein interactions. Glycosylation strategies applied for the formation of some challenging glycosidic bonds of various uncommon sugars in a number of recently synthesized bacterial surface glycans are highlighted.

  synthesis, carbohydrate, glycosyltransferase, glycoconjugate vaccine, Bacterial glycan

  NCBI PubMed ID: 32920523
  Publication DOI: 10.1016/j.cbpa.2020.08.003
  Journal NLM ID: 9811312
  Publisher: London: Elsevier
  Correspondence: Chen Xi
  Institutions: Department of Chemistry, University of California Davis, Davis, CA, USA
  
   
  
  Streptococcus sp. Ia
  CSDB ID 5082 (all data & tools)