Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: infection due to Streptococcus pneumoniae [ICD11:
XN3PW 
]
NCBI PubMed ID: 31546911Publication DOI: 10.3390/molecules24183414Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: felicia.dandrea
unipi.it; lorenzo.guazzelli
unipi.it
Institutions: Dipartimento di Farmacia, University of Pisa, Via Bonanno 6/33, 56126 Pisa, Italy, Dipartimento di Scienze del Farmaco, University of Piemonte Orientale Amedeo Avogadro, Largo Donegani 2, 28100 Novara, Italy
Zwitterionic polysaccharides (ZPs) have been shown in recent years to display peculiar immunological properties, thus attracting the interest of the carbohydrate research community. To fully elucidate the mechanisms underlying these properties and exploit the potential of this kind of structures, in depth studies are still required. In this context, the preparation of two cationic, an anionic, as well as two zwitterionic tetrasaccharide analogues of the smallest immunogenic structure of Streptococcus pneumoniae type 14 (SP14) capsular polysaccharide are presented. By exploiting a block strategy, the negative charge has been installed on the non-reducing end of the lactose unit of the tetrasaccharide and the positive charge either on the non-reducing end of the lactosamine moiety or on an external linker. These structures have then been tested by competitive ELISA, showing that the structural variations we made do not modify the affinity of the neutral compound to binding to a specific antibody. However, lower efficacies than the natural SP14 compound were observed. The results obtained, although promising, point to the need to further elongate the polysaccharide structure, which is likely too short to cover the entire epitopes.
Streptococcus pneumoniae type 14, competitive ELISA, zwitterionic analogues
Structure type: fragment of a bigger structure
Location inside paper: fig.1, structure 1 of SP14 CPS
Trivial name: repeating unit of CPS
Compound class: CPS
Contained glycoepitopes: IEDB_130646,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149138,IEDB_149143,IEDB_151531,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_30,SB_6,SB_7,SB_88
Methods: 13C NMR, 1H NMR, TLC, ELISA, chemical synthesis, chemical methods, UV, glycosylation, optical rotation measurement, statistical analysis, flash chromatography
NCBI Taxonomy refs (TaxIDs): 1313Reference(s) to other database(s): GTC:G09494DM
Show glycosyltransferases
There is only one chemically distinct structure:
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