Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: pneumonia [ICD11:
CA40 
];
meningitis [ICD11:
1D01 ];
endocarditis [ICD11:
BB40 , ICD11:
BB4Z ];
septicemia [ICD11:
MA15.Y ];
infection due to Streptococcus pneumoniae [ICD11:
XN3PW ]
NCBI PubMed ID: 27559395Publication DOI: 10.3762/bjoc.12.139Journal NLM ID: 101250746Publisher: Beilstein-Institut
Correspondence: peter.seeberger
mpikg.mpg.de
Institutions: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476 Potsdam, Germany and Department of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany
Vaccines against S. pneumoniae, one of the most prevalent bacterial infections causing severe disease, rely on isolated capsular polysaccharide (CPS) that are conjugated to proteins. Such isolates contain a heterogeneous oligosaccharide mixture of different chain lengths and frame shifts. Access to defined synthetic S. pneumoniae CPS structures is desirable. Known syntheses of S. pneumoniae serotype 3 CPS rely on a time-consuming and low-yielding late-stage oxidation step, or use disaccharide building blocks which limits variability. Herein, we report the first iterative automated glycan assembly (AGA) of a conjugation-ready S. pneumoniae serotype 3 CPS trisaccharide. This oligosaccharide was assembled using a novel glucuronic acid building block to circumvent the need for a late-stage oxidation. The introduction of a washing step with the activator prior to each glycosylation cycle greatly increased the yields by neutralizing any residual base from deprotection steps in the synthetic cycle. This process improvement is applicable to AGA of many other oligosaccharides.
Streptococcus pneumoniae, Oligosaccharides, glycosylation, protecting groups, automation, solid-phase synthesis
Structure type: polymer chemical repeating unit
Location inside paper: p.1441, fig.1
Compound class: CPS, EPS, glucan, polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_149553,IEDB_423153,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, IR, TLC, chemical synthesis, MALDI-TOF MS, HPLC, UV, glycosylation
NCBI Taxonomy refs (TaxIDs): 1313Reference(s) to other database(s): GTC:G48944PP, GlycomeDB:
25551, CCSD:
45515, CBank-STR:3690
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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