Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: urinary tract infections (UTI) [ICD11:
GC08 
]
The structure was elucidated in this paperNCBI PubMed ID: 20639341Publication DOI: 10.1128/JB.00104-10Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: jclee
rics.bwh.harvard.edu
Institutions: Channing Laboratory, Department of Medicine, Brigham and Women's Hospital and Harvard Medical School, Boston, Massachusetts 02115, USA
Staphylococcus saprophyticus is a common cause of uncomplicated urinary tract infections in women. S. saprophyticus strain ATCC 15305 carries two staphylococcal cassette chromosome genetic elements, SCC(15305RM) and SCC(15305cap). The SCC(15305cap) element carries 13 open reading frames (ORFs) involved in capsular polysaccharide (CP) biosynthesis, and its G+C content (26.7%) is lower than the average G+C content (33.2%) for the whole genome. S. saprophyticus strain ATCC 15305 capD, capL, and capK (capD(Ssp), capL(Ssp), and capK(Ssp)) are homologous to genes encoding UDP-FucNAc biosynthesis, and gtaB and capI(Ssp) show homology to genes involved in UDP-glucuronic acid synthesis. S. saprophyticus ATCC 15305 CP, visualized by immunoelectron microscopy, was extracted and purified using anionic-exchange and size exclusion chromatography. Analysis of the purified CP by (1)H and (13)C nuclear magnetic resonance (NMR) spectroscopy and gas-liquid chromatography revealed two types of branched tetrasaccharide repeating units composed of the following: -4)-β-Glc-(1-3)-[β-GlcNAc-(1-2)]Sug-(1-4)-β-GlcA-(1-: Sug represents two stereoisomers of 2-acetamido-2,6-dideoxy-hexos-4-ulose residues, one of which has an arabino configuration. The encapsulated ATCC 15305 strain was resistant to complement-mediated opsonophagocytic killing by human neutrophils, whereas the acapsular mutant C1 was susceptible. None of 14 clinical isolates reacted with antibodies to the ATCC 15305 CP. However, 11 of the 14 S. saprophyticus isolates were phenotypically encapsulated based on their resistance to complement-mediated opsonophagocytic killing and their failure to hemagglutinate when cultivated aerobically. Ten of the 14 clinical strains carried homologues of the conserved staphylococcal capD gene or the S. saprophyticus gtaB gene, or both. Our results suggest that some strains of S. saprophyticus are encapsulated and that more than one capsular serotype exists.
Bacterial, polysaccharides, Staphylococcus, Bacterial Capsules
Structure type: polymer chemical repeating unit
Location inside paper: p.4622, fig.4, table S2
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_423153,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, DNA techniques, GLC, methanolysis, genetic methods, immunoelectron microscopy
Biological activity: phenotypic analysis data, opsonophagocytic killing assay
Comments, role: Sug represents two stereoisomers of 2-acetamido-2,6-dideoxy-hexos-4-ulose residues, one of which has a β-arabino configuration (residue D: b?6daraHexpN-4-ulo = SMILES O=C1[C@@H](C)C{1}[C@@H](O){2}[C@H](N){3}[C@H]1O). NMR data for the sequence -[A]F-D-K- fig.4.
NCBI Taxonomy refs (TaxIDs): 342451
Show glycosyltransferases
NMR conditions: in D2O at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,3,2,2 Ac
4,3,2 bDGlcpN 102.7 56.9 75.0 71.8 77.1 62.7
4,3 bDGlcp 103.4 80.3 76.2 81.6 ? 61.9
4,2 Ac
4 ??Sugp 100.6 52.2 84.4 93.6 72.7 12.5
bDGlcpA 103.6 73.7 75.0 81.3 76.0 ?
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,3,2,2 Ac
4,3,2 bDGlcpN 4.83 3.66 3.57 3.35 3.47 3.66-3.97
4,3 bDGlcp 4.66 3.78 3.70 3.79 ? 3.76-3.89
4,2 Ac
4 ??Sugp 4.72 4.07 3.88 - 4.13 1.26
bDGlcpA 4.56 3.38 3.64 3.71 3.95 -
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,3,2,2 Ac
4,3,2 bDGlcpN 102.7/4.83 56.9/3.66 75.0/3.57 71.8/3.35 77.1/3.47 62.7/3.66-3.97
4,3 bDGlcp 103.4/4.66 80.3/3.78 76.2/3.70 81.6/3.79 ?/? 61.9/3.76-3.89
4,2 Ac
4 ??Sugp 100.6/4.72 52.2/4.07 84.4/3.88 72.7/4.13 12.5/1.26
bDGlcpA 103.6/4.56 73.7/3.38 75.0/3.64 81.3/3.71 76.0/3.95
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,3,2,2 | Ac | |
| 4,3,2 | bDGlcpN | 4.83 | 3.66 | 3.57 | 3.35 | 3.47 | 3.66
3.97 |
| 4,3 | bDGlcp | 4.66 | 3.78 | 3.70 | 3.79 | ? | 3.76
3.89 |
| 4,2 | Ac | |
| 4 | ??Sugp | 4.72 | 4.07 | 3.88 |
| 4.13 | 1.26 |
| | bDGlcpA | 4.56 | 3.38 | 3.64 | 3.71 | 3.95 |
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,3,2,2 | Ac | |
| 4,3,2 | bDGlcpN | 102.7 | 56.9 | 75.0 | 71.8 | 77.1 | 62.7 |
| 4,3 | bDGlcp | 103.4 | 80.3 | 76.2 | 81.6 | ? | 61.9 |
| 4,2 | Ac | |
| 4 | ??Sugp | 100.6 | 52.2 | 84.4 | 93.6 | 72.7 | 12.5 |
| | bDGlcpA | 103.6 | 73.7 | 75.0 | 81.3 | 76.0 | ? |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":102.7,"l":"1","c":[0,0,225]},{"s":56.9,"l":"2","c":[0,0,225]},{"s":75,"l":"3","c":[0,0,225]},{"s":71.8,"l":"4","c":[0,0,225]},{"s":77.1,"l":"5","c":[0,0,225]},{"s":62.7,"l":"6","c":[0,0,225]},{"s":103.4,"l":"1","c":[230,0,30]},{"s":80.3,"l":"2","c":[230,0,30]},{"s":76.2,"l":"3","c":[230,0,30]},{"s":81.6,"l":"4","c":[230,0,30]},{"s":61.9,"l":"6","c":[230,0,30]},{"s":100.6,"l":"1","c":[0,165,0]},{"s":52.2,"l":"2","c":[0,165,0]},{"s":84.4,"l":"3","c":[0,165,0]},{"s":93.6,"l":"4","c":[0,165,0]},{"s":72.7,"l":"5","c":[0,165,0]},{"s":12.5,"l":"6","c":[0,165,0]},{"s":103.6,"l":"1","c":[120,0,225]},{"s":73.7,"l":"2","c":[120,0,225]},{"s":75,"l":"3","c":[120,0,225]},{"s":81.3,"l":"4","c":[120,0,225]},{"s":76,"l":"5","c":[120,0,225]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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