Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: pneumonia [ICD11:
CA40 
];
septicemia [ICD11:
MA15.Y ];
meningitis [ICD11:
1D01 ];
acute otitis media [ICD11:
AB00 , Life stage: adult];
infection due to Streptococcus pneumoniae [ICD11:
XN3PW ]
The structure was elucidated in this paperNCBI PubMed ID: 22328666Publication DOI: 10.1128/JB.06487-11Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Lu Feng <fenglu63
nankai.edu.cn>
Institutions: TEDA School of Biological Sciences and Biotechnology, Nankai University, Tianjin, China
Streptococcus pneumoniae is a major human pathogen associated with many diseases worldwide. Capsular polysaccharides (CPSs) are the major virulence factor. The biosynthetic pathway of D-arabinitol, which is present in the CPSs of several S. pneumoniae serotypes, has never been identified. In this study, the genes abpA (previously known as abp1) and abpB (previously known as abp2), which have previously been reported to be responsible for nucleoside diphosphate (NDP)-D-arabinitol (the nucleotide-activated form of D-arabinitol) synthesis, were cloned. The enzyme products were overexpressed, purified, and analyzed for their respective activities. Novel products produced by AbpA- and AbpB-catalyzing reactions were detected by capillary electrophoresis, and the structures of the products were elucidated using electrospray ionization mass spectrometry and nuclear magnetic resonance spectroscopy. As a result, abpA was identified to be a D-xylulose-5-phosphate cytidylyltransferase-encoding gene, responsible for the transfer of CTP to D-xylulose-5-phosphate (D-Xlu-5-P) to form CDP-D-xylulose, and abpB was characterized to be a CDP-D-xylulose reductase-encoding gene, responsible for the conversion of CDP-D-xylulose to CDP-D-arabinitol as the final product. The kinetic parameters of AbpA for the substrates D-Xlu-5-P and CTP and those of AbpB for the substrate CDP-D-xylulose and the cofactors NADH or NADPH were measured, and the effects of temperature, pH, and cations on the two enzymes were analyzed. This study confirmed the involvement of the genes abpA and abpB and their products in the biosynthetic pathway of CDP-D-arabinitol.
capsular polysaccharides, Streptococcus pneumoniae 17F, CDP-D-arabinitol, biosynthetic pathway
Structure type: monomer
Location inside paper: p.1870, fig 1, CDP-D-arabinitol
Trivial name: CDP-D-arabinitol
Contained glycoepitopes: IEDB_141494
Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, ESI-MS, GLC, genetic methods, enzymatic analysis, RP-HPLC, CE
Biological activity: kinetic data
Enzymes that release or process the structure: AbpB (Abp2), CDP-D-xylulose reductase
Synthetic data: enzymatic
Related record ID(s): 27350
NCBI Taxonomy refs (TaxIDs): 1313
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5
5,0,0 xDAra-ol 68.2 70.0 71.1 72.1 64.2
5,0 P
5 P
xXnucC
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5
5,0,0 xDAra-ol 4.02-4.04 4.09 3.66 3.76 3.66-3.84
5,0 P
5 P
xXnucC
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5
5,0,0 xDAra-ol 68.2/4.02-4.04 70.0/4.09 71.1/3.66 72.1/3.76 64.2/3.66-3.84
5,0 P
5 P
xXnucC
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 |
|---|
| 5,0,0 | xDAra-ol | 4.02
4.04 | 4.09 | 3.66 | 3.76 | 3.66
3.84 |
| 5,0 | P | |
| 5 | P | |
| | xXnucC | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 |
|---|
| 5,0,0 | xDAra-ol | 68.2 | 70.0 | 71.1 | 72.1 | 64.2 |
| 5,0 | P | |
| 5 | P | |
| | xXnucC | |
|
There is only one chemically distinct structure:
Found 
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