CSDB: Search results

Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Campylobacter jejuni [ICD11: XN4Q5

]

The structure was elucidated in this paper
NCBI PubMed ID: 17335095
Publication DOI: 10.1002/cbic.200600508
Journal NLM ID: 100937360
Publisher: Weinheim, Germany: Wiley Interscience
Correspondence: evguenii.vinogradov

nrc.ca
Institutions: Institute for Biological Sciences, National Research Council Canada, 100 Sussex Drive, Ottawa, K1A 0R6, Canada

The complete genome of Campylobacter jejuni strain RM1221 (Penner serotype HS:53) was reported recently and contains a novel capsular polysaccharide (CPS) biosynthesis locus. Cell-surface carbohydrates such as CPS are known to be important for bacterial survival and often contribute to pathogenesis. In this study, we describe the complete structure of the CPS of C. jejuni RM1221, which was determined by using NMR spectroscopy, MS, and chemical methods. The CPS contains 6-deoxy-D-manno-heptose and D-threo-pent-2-ulose (D-xylulose), two monosaccharides that are rarely found in bacterial polysaccharides. The CPS has a regular structure of a linear main chain of trisaccharide repeating units, composed of two α- and one β-6-deoxy-D-manno-heptopyranose residues, which are linked through a phosphodiester linkage. Branching residues of xylulose are incorporated nonstoichiometrically: each trisaccharide repeating unit of the main chain bears no, one, or two xylulose residues. The xylulose glycosidic linkages are extremely acid labile, and it is not clear how they can be preserved under the acidic conditions of the gastrointestinal tract, where Campylobacter resides during infection. We have also shown that the CPS biosynthesis genes of C. jejuni RM1221 are conserved in other C. jejuni strains of the Penner serotype HS:53, including serotype HS:53 reference strain RM3435

biosynthesis, capsular polysaccharide, Campylobacter jejuni, NMR spectroscopy

Structure type: oligomer
Location inside paper: p.626, scheme 1, 1

Methods: 13C NMR, methylation, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, mild acid hydrolysis, NMR-1D, genetic methods, CE-ESI-MS
Biosynthesis and genetic data: genetic data
Comments, role: mild acid hydrolysis of the CPS. 1H and 13C NMR data shown for aD6dmanHep? residue. NMRH for #0_bD6dmanHep? 4.87 4.08 3.72 3.57 3.42 1.71 3.7-3.8 // NMRC for #_bD6dmanHep? 4.9 72.2 81.3 71.2 73.9 34.5 59.6//

Related record ID(s): 21572, 21968, 21969
NCBI Taxonomy refs (TaxIDs): 195099
Reference(s) to other database(s): GTC:G59800TQ, GlycomeDB:35015
Show glycosyltransferases

NMR conditions: in D2O at 313 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7
3,3,3	P
3,3	bD6dmanHepp	98.1	71.5	78.7	70.9	74.2	34.5	59.6
3	aD6dmanHepp	103.2	68.5	78.7	70.2	70.8	34.5	59.6
	?D6dmanHep?	95.3	71.8	79.1	71.4	70.8	34.5	59.6


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
3,3,3	P
3,3	bD6dmanHepp	4.86	4.27	4.10	3.63	3.48	1.77	3.7-3.8
3	aD6dmanHepp	5.14	4.27	4.10	3.68	3.87	1.77	3.7-3.8
	?D6dmanHep?	5.11	4.06	3.89	3.64	3.89	1.71	3.7-3.8


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7
3,3,3	P
3,3	bD6dmanHepp	98.1/4.86	71.5/4.27	78.7/4.10	70.9/3.63	74.2/3.48	34.5/1.77	59.6/3.7-3.8
3	aD6dmanHepp	103.2/5.14	68.5/4.27	78.7/4.10	70.2/3.68	70.8/3.87	34.5/1.77	59.6/3.7-3.8
	?D6dmanHep?	95.3/5.11	71.8/4.06	79.1/3.89	71.4/3.64	70.8/3.89	34.5/1.71	59.6/3.7-3.8

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
3,3,3	P
3,3	bD6dmanHepp	4.86	4.27	4.10	3.63	3.48	1.77	3.7 3.8
3	aD6dmanHepp	5.14	4.27	4.10	3.68	3.87	1.77	3.7 3.8
	?D6dmanHep?	5.11	4.06	3.89	3.64	3.89	1.71	3.7 3.8

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7
3,3,3	P
3,3	bD6dmanHepp	98.1	71.5	78.7	70.9	74.2	34.5	59.6
3	aD6dmanHepp	103.2	68.5	78.7	70.2	70.8	34.5	59.6
	?D6dmanHep?	95.3	71.8	79.1	71.4	70.8	34.5	59.6

There are 3 chemically distinct structures. Please, select:

O=P(O)(O)O[C@@H]1[C@H](O)[C@H](O[C@@H]2[C@H](O)[C@@H](O[C@@H]3[C@H](O)C(O)O[C@H](CCO)[C@H]3O)O[C@H](CCO)[C@H]2O)O[C@H](CCO)[C@H]1O

SVG MW SMILES 3D mol Ionize