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Taxonomic group: bacteria / Actinobacteria (Phylum: Actinobacteria)

The structure was elucidated in this paper
NCBI PubMed ID: 2223004
Publication DOI: 10.1139/o90-112
Journal NLM ID: 8606068
Publisher: Ottawa: National Research Council of Canada
Institutions: Division of Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada

The specific capsular polysaccharide produced by Rhodococcus equi serotype 1 was found to be a high molecular weight acidic polymer composed of D-glucose, D-mannose, and D-glucuronic acid. Structural analysis of the polysaccharide employed a combination of chemical and nuclear magnetic resonance techniques, from which it was determined that the polysaccharide possessed a linear repeating tetrasaccharide unit containing a single 0-acetyl substituent and an acetal-linked pyruvic acid moiety: . The 1H and 13C nuclear magnetic resonances of 0-deacetylated and pyruvic-free serotype 1 polysaccharides were fully assigned by homo- and heteronuclear chemical shift correlation methods.

capsular polysaccharide, structural analysis, Rhodococcus equi

Structure type: polymer chemical repeating unit
Location inside paper: 1, Scheme 1, Table 5
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_137485,IEDB_140630,IEDB_142488,IEDB_144983,IEDB_146664,IEDB_152206,IEDB_423153,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_72

Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, GLC-MS, NMR-2D, acid hydrolysis, GLC, HPLC, gel filtration chromatography, O-deacetylation, gel immunodifusion test
Comments, role: NMR data for a de-O-acetylated sample; 13C NMR data for C3-C5 of 4-acetylated bDGlcpA were not available (for de-O-acetylated they are 84.91, 70.77, 73.7)

NCBI Taxonomy refs (TaxIDs): 43767
Show glycosyltransferases

NMR conditions: in D2O at 330 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4,3,4,4	Ac
4,3,4	bDGlcpA	103.35	73.74	?	?	?	?
4,3	bDGlcp	100.29	73.74	75.22	79.95	76.06	61.26
4,6	xSPyr	?	103.04	25.60
4	bDManp	101.57	69.34	76.82	73.46	67.25	65.62
	bDGlcpA	103.60	74.94	74.90	81.30	73.7	?

¹H NMR data: present in publication

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
4,3,4,4	Ac
4,3,4	bDGlcpA	103.35	73.74	?	?	?	?
4,3	bDGlcp	100.29	73.74	75.22	79.95	76.06	61.26
4,6	xSPyr	?	103.04	25.60
4	bDManp	101.57	69.34	76.82	73.46	67.25	65.62
	bDGlcpA	103.60	74.94	74.90	81.30	73.7	?

The spectrum also has 6 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

[*]O[C@H]1[C@H](OC(C)=O)[C@@H](C(=O)O)O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@H](O)[C@H](O[C@@H]4[C@@H](C(=O)O)O[C@@H]([*])[C@H](O)[C@H]4O)O[C@@H]4CO[C@@](C)(C(=O)O)O[C@H]43)[C@H](O)[C@H]2O)[C@@H]1O

SVG MW SMILES 3D mol Ionize