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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: cholera [ICD11: 1A00

, ICD11: XN7N1

]

The structure was elucidated in this paper
NCBI PubMed ID: 21899371
Publication DOI: 10.1021/bc2001984
Journal NLM ID: 9010319
Publisher: Washington, DC: American Chemical Society
Correspondence: P.K. <kpn

helix.nih.gov>; E.T.R. <etryan

partners.org>
Institutions: NIDDK, LBC, National Institutes of Health, Bethesda, MD, USA-0815, United States

Bacterial O-SP-core antigens can be conjugated to proteins in the same, simple way as synthetic, linker-equipped carbohydrates by applying squaric acid chemistry. Introduction of spacers (linkers) to either O-SP-core antigens or protein carriers, which is involved in commonly applied protocols, is not required. The newly developed method described here consists of preparation of a squaric acid monoester derivative of O-SP-core antigen, utilizing the amino group inherent in the core, and reaction of the monoester with the carrier protein. The intermediate monoester can be easily purified; its conjugation can be monitored by SELDI-TOF mass spectrometry and, thus, readily controlled, since the conjugation can be terminated when the desired carbohydrate-protein ratio is reached. Here, we describe production of conjugates containing the O-SP-core antigen of Vibrio cholerae O1, the major cause of cholera, a severe dehydrating diarrheal disease of humans. The resultant products are recognized by convalescent phase sera from patients recovering from cholera in Bangladesh, and anti-O-SP-core-protein responses correlate with plasma antilipopolysaccharide and vibriocidal responses, which are the primary markers of protection from cholera. The results suggest that such conjugates have potential as vaccines for cholera and other bacterial diseases.

Vibrio cholerae O1, conjugate vaccine

Structure type: oligomer
Location inside paper: abstract, p.2180, fig.1
Trivial name: OSP-core-spacer-BSA
Compound class: glycoconjugate
Contained glycoepitopes: IEDB_130664,IEDB_137779,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_161054,IEDB_161056,IEDB_161058,IEDB_2189047,IEDB_983931,SB_192

Methods: 13C NMR, mild acid hydrolysis, serological methods, conjugation, SELDI-TOF MS
Biological activity: evaluation of immunoreactivity of conjugates
Comments, role: Ogawa: with terminal Methyl, Inaba: without terminal Methyl

Related record ID(s): 26392, 27013
NCBI Taxonomy refs (TaxIDs): 127906
Show glycosyltransferases

There are 4 chemically distinct structures. Please, select:

[1*]Nc1c(N[C@H]2[C@@H](OC[C@H](O)[C@H]3O[C@H](O[C@H]4[C@@H](O)[C@H](O)[C@@H]([C@H](CO)O[C@H]5O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]5O)O[C@@H]4O[C@@H]4[C@H](O)[C@@H](O[C@@H]5[C@@H](CC(=O)C(=O)O)O[C@@H](CO)[C@H]5O)O[C@H]([C@H](CO)O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H]4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O[C@H]4O[C@H](C)[C@@H](NC(=O)[C@@H](O)CCO)[C@H](O)[C@@H]4O[C@H]4O[C@H](C)[C@@H](NC(=O)[C@@H](O)CCO)[C@H](O)[C@@H]4O[C@H]4O[C@H](C)[C@@H](NC(=O)[C@@H](O)CCO)[C@H](O)[C@@H]4O[C@H]4O[C@H](C)[C@@H](NC(=O)[C@@H](O)CCO)[C@H](O)[C@@H]4OC)[C@@H](O)[C@@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)c1=O

SVG MW SMILES 3D mol Ionize

R1 = BSA
Warning = sub-repeat ending at aDRhap4N: unknown unit count was assumed to be 3