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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: 16697990
Publication DOI: 10.1016/j.carres.2006.04.031
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: yukito

riken.jp
Institutions: RIKEN (The Institute of Physical and Chemical Research), Wako, Japan, Graduate School of Science and Engineering, Saitama University, Sakura-ku, Saitama 338-8570, Japan, CREST, Japan Science and Technology Agency (JST), Kawaguchi, Saitama 332-1102, Japan

Various types of protein glycosylation have been identified from prokaryotes. Recent investigations have revealed the presence of N-linked glycoproteins in the pathogenic bacterium, Campylobacter jejuni. The structure of this glycan is unique, consisting of 5 GalNAc and 1 Glc, in addition to 2,4-diacetamido-2,4,6-trideoxy-d-glucopyranose (bacillosamine; Bac), which is N-glycosidically linked to the side chain of asparagine (Asn). We synthesized Bac from a 2-azido-2-deoxy-d-galactose derivative, which was further converted to the Asn-linked form.

Campylobacter jejuni, bacillosamine, N-Linked glycoprotein

Structure type: oligomer
Location inside paper: p.1923,fig.1 (1)
Aglycon: protein PEB3 / Cj0289c
Compound class: N-glycan
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_142488,IEDB_146664,IEDB_885822,IEDB_983931,SB_192

Methods: chemical synthesis
Synthetic data: chemical

Related record ID(s): 20342
NCBI Taxonomy refs (TaxIDs): 197
Reference(s) to other database(s): GlycomeDB:27864
Show glycosyltransferases

There is only one chemically distinct structure:

CC(=O)N[C@H]1[C@@H](O[C@H]2[C@H](N)[C@@H](C)O[C@@H](NC(=O)CC(N)C(=O)O)[C@@H]2N)O[C@H](CO)[C@H](O[C@H]2O[C@H](CO)[C@H](O[C@H]3O[C@H](CO)[C@H](O[C@H]4O[C@H](CO)[C@H](O[C@H]5O[C@H](CO)[C@H](O)[C@H](O)[C@H]5NC(C)=O)[C@H](O)[C@H]4NC(C)=O)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]3NC(C)=O)[C@H](O)[C@H]2NC(C)=O)[C@@H]1O

SVG MW SMILES 3D mol Ionize