Synthesis of asparagine-linked bacillosamine.
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.
Amin
Mohammed Nurul
MN
RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama, Japan.
Ishiwata
Akihiro
A
Ito
Yukishige
Y
D001216:Asparagine / Q000737:chemistry*; D001426:Bacterial Proteins / Q000138:chemical synthesis / Q000737:chemistry; D016123:Campylobacter jejuni / Q000737:chemistry; D002240:Carbohydrate Sequence; D006023:Glycoproteins / Q000138:chemical synthesis / Q000737:chemistry; D006031:Glycosylation; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011135:Polysaccharides, Bacterial / Q000032:analysis / Q000737:chemistry
D001426:Bacterial Proteins; D006023:Glycoproteins; D006595:Hexosamines; D011135:Polysaccharides, Bacterial; D001216:Asparagine; C013920:4-deoxyneosamine C