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Synthesis of N-linked glycan derived from Gram-negative bacterium, Campylobacter jejuni |
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| Authors: | Mohammed Nurul Amin Akihiro Ishiwata Yukishige Ito |
| Affiliation: | a RIKEN (The Institute of Physical and Chemical Research), 2-1 Hirosawa, Wako, Saitama 351-0198, Japan b Graduate School of Science and Engineering, Saitama University, Sakura-ku, Saitama 338-8570, Japan c CREST, JST, Kawaguchi, Saitama 332-0012, Japan |
| Abstract: | Recent research has revealed the presence of asparagine (Asn)-linked (N-linked) glycoproteins in certain prokaryotes. In this paper, we describe the chemical synthesis of a novel N-glycan derived from Campylobacter jejuni, a heptasaccharide composed of Asn-linked bacillosamine (Bac), repeating GalNAc, and branching Glc, namely GalNAc-α(1,4)-GalNAc-α(1,4)-[Glc-β(1,3)-]GalNAc-α(1,4)-GalNAc-α(1,4)-GalNAc-α(1,3)-Bac. The synthesis started from a Bac-acceptor, which was consecutively glycosylated with 4-O-pentafluoropropionyl (PFP) protected donors to give heptasaccharide. Reduction of azide groups was followed by debenzylation to complete the synthesis of the target oligosaccharide. |
| Keywords: | Bacterial N-glycan Campylobacter jejuni Stereoselective 1,2-cis glycosylation Heptasaccharide |
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