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Structural Determination and Chemical Synthesis of the N-Glycan from the Hyperthermophilic Archaeon Thermococcus kodakarensis |
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| Authors: | Kohtaro Hirao Immacolata Speciale Anna Notaro Dr Yoshiyuki Manabe Yoshiaki Teramoto Dr Takaaki Sato Prof Haruyuki Atomi Prof Antonio Molinaro Dr Yoshihiro Ueda Prof Cristina De Castro Prof Koichi Fukase |
| Institution: | 1. Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043 Japan
These authors contributed equally to this work.;2. Department of Agricultural Sciences, University of Napoli Federico II, Via Università 96, 80055 Portici, Naples, Italy These authors contributed equally to this work.;3. Department of Agricultural Sciences, University of Napoli Federico II, Via Università 96, 80055 Portici, Naples, Italy;4. Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043 Japan;5. Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510 Japan;6. Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043 Japan Department of Chemical Sciences, University of Napoli Federico II, Via Cintia 4, 80126 Napoli, Italy;7. Institute for Chemical Research, Kyoto University Gokasho, Uji, Kyoto, 611-0011 Japan |
| Abstract: | Asparagine-linked protein glycosylations (N-glycosylations) are one of the most abundant post-translational modifications and are essential for various biological phenomena. Herein, we describe the isolation, structural determination, and chemical synthesis of the N-glycan from the hyperthermophilic archaeon Thermococcus kodakarensis. The N-glycan from the organism possesses a unique structure including myo-inositol, which has not been found in previously characterized N-glycans. In this structure, myo-inositol is highly glycosylated and linked with a disaccharide unit through a phosphodiester. The straightforward synthesis of this glycan was accomplished through diastereoselective phosphorylation and phosphodiester construction by SN2 coupling. Considering the early divergence of hyperthermophilic organisms in evolution, this study can be expected to open the door to approaching the primitive function of glycan modification at the molecular level. |
| Keywords: | Archaea Glycosylation Inositol N-Glycans Structure Determination |