Structural Determination and Chemical Synthesis of the N-Glycan from the Hyperthermophilic Archaeon Thermococcus kodakarensis.

Kohtaro Hirao, Immacolata Speciale, Anna Notaro, Yoshiyuki Manabe, Yoshiaki Teramoto, Takaaki Sato, Haruyuki Atomi, Antonio Molinaro, Yoshihiro Ueda, Cristina De Castro, Koichi Fukase

Angewandte Chemie (International ed. in English) 2023 Mar 20

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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 SN 2 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. © 2023 Wiley-VCH GmbH.

Citation

Kohtaro Hirao, Immacolata Speciale, Anna Notaro, Yoshiyuki Manabe, Yoshiaki Teramoto, Takaaki Sato, Haruyuki Atomi, Antonio Molinaro, Yoshihiro Ueda, Cristina De Castro, Koichi Fukase. Structural Determination and Chemical Synthesis of the N-Glycan from the Hyperthermophilic Archaeon Thermococcus kodakarensis. Angewandte Chemie (International ed. in English). 2023 Mar 20;62(13):e202218655