Structural Determination and Chemical Synthesis of the N‐Glycan from the Hyperthermophilic Archaeon Thermococcus kodakarensis. Issue 13 (16th February 2023)

• Record Type: Journal Article
• Authors: Hirao, Kohtaro; Speciale, Immacolata; Notaro, Anna; Manabe, Yoshiyuki; Teramoto, Yoshiaki; Sato, Takaaki; Atomi, Haruyuki; Molinaro, Antonio; Ueda, Yoshihiro; De Castro, Cristina; Fukase, Koichi
• Is Part Of: Angewandte Chemie international edition. Volume 62:Issue 13(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-02-16
• Subjects: Archaea -- Glycosylation -- Inositol -- N-Glycans -- Structure Determination; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202218655
• Languages: English
• ISSNs: 1433-7851

Abstract

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 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. Abstract : The isolation, structural determination, and chemical synthesis of an N ‐glycan from the hyper‐thermophilic archaeon Thermococcus kodakarensis are reported. The identified N ‐glycan possesses a highly glycosylated myo ‐inositol moiety, which is linked to a disaccharide unit through a phosphodiester. Although myo ‐inositol is ubiquitous in archaea and eukaryotes, inositol‐containing N ‐glycans were unknown until now.