| 1. |
Go Hirai, Glycolipids, Methods in Molecular Biology (MIMB, volume 2613), Sialidase-Resistant Ganglioside GM3 Analogues: Evaluation of Biological Activity, Springer Nature Singapore Pte Ltd., 10.1007/978-1-0716-2910-9_7, 2023.01, Glycolipids play important biological roles mainly in biological membranes, but their functions at the molecular level remain to be fully established. A chemical biology approach using exogenously added glycolipid probes would be promising, but the possibility of cleavage by cellular glycohydrolases complicates the interpretation of results. Thus, there is a need for non-hydolyzable analogues. In the present study, we designed and synthesized GM3 analogues resistant to GM3-degrading sialidase by replacing the O-sialoside linkage with a C-sialoside linkage. The bioactivity of the analogues was also investigated.. |
| 2. |
Go Hirai, Advances in Carbohydrate Chemistry and Biochemistry, Special Volume in Memory of Hidetoshi Yamada Part 2, Chapter Three - Pseudo-glycoconjugates with a C-glycoside linkage, ELSEVIER, 10.1016/bs.accb.2022.10.002, 2022.12, Work by the author and colleagues has been focused on the development of pseudo-glycans (pseudo-glycoconjugates), in which the O-glycosidic linkage of the natural-type glycan structure is replaced by a C-glycosidic linkage. These analogues are not degraded by cellular glycoside hydrolases, and are thus expected to be useful molecular tools that may maintain the original biological activity for a long period in the cell. However, their biological potential is not yet well understood because only a few pseudo-glycans have so far been synthesized. This article aims to provide a bird's-eye view of our recent studies on the creation of C-glycoside analogues of ganglioside GM3 based on the CHF-sialoside linkage, and summarizes the chemical insights acquired during our stereoselective synthesis of the C-sialoside bond, ultimately leading to pseudo-GM3. Conformational analysis of the synthesized CHF-sialoside disaccharides confirmed that the anticipated conformational control by F-atom introduction was successful, and furthermore, enhanced the biological activity. In order to improve access to C-glycoside analogues based on pseudo-GM3, it is still important to streamline the synthesis process. With this in mind, we designed and developed a direct C-glycosylation method using atom-transfer radical coupling, and employed it in syntheses of pseudo-isomaltose and pseudo-KRN7000.. |
| 3. |
平井剛, 日本化学会 編：生体分子反応を制御する （CSカレントレビュー 36）： 化学的手法による機構と反応場の解明, 化学同人, 研究最前線 第16章 複合糖質の反応場を探る：代謝耐性型アナログと光親和性標識法（p145-152）, 2020.04. |
| 4. |
Go Hirai (Editors: Taniguchi, N., Endo, T., Hirabayashi, J., Nishihara, S., Kadomatsu, K., Akiyoshi, K., Aoki-Kinoshita, K.F.), Glycoscience: Basic Science to Applications, Springer Nature Singapore Pte Ltd., 10.1007/978-981-13-5856-2, 52-53, 2020.07. |
| 5. |
平井 剛, 未来を創るグライコサイエンス-我が国のロードマップ- 3-22 ラベル化糖鎖を用いた診断とイメージング, 日本糖鎖科学コンソーシアム（JCGG）編, 2018.05. |
| 6. |
袖岡幹子、平井剛, ケミカルバイオロジー化合物集 研究展開のヒント 第4章4.2 ホスファターゼ阻害剤, オーム社, 2018.10. |
| 7. |
平井剛、袖岡幹子, 天然有機化合物の全合成:独創的なものづくりの反応と戦略 (CSJカレントレビュー)
第14章研究最前線 ケミカルバイオロジーを志向した天然物アナログの創製：部分構造アナログと代謝安定型アナログ, 化学同人, 2018.03. |
| 8. |
平井剛, 天然有機化合物の全合成:独創的なものづくりの反応と戦略 (CSJカレントレビュー)
第4章天然物全合成の基礎 Basic Concept-5 全合成とケミカルバイオロジー, 化学同人, 2018.03. |
