| 1. |
Keiya Uezono, Risa Maeda, Hiroaki Matoba, Makoto Yoritate, Go Hirai, Efficient synthetic method for C3-modified sialoglycans and their inhibitory activity for sialidases, Sialoglyco 2022, 2022.09. |
| 2. |
Risa Maeda, Keiya Uezono, Ryo Fukazawa, Hiroaki Matoba, Makoto Yoritate, Mikiko Sodeoka, Go Hirai, Sialylgalactose analogue with exomethylene group acts as a substrate but inhibits sialidase activity, Sialoglyco 2022, 2022.09. |
| 3. |
Takahiro Moriyama, Shunsuke Ono, Makoto Yoritate, Suzuka Chiba, Riko Tanabe, Go Hirai, Development of efficient synthesis method of carbohydrate analogues by direct C-glycosylation, 30th Interntional Carbohydrate Symposium, 2022.07. |
| 4. |
Makoto Yoritate, Hiroki Yasutomi, Daiki Takeda, Go Hirai, Transition-Metal-Free β-Selective C-Glycosylation of β-Glycosyl Boronate via Stereoretentive 1,2-Rearrangement, 30th Interntional Carbohydrate Symposium, 2022.07. |
| 5. |
Takahiro Ikazaki, Eri Ishikawa, Hisako Akiyama, Yusuke Kimuro, Makoto Yoritate, Sho Yamasaki, Go Hirai, Stereoselective Synthesis of Pseudo-Glycoconjugates with 2-Exomethylene Group and their biological activity, 30th Interntional Carbohydrate Symposium, 2022.07. |
| 6. |
Daiki Takeda, Hiroki Yasutomi, Suzuka Chiba, Makoto Yoritate, Go Hirai, α-Selective Direct C-Glycosylation with β-Glycosyl Trifluoroborates for Synthesis of 2-Deoxy-α-C-Glycosides, 30th Interntional Carbohydrate Symposium, 2022.07. |
| 7. |
Go Hirai, 3-Exomethylene sialic acid disaccharides as substrate-type sialidase inhibitors, Sialoglyco2022, 2022.09, Sialidases (neuraminidases) are a type of exo-glycoside hydrolases and catalyze trimming of a sialic acid residue from sialoglycans. Expression of sialidases is recognized in a variety of organisms, and several pathogenic bacterial or viral sialidases like the influenza virus are known to play a central role in their toxicity or lifecycles. In humans, NEU1~4 have also been identified, and their functions have gradually been clarified. Development of sialidase inhibitors, which would be necessary for further analysis of the precise function of sialidases as well as the development of therapeutic agents, have been surveyed. Almost all of them are regarded as analogues inspired by the transition state of the hydrolase reaction such as derivatives of DANA (1).
On the other hand, mechanism-based inhibitors (MBIs) are also useful molecular tools for functional analysis of sialidases, and compound 2 are representative MBIs. Although the inductive fluorine atom at C-3 position is important for stabilization of the sialidase-substrate complex, this fluorine atom also induces retardation of the cleavage of the O-sialoside linkage. Therefore, introduction of a leaving group (fluorine atom at C-2 position) is necessary to act as a substrate of sialidases, and current MBIs for sialidases (and also all exo-glycoside hydrolases) are limited to mono-saccharide analogues, to our knowledge.
We envisioned MBIs with disaccharide structures, which efficiently interacts with sialidases before cleavage, considering their substrate recognition ability. In this presentation, we report the disaccharide substrate analogues 3 or 4 acting as MBIs with a novel machinery for covalent bond formation.. |
| 8. |
平井 剛, Taking Our Chances with Potentials of pseudo-Glycans, 理化学研究所環境資源科学研究センター同窓ネットワーク第二回交流会, 2022.10. |
| 9. |
木谷憲昭、寄立麻琴、平井剛, 代謝耐性型ヒアルロナンオリゴマーの合成研究, 日本化学会第102春季年会, 2022.03. |
| 10. |
Go Hirai, Shunsuke Ono, Takahiro Moriyama, Makoto Yoritate, Synthesis and biological activity of C-linked glycan and glycolipid analogues, Pacifichem 2021: Middle molecular strategy for regulation of protein-protein & protein-biomolecule interactions (#370), 2021.12. |
| 11. |
Go Hirai, Ryo Fukazawa, Keiya Uezono, Kenta Mizui, Makoto Yoritate, Mikiko Sodeoka, Substrate-type Sialidase Inhibitors Involving Unique Mechanism-based Inhibition Machinery, Pacifichem 2021: Recent advances in carbohydrate chemistry and chemical glycobiology (#111), 2021.12. |
| 12. |
Takahiro Moriyama, Naoki Kato, Noriaki Kiya, Riko Tanabe, Makoto Yoritate, Minori Numamoto, Shunji Takahashi, Go Hirai, Unique Activity of C-isomaltose analogues in A. nidulans, AIMECS2121, 2021.11. |
| 13. |
Makoto Yoritate, Yuki Morita, Tomohiro Yamashita, Mikiko Sodeoka, and Go Hirai, Synthetic study and biological evaluation of DFGH-ring analogues of physalin-type natural products, AIMECS2121, 2021.11. |
| 14. |
Go Hirai, Efficient Synthetic Strategy for C-linked α-Galactosylceramide Analogues, 7th International Symposium on Middle Molecular Strategy (ISMMS-7)/ 16th Meeting of the International Endotoxin and Innate Immunit Society (IEIIS-16), 2021.10. |
| 15. |
Yoritate, M.; Morita, Y.; Morita, M; Yamashita, T.; Sodeoka, M.; Hirai, G., Development of New Synthetic Method of the DFGH-ring of Physalin-Type Natural Products and SAR Study of the Pseudo- Natural Products, 日本化学会第101春季年会, 2021.03. |
| 16. |
Go Hirai, Metabolically Stable Analogues and Photo-Reactive Probe for Understanding Glycolipid Functions, The 93rd Annual Meeting of the Japanese Biochemical Society: Toward understanding and control of sugar-containing lipids by biology and chemistry, 2020.09. |
| 17. |
Go Hirai, Glycan probes: C-glycosides and photo-affinity probes, ACGG11, 2019.11. |
| 18. |
Go Hirai, Synthesis and biological potential of carbohydrate analogues, 19th Tateshina Conference, 2019.11. |
| 19. |
Yuki Morita, Manuel Gemander, Masaki Morita, Mikiko Sodeoka, Go Hirai, Synthesis of Biologically Active Molecules Based on Unique Right-Side Structure of Physalins, 27th International Society of Heterocyclic Chemistry Congress, 2019.09. |
| 20. |
Noriaki kiya, Yu Hidaka, Makoto Yoritate, Kazuteru Usui, Go Hirai, Synthetic studies of 1,6-C-linked disaccharide analogues based on direct radical coupling, European Carbohydrate Symposium (EurocarboXX), 2019.07. |
| 21. |
Go Hirai, Thienyl‐substituted α‐ketoamide: a less hydrophobic photoreactive group useful for analysis of carbohydrate‐protein interaction, European Carbohydrate Symposium (EurocarboXX), 2019.07. |
| 22. |
Yu Mikame, Kazuko Yoshida, Go Hirai, Kazuo Nagasawa, Hiroyuki Osada, Mikiko Sodeoka, Structure activity relationship study of abscisic acid (ABA) receptor antagonist RK460, 日本化学会第99春季年会, 2019.03. |
| 23. |
Yuki Morita, Manuel Gemander, Masaki Morita, Mikiko Sodeoka, Go Hirai, Synthesis of biologically active molecules based on complex right-side structure of physalins, 第6回日英触媒的不斉合成シンポジウム, 2018.11. |
| 24. |
Noriaki kiya, Yu Hidaka, Kazuteru Usui, Go Hirai, Synthetic studies of 1,6-C-linked disaccharide analogues based on radical coupling, IKCOC-14, 2018.11. |
| 25. |
平井 剛, Thienyl-Substituted α-Ketoamide: a Less Hydrophobic Photoreactive Group, The Third A3 Roundtable Meeting on Chemical Probe Research Hub, 2018.11. |
| 26. |
Yuki Morita, Manuel Gemander, Masaki Morita, Mikiko Sodeoka, Go Hirai, Synthesis of Unique Right-Side Structure of Physalins, IRCCS-CREST Joint Symposium, 2018.01. |
| 27. |
Yu Hidaka, Noriaki Kiya, Kazuteru Usui, Go Hirai, Synthetic studies of C-linked disaccharide analogues based on radical coupling, IRCCS-CREST Joint Symposium, 2018.01. |
| 28. |
Masaki Morita, Go Hirai, Mikiko Sodeoka, Synthetic Strategy Towards Unique Right-Side Structures of Physalins, ISONIS-11 & ISMMS-3, 2017.11. |
| 29. |
Go Hirai, Synthesis of Natural Product Compartments for Finding Their Functions, The 3rd HU-TMU-KU Joint Symposium for Pharmaceutical Sciences, 2017.09. |
| 30. |
Go Hirai, Synthesis of Monomers for Spectomycin B1, A Middle Size SUMOylation Inhibitor Molecule, 7th CCS/CSJ Young Chemist Forum, 2017.03. |
| 31. |
Go Hirai, Synthesis of Monomers for Spectomycin B1, A Middle Size SUMOylation Inhibitor Molecule, 7th CCS/CSJ Young Chemist Forum（第7回日中若手化学者フォーラム）, 2017.03. |
| 32. |
深澤 亮, 大沼 可奈, 加藤 麻理依, 平井 剛, 袖岡 幹子, Development of the Disaccharide-Type Activity-Based Probe for Sialidase, 日本化学会第97春季年会, 2017.03. |
| 33. |
平井 剛, 三瓶 悠, 由田 和津子, 長澤 和夫, 長田 裕之, 袖岡 幹子, Synthesis of all the possible isomers of RK460 and its activity evaluation, 日本化学会第97春季年会, 2017.03. |
