| 1. |
Eisuke Ota, Daiki Takeda, Kana Oonuma, Marie Kato, Hiroaki Matoba, Makoto Yoritate, Mikiko Sodeoka, Go Hirai, Synthesis and biological activity of ganglioside GM3 analogues with a (S)-CHF-Sialoside linkage and an alkyne tag, Glycoconjugate Journal, 10.1007/s10719-023-10111-0, 2023.03, The alkyne tag, consisting of only two carbons, is widely used as a bioorthogonal functional group due to its compactness and nonpolar structure, and various probes consisting of lipids bearing an alkyne tag have been developed. Here, we designed and synthesized analogues of ganglioside GM3 bearing an alkyne tag in the fatty acid moiety and evaluated the effect of the alkyne tag on the biological activity. To eliminate the influence of other factors such as degradation of the glycan chain when evaluating biological activity in a cellular environment, we introduced the tag into sialidase-resistant (S)-CHF-linked GM3 analogues developed by our group. The designed analogues were efficiently synthesized by tuning the protecting group of the glucosylsphingosine acceptor. The growth-promoting effect of these analogues on Had-1 cells was dramatically altered depending upon the position of the alkyne tag.. |
| 2. |
Keiya Uezono, Risa Maeda, Makoto Yoritate, Hiroaki Matoba, Go Hirai, Modification of the C3-Position of 2,3-Dehydro-2-deoxy-N-acetylneuraminic Acid with An Acetic Acid Equivalent, Chemistry Letters, 10.1246/cl.220507, 52, 2, 71-74, 2023.02.  |
| 3. |
Takahiro Ikazaki, Eri Ishikawa, Hiroto Tamashima, Hisako Akiyama, Yusuke Kimuro, Makoto Yoritate, Hiroaki Matoba, Akihiro Imamura, Hideharu Ishida, Sho Yamasaki, Go Hirai, Ligand‐Controlled Stereoselective Synthesis and Biological Activity of 2‐Exomethylene Pseudo‐glycoconjugates: Discovery of Mincle‐Selective Ligands, Angewandte Chemie International Edition, 10.1002/anie.202302569, 62, 22, 2023.05. |
| 4. |
Amaechi Shedrack Odoh, Louise Aidanpaa, Nariyoshi Umekubo, Hiroaki Matoba, Naoki Mori, Yujiro Hayashi, Asymmetric Synthesis of Pentasubstituted Cyclohexanes through Diphenylprolinol Silyl Ether Mediated Domino Michael/Michael Reaction, European Journal of Organic Chemistry, org/10.1002/ejoc.202101106, 6670-6673, 2021.10. |
| 5. |
Hiroaki Matoba, Takahiro Watanabe, MasanoriNagatomo, Masayuki Inoue, Convergent Synthesis of Taxol Skeleton via Decarbonylative Radical Coupling Reaction, Organic Letters, 10.1021/acs.orglett.8b03302, 20, 23, 7554-7557, 2018.11. |
| 6. |
Tomoya Yamashita, Hiroaki Matoba, Takefumi Kuranaga, Masayuki Inoue, Total syntheses of nobilamides B and D: application of traceless Staudinger ligation, Tetrahedron, doi.org/10.1016/j.tet.2014.05.091, 70, 42, 7746-7752, 2014.06. |
