Kyushu University Academic Staff Educational and Research Activities Database
List of Papers
Yoritate Makoto Last modified date:2024.06.03

Assistant Professor / Go Hirai Group / Department of Chemo-Pharmaceutical Sciences / Faculty of Pharmaceutical Sciences


Papers
1. isuke 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, 40, 333-341, 2023.03, [URL], 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. Taishi Miura, Makoto Yoritate, Go Hirai, Photoredox-catalyzed protecting-group-free C-glycosylation with glycosyl sulfinate via the Giese reaction, Chemical Communications (Cambridge, England), 10.1039/d3cc02361c, 59, 8564-8567, 2023.06, [URL], C-Glycoside analogs of naturally occurring glycoconjugates are useful tools for chemical biology studies, but their synthesis usually requires protection of the hydroxyl groups of the glycosyl donors. Here we report protecting-group-free and photoredox-catalyzed C-glycosylation with glycosyl sulfinates and Michael acceptors via the Giese radical addition..
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 Activities of 2-Exomethylene Pseudo-glycoconjugates: Discovery of Mincle-Selective Ligands., Angewandte Chemie (International ed. in English), 10.1002/anie.202302569, e202302569, 2023.04, Glycoconjugate analogues in which the sp3-hybridized C2 position of the carbohydrate structure (normally bearing a hydroxyl group) is converted to a compact sp2-hybridized exo-methylene group are expected to have unique biological activities. We established ligand-controlled Tsuji-Trost-type glycosylation methodology to directly prepare a variety of these 2-exo-methylene pseudo-glycoconjugates, including glucosylceramide analogues, in an α- or β-selective manner. Glucocerebrosidase GBA1 cleaves these synthetic pseudo-β-glucosylceramides similarly to native glucosylceramides. The pseudo-glucosylceramides exhibit selective ligand activity towards macrophage-inducible C-type lectin (Mincle), but unlike native glucosylceramides, are inactive towards CD1d..
4. Yasukazu Sugiyama, Yasuki Soda, Makoto Yoritate, Hayato Tajima, Yoshito Takahashi, Kana Shibuya, Chisato Ogihara, Takashi Yokoyama, Takeshi Oishi, Takaaki Sato, Noritaka Chida, Lactam Strategy Using Amide-Selective Nucleophilic Addition for Quick Access to Complex Amines: Unified Total Synthesis of Stemoamide-Type Alkaloids, Bulletin of the Chemical Society of Japan, 10.1246/bcsj.20210372, 95, 2, 278-287, 2022.02.
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6. Yu Hidaka, Noriaki Kiya, Makoto Yoritate, Kazuteru Usui, Go Hirai, Synthesis of CH2-linked α-galactosylceramide and its glucose analogues through glycosyl radical-mediated direct C-glycosylation., Chemical communications (Cambridge, England), 10.1039/d0cc00785d, 56, 34, 4712-4715, 2020.03, We describe a new synthetic approach for C-linked glycolipid analogues, in which the cleavable O-glycosidic linkage is replaced by a carbon unit. Direct C-glycosylation of a conformationally constrained and stable C1-sp3 hybridized xanthate carbohydrate with carefully designed sphingosine units afforded the CH2-linked analogue of antitumor-active KRN7000 and its glucose congener..
7. Makoto Yoritate, Allyn T. Londregan, Yajing Lian, John F. Hartwig, Sequential Xanthalation and O-Trifluoromethylation of Phenols
A Procedure for the Synthesis of Aryl Trifluoromethyl Ethers, Journal of Organic Chemistry, 10.1021/acs.joc.9b02717, 84, 24, 15767-15776, 2019.12.
8. Álvaro Velasco-Rubio, Eric J. Alexy, Makoto Yoritate, Austin C. Wright, Brian M. Stoltz, Stereospecific Overman Rearrangement of Substituted Cyclic Vinyl Bromides
Access to Fully Substituted α-Amino Ketones, Organic letters, 10.1021/acs.orglett.9b03347, 21, 22, 8962-8965, 2019.11, A versatile thermal Overman rearrangement of enantioenriched, cyclic allylic alcohols providing tertiary allylic amines has been developed. The vinyl bromide used to control enantioselectivity in a preceding CBS reduction is utilized as a synthetic handle for the preparation of tertiary α-amino ketones and related derivatives in an asymmetric fashion..
9. Takeshi Oishi, Makoto Yoritate, Takaaki Sato, Noritaka Chida, Crystal structure of (-)-(5R,7R,8S,9R,10S)-8-methyl-7-[(5 R)-3-methyl-2-oxooxolan-3-en-5-yl]-1-aza-6-oxatricyclo[8.3.0.0 5,9 ]tridecan-13-one monohydrate, Acta Crystallographica Section E: Crystallographic Communications, 10.1107/S2056989018004425, 74, 555-558, 2018.04, The title compound, C17 H23 NO4 ·H2 O, is an epimer of the natural tetracyclic alkaloid isosaxorumamide which consists of a fused 5-7-5 tricyclic core and a dihydrofuranone substituent. The terminal dihydrofuran ring is essentially planar with a maximum deviation of 0.0273(14)Å from the mean plane and oxolane, azepane and pyrrolidine rings in the tricyclic ring system adopt twist, twist-chair and envelope forms, respectively. In the crystal, the amide and water molecules are linked by O - H...O hydrogen bonds, forming a tape structure running along the b-axis direction. The tapes are further connected by C - H...O interactions into a three-dimensional architecture..
10. Takaaki Sato, Makoto Yoritate, Hayato Tajima, Noritaka Chida, Total synthesis of complex alkaloids by nucleophilic addition to amides, Organic and Biomolecular Chemistry, 10.1039/c8ob00733k, 16, 21, 3864-3875, 2018.01, Nucleophilic addition to amides has been recognized as a promising transformation for total synthesis of complex alkaloids. Amides can accept two different organometallic reagents through the nucleophilic addition, which enables it to serve as a stable surrogate of multi-substituted amines. However, the nucleophilic addition has been overlooked for a long time due to three main reasons: low electrophilicity of amide carbonyls, potential hydrolysis of the reaction intermediate and excess addition of an organometallic reagent. This mini review focuses on the recent progress of total synthesis of complex alkaloids based on the nucleophilic additions to N-alkoxyamides, tertiary amides and secondary amides..
11. Makoto Yoritate, Yoshito Takahashi, Hayato Tajima, Chisato Ogihara, Takashi Yokoyama, Yasuki Soda, Takeshi Oishi, Takaaki Sato, Noritaka Chida, Unified Total Synthesis of Stemoamide-Type Alkaloids by Chemoselective Assembly of Five-Membered Building Blocks, Journal of the American Chemical Society, 10.1021/jacs.7b10944, 139, 50, 18386-18391, 2017.12.
12. Kenji Shirokane, Yuya Tanaka, Makoto Yoritate, Nobuaki Takayama, Takaaki Sato, Noritaka Chida, Total syntheses of (±)-gephyrotoxin and (±)-perhydrogephyrotoxin, Bulletin of the Chemical Society of Japan, 10.1246/bcsj.20140398, 88, 4, 522-537, 2015.01, This article describes the full details of our total syntheses of gephyrotoxin and perhydrogephyrotoxin. Our central strategy toward the total synthesis is based on the use of an N-methoxy group as a reactivity control element. The N-methoxyamide group enabled unique transformations, involving i) the direct coupling reaction of the N-methoxyamide with an aldehyde, and ii) the amide-selective reductive allylation. These reactions were never accomplished without the assistance of the N-methoxy group. The amide-selective reductive allylation of the N-methoxyamide was especially practical, and excluded a number of extra steps including protecting group manipulations and redox reactions in the total syntheses..
13. Takeshi Oishi, Makoto Yoritate, Takaaki Sato, Noritaka Chida, (5R*)-5-[(2S*5S*)-1-Methoxy-5-phenylpyrrolidin-2-yl] -3-methylfuran-2(5H)-one, Acta Crystallographica Section E: Structure Reports Online, 10.1107/S1600536814014974, 70, 8, o839, 2014.08, In the title compound, C16H19NO3, the pyrrolidine ring is in a twist conformation. The dihedral angle between the dihydrofuran ring [maximum deviation = 0.0016(11)Å] and the phenyl ring is 47.22(8)°. In the crystal, molecules are linked by weak C - H⋯O hydrogen bonds, forming helical chains along the b-axis direction. The chains are further linked by C - H⋯π interactions to constitute a three-dimensional architecture..
14. Makoto Yoritate, Tatsuhiko Meguro, Naoya Matsuo, Kenji Shirokane, Takaaki Sato, Noritaka Chida, Two-step synthesis of multi-substituted amines by using an N-methoxy group as a reactivity control element, Chemistry - A European Journal, 10.1002/chem.201402231, 20, 26, 8210-8216, 2014.06.
15. Kenji Shirokane, Takamasa Wada, Makoto Yoritate, Ryo Minamikawa, Nobuaki Takayama, Takaaki Sato, Noritaka Chida, Total synthesis of (±)-gephyrotoxin by amide-selective reductive nucleophilic addition, Angewandte Chemie - International Edition, 10.1002/anie.201308905, 53, 2, 512-516, 2014.01, A chemoselective approach for the total synthesis of (±)- gephyrotoxin has been developed. The key to success was the utilization of N-methoxyamides, which enabled the direct coupling of the amide with an aldehyde and selective reductive nucleophilic addition to the amide in the presence of a variety of sensitive and electrophilic functional groups, such as a methyl ester. This chemoselective approach minimized the use of protecting-group manipulations and redox reactions, which resulted in the most concise and efficient total synthesis of (±)-gephyrotoxin described to date. Aim for selectivity: A chemoselective approach that utilizes N-methoxyamides has been developed for the total synthesis of (±)-gephyrotoxin. The N-methoxy group enabled the direct coupling of the amide with an aldehyde and amide-selective reductive allylation in the presence of a more electrophilic methyl ester, which resulted in the most concise and efficient total synthesis of (±)-gephyrotoxin described to date..