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Faculty of Pharmaceutical Sciences Department of Pharmaceutical Sciences |
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YAMANOI Takashi
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Employment Record in Research 【 display / non-display 】
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Josai University Faculty of Pharmaceutical Sciences Department of Pharmaceutical Sciences Professor
2014.04
Papers 【 display / non-display 】
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α-Glucoside Formation from 2-Deoxy-2-(2,2,2-trichloroethoxycarboxamido)-α-D-glucopyranosyl Acetate Using an Activating System That Used a Combination of Ytterbium(III) Triflate and a Catalytic Boron Trifluoride Diethyl Etherate Complex Invited Reviewed
T. Yamanoi, Y. Oda, A. Koizumi, T. Kawaguchi, S. Yagihara, and A. Yoshida
Heterocycles 99 834 - 840 2019.04
Language：English Publishing type：Research paper (scientific journal) Publisher：日本複素環化学研究所
This study describes the formation of α-glucoside from 3,4,6-tri-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarboxamido)-α-D-glucopyranosyl acetate using an activating system that used a combination of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex. This glucoside formation using various types of alcohol acceptors proceeded with high α-stereoselectivity. The novel glucoside method employed in this study is a useful technique for producing 2-amino-2-deoxy-α-D-glucopyranoside derivatives because a 2,2,2-trichloroethoxycarbonyl group from an N-protecting group is easily removable.
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Use and Recyclability of Scandium Tris[bis(perfluorooctylsulfonyl)amide] As A Lewis Acid Promoter for Glycosidation Reactions Reviewed International journal
Takashi Yamanoi, Ryo Inoue, Yoshiki Oda, Akihiro Yoshida
Letters in Organic Chemistry 15 ( 12 ) 1050 - 1053 2018.12
Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：Bentham Science Publisher
In this study, the application of scandium tris[bis(perfluorooctylsulfonyl)amide] as a catalyst in glycosidation reactions was investigated. Besides being a versatile Lewis acid promoter for such reactions, the studied complex could be easily recovered from the reaction mixtures with sufficient activity to repeatedly catalyze the glycosidation reactions.
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A Synthetic Approach to Derive exo-Glucal Derivatives Through the Reaction of a1-C-Vinylated Glucopyranose Derivative with Phenols Invited Reviewed International journal
Takashi Yamanoi, Sho Matsuda, Junki Nakgawa, Mikio Watanabe, Yoshiki Oda, Akihiro Yoshida
Heterocycles 97 170 - 177 2018.09
Language：English Publishing type：Research paper (scientific journal) Publisher：日本複素環化学研究所
In this study, a synthetic approach to prepare exo-glucal derivatives through the reaction of a 1-C-vinylated glucopyranose derivative with phenols in the presence of an appropriate promoter has been investigated. The reaction between 2,3,4,6-tetra-O-benzyl-1-C-vinyl-α-D-glucopyranose and different phenols using 5 mol% Bi(OTf)3 produced the corresponding exo-glucal derivatives as major products along with spiro O-glucoside derivatives as minor products.
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Separation of the α- and β-Anomers of Carbohydrates by Diffusion-Ordered NMR Spectroscopy Invited Reviewed
T. Yamanoi, Y. Oda, K. Katsuraya
Magnetochemistry 3 38 - 43 2017.11
Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：MDPI
This article describes the successful application of the DOSY method for the separation and analysis of the α- and β-anomers of carbohydrates with different diffusion coefficients. In addition, the DOSY method was found to effectively separate two kinds of glucopyranosides with similar aglycon structures from a mixture.
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NMR Determination of concentration-switchable inclusion complex of a β-cyclodextrin derivative carrying a benzene group linked to a C,C-glucopyranoside spacer Reviewed
T. Yamanoi, Y. Oda, and K. Katsuraya
J. Incl. Phenom. Macrocycl. Chem. 89 189 - 197 2017.10
Authorship：Lead author Language：English Publishing type：Research paper (scientific journal) Publisher：Springer
This article describes the structure of the inclusion complex that a β-cyclodextrin derivative 1, which includes a benzene ring tethered to a cyclodextrin moiety via a C,C-glucopyranoside spacer, forms when its concentration is 9 mM. As we have recently reported, 1 forms an intramolecular inclusion complex at a concentration of 2 mM. By contrast, detailed NMR structural analysis revealed that at a 9 mM concentration, 1 formed a symmetrical pseudo-dimer based on intermolecular inclusion complexiation between two molecules of 1. Thus, the inclusion structures of 1 varied depending on concentration, which indicates that the structure of this β-cyclodextrin derivative could be “concentration-switchable.”
Misc 【 display / non-display 】
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Stereoselectivity of D-psicofuranosylation reactions catalyzed by scandium triflate Reviewed
T. Yamanoi, T. Ishiyama, and M. Watanabe
Proceedings of the Fifth Symposium of International Society of Rare Sugars 29 - 33 2011
Authorship：Lead author Language：English Publishing type：Article, review, commentary, editorial, etc. (international conference proceedings)
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Reactions and uses of artificial ketoses Invited Reviewed
T. Yamanoi and S. Matsuda
Heterocycles 79 163 - 194 2009
Authorship：Lead author Language：English Publishing type：Article, review, commentary, editorial, etc. (scientific journal)
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Synthetic approach from D-mannose to 2,7-anhydro-D-sedoheptulose Reviewed
S. Matsuda and T. Yamanoi
Proceedings of the Fourth Symposium of International Society of Rare Sugars 84 - 88 2008
Language：English Publishing type：Article, review, commentary, editorial, etc. (international conference proceedings)
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Glycosidation of the rare sugars, L-fructose and D-psicose Reviewed
T. Ishiyama, T. Yamanoi, and M. Watanabe
Proceedings of the Fourth Symposium of International Society of Rare Sugars 76 - 80 2008
Language：English Publishing type：Article, review, commentary, editorial, etc. (international conference proceedings)
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H and 13C DOSY spectra of the mixed sample of α-cyclodextrin and phenyl alpha-D-(13C6)glucopyranoside Reviewed
Y. Oda, S. Matsuda, T. Yamanoi, A. Murota, and K. Katsuraya
Proceeding of the 14th International Symposium on Cyclodextrins 417 - 420 2008
Authorship：Lead author Language：English Publishing type：Article, review, commentary, editorial, etc. (international conference proceedings)
Presentations 【 display / non-display 】
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シクロデキストリンによるドキソルビシン会合構造体のＮＭＲ解析
鬘谷 要, 小田慶喜, 山ノ井孝
第35回シクロデキストリンシンポジウム 日本シクロデキストリン学会
Event date： 2018.09
Language：Japanese Presentation type：Poster presentation
Venue：甲府
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糖鎖抗原を用いた迅速な多包虫症診断法の開発
小泉 晶彦、安保 秀美、山ノ井 孝
第37回糖質学会
Event date： 2018.08
Language：Japanese Presentation type：Poster presentation
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Synthesis of β-cyclodextrin derivatives multivalently conjugated with carbohydrate moieties through click chemistry reaction International conference
Y. Oda, J. Nakagawa, M. Watanabe, T. Yamanoi
The 19th International Cyclodextrin Symposium
Event date： 2018.04
Language：English Presentation type：Poster presentation
Venue：東京
The cyclodextrins (CyDs) play a functional role as scaffold molecules for enabling to conjugate organic compounds to CyDs via co-valent bonds. The structural feature of CyDs usefully leads to the development of CyD-based functional materials. In CyD chemistry, it is currently one of the most significant subjects to develop the scaffold use of CyD molecules. The CyD derivatives with multivalent carbohydrate ligands are expected to be drug carriers. Therefore, this study describes the design and synthesis of newly several β-CyD derivatives multivalently conjugated with carbohydrate moieties through click chemistry reaction.
Scheme 1 presents the synthetic approch for the β-CyD derivative 3 conjugated with seven glucopyranose moieties from β-CyD and β-arbutin (natural product, p-hydroxyphenyl β-D-glucopyranoside). The azide-alkyne Huisgen cycloaddition between the acetylated β-arbutin derivative 1 with a propargyl group and the acetylated hepta(6-azido-6-deoxy)-β-CyD derivative 2 using CuSO4 and sodium ascorbate in THF / H2O (1 / 1) was smoothly promoted by microwave irradation to afforded the precursor, acetyl protected β-CyD derivative. The following deacetylation of 3 gave the desired β-CyD derivative 3 in good yield.
Several types of β-CyD derivatives with seven carbohydrate moieties from α-arbutin (p-hydroxyphenyl α-D-glucopyranoside), mannopyranose (Man) or 2-acetoamido-2-deoxy-glucopyranose (GlcNAc), were also sucessfully demonstrated. Furthermore, we investigated the synthesis of hybride types of β-CyD derivatives multivalently with mixed carbohydrates moieties (β-arbutin, α-arbutin, Man, and GlcNAc). -
インフルエンザウイルス捕獲機能を有する糖鎖多分岐シクロデキストリン誘導体の合成研究 International conference
山ノ井孝、小田慶喜、苫米地祐輔、中川純樹、渡邊幹夫、山本憲二
第34回シクロデキストリンシンポジウム シクロデキストリン学会
Event date： 2017.08 - 2017.09
Language：Japanese Presentation type：Oral presentation (general)
Venue：名古屋
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Endo-M酵素を用いたグルコース七残基分岐β-CyDへのN-結合型糖 鎖の集積化
苫米地 祐輔, 中川 純樹, 渡邊 幹夫, 小田 慶喜, 山本 憲二, 山ノ 井 孝
第36回日本糖質学会年会 日本糖質学会
Event date： 2017.07
Language：Japanese Presentation type：Poster presentation
Venue：旭川
Committee Memberships 【 display / non-display 】
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東京糖鎖研究会 幹事会員
2016.04
Committee type：Academic society
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日本糖質学会 評議員
2003.07
Committee type：Academic society
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シクロデキストリン学会 評議員
2003.04
Committee type：Academic society