山ノ井 孝 (ヤマノイ タカシ)

YAMANOI Takashi

写真a

職名

教授

研究分野・キーワード

有機合成化学、糖質科学、分子認識

学内職務経歴 【 表示 / 非表示

  • 2014年04月
    -
    継続中

    城西大学   薬学部   薬学科   教授  

 

論文 【 表示 / 非表示

  • 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

    T. Yamanoi, Y. Oda, A. Koizumi, T. Kawaguchi, S. Yagihara, and A. Yoshida

    Heterocycles ( 日本複素環化学研究所 )  99   834 - 840   2019年04月  [査読有り]  [招待有り]

    共著

    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.

    DOI

  • Use and Recyclability of Scandium Tris[bis(perfluorooctylsulfonyl)amide] As A Lewis Acid Promoter for Glycosidation Reactions

    Takashi Yamanoi, Ryo Inoue, Yoshiki Oda, Akihiro Yoshida

    Letters in Organic Chemistry ( Bentham Science Publisher )  15 ( 12 ) 1050 - 1053   2018年12月  [査読有り]

    共著

    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.

    DOI

  • A Synthetic Approach to Derive exo-Glucal Derivatives Through the Reaction of a1-C-Vinylated Glucopyranose Derivative with Phenols

    Takashi Yamanoi, Sho Matsuda, Junki Nakgawa, Mikio Watanabe, Yoshiki Oda, Akihiro Yoshida

    Heterocycles ( 日本複素環化学研究所 )  97   170 - 177   2018年09月  [査読有り]  [招待有り]

    共著

    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.

    DOI

  • Separation of the α- and β-Anomers of Carbohydrates by Diffusion-Ordered NMR Spectroscopy

    T. Yamanoi, Y. Oda, K. Katsuraya

    Magnetochemistry ( MDPI )  3   38 - 43   2017年11月  [査読有り]  [招待有り]

    共著

    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.

    DOI

  • NMR Determination of concentration-switchable inclusion complex of a β-cyclodextrin derivative carrying a benzene group linked to a C,C-glucopyranoside spacer

    T. Yamanoi, Y. Oda, and K. Katsuraya

    J. Incl. Phenom. Macrocycl. Chem. ( Springer )  89   189 - 197   2017年10月  [査読有り]

    共著

    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.”

全件表示 >>

総説・解説記事 【 表示 / 非表示

  • Stereoselectivity of D-psicofuranosylation reactions catalyzed by scandium triflate

    T. Yamanoi, T. Ishiyama, and M. Watanabe

    Proceedings of the Fifth Symposium of International Society of Rare Sugars     29 - 33   2011年  [査読有り]

    総説・解説(国際会議プロシーディングズ)   共著

  • Reactions and uses of artificial ketoses

    T. Yamanoi and S. Matsuda

    Heterocycles   79   163 - 194   2009年  [査読有り]  [依頼有り]

    総説・解説(学術雑誌)   共著

  • H and 13C DOSY spectra of the mixed sample of α-cyclodextrin and phenyl alpha-D-(13C6)glucopyranoside

    Y. Oda, S. Matsuda, T. Yamanoi, A. Murota, and K. Katsuraya

    Proceeding of the 14th International Symposium on Cyclodextrins     417 - 420   2008年  [査読有り]

    総説・解説(国際会議プロシーディングズ)   共著

  • Synthetic approach from D-mannose to 2,7-anhydro-D-sedoheptulose

    S. Matsuda and T. Yamanoi

    Proceedings of the Fourth Symposium of International Society of Rare Sugars     84 - 88   2008年  [査読有り]

    総説・解説(国際会議プロシーディングズ)   共著

  • Glycosidation of the rare sugars, L-fructose and D-psicose

    T. Ishiyama, T. Yamanoi, and M. Watanabe

    Proceedings of the Fourth Symposium of International Society of Rare Sugars     76 - 80   2008年  [査読有り]

    総説・解説(国際会議プロシーディングズ)   共著

全件表示 >>

研究発表 【 表示 / 非表示

  • 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  (甲府)  2018年09月  -  2018年09月    日本シクロデキストリン学会

  • 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  2018年08月  -  2018年08月   

  • Synthesis of β-cyclodextrin derivatives multivalently conjugated with carbohydrate moieties through click chemistry reaction

    Y. Oda, J. Nakagawa, M. Watanabe, T. Yamanoi

    The 19th International Cyclodextrin Symposium  (東京)  2018年04月  -  2018年04月   

    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

    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  (名古屋)  2017年08月  -  2017年09月    シクロデキストリン学会

  • 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  (旭川)  2017年07月  -  2017年07月    日本糖質学会

全件表示 >>

 

その他教育活動及び特記事項 【 表示 / 非表示

  • 2019年04月
    -
    継続中

    卒業研究評価

  • 2014年04月
    -
    継続中

    授業評価の対応

  • 2014年04月
    -
    継続中

    授業方法の工夫

 

学会・委員会等活動 【 表示 / 非表示

  • 2016年04月
    -
    継続中

    東京糖鎖研究会   幹事会員

  • 2003年07月
    -
    継続中

    日本糖質学会   評議員

  • 2003年04月
    -
    継続中

    シクロデキストリン学会   評議員