Papers - Tsutsui, Masato

Validation and Application of an Innovative Protective Group Concept: Enhancing Substrate Reactivity in Glycosylations by Disrupting Intermolecular Interactions

Kumpei Yano, Takuya Yoshimoto, Masato Tsutsui, Yoshiyuki Manabe, Koichi Fukase

Synlett (Georg Thieme Verlag KG)  35 2024.02

Accepted,  ISSN  0936-5214

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Abstract

We have established an innovative protective approach that disrupts intermolecular interactions to enhance substrate reactivity. Specifically, diacetylimide protection of acetamide prevents the formation of hydrogen bonds, while the incorporation of tert-butyl groups on the aromatic protecting group disrupts π-stacking interactions, both of which culminate in heightened reactivity in glycosylations. We explored the synergistic implementation of these protective measures and applied them to the synthesis of 6-sulfo sialyl Lewis X.

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Practical Antibody Recruiting by Metabolic Labeling with Caged Glycans.

Hersa Milawati, Yoshiyuki Manabe, Takuya Matsumoto, Masato Tsutsui, Yoshihiro Ueda, Ayane Miura, Kazuya Kabayama, Koichi Fukase

Angewandte Chemie (International ed. in English)    e202303750 2023.04

Accepted

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We propose a de novo glycan display that combines metabolic labeling and a glycan-caging strategy as a facile editing method for cell-surface glycans. This method enables the introduction of antigen glycans onto cancer cells to induce immune responses through antibody recruiting. The caging strategy prevents the capture of α-rhamnose (an antigen glycan) by their endogenous antibodies during the introduction of the glycan to the targeted cell surface, and subsequent uncaging successfully induces immune responses. Therefore, this study proposes a practical method for editing the cell-surface glycocalyx under promiscuous conditions, such as those in vivo, which paves the way for the development of glycan function analysis and regulation.

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Mechanistic Studies for the Rational Design of Multivalent Glycodendrimers

Yoshiyuki Manabe, Masato Tsutsui, Kohtaro Hirao, Risako Kobayashi, Hiroshi Inaba, Kazunori Matsuura, Daisuke Yoshidome, Kazuya Kabayama, Koichi Fukase

Chemistry – A European Journal (Wiley)   2022.07

Accepted,  ISSN  0947-6539

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Synthesis of ABO blood group antigens and functional glycan display on the cell surface

Masato Tsutsui, Yoshiyuki Manabe, Kazuya Kabayama, Koichi Fukase

Arkivoc (ARKAT USA, Inc.)  2021 ( 4 ) 168 - 185 2020.11

Lead author, Accepted

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Concise and Reliable Syntheses of Glycodendrimers via Self-Activating Click Chemistry: A Robust Strategy for Mimicking Multivalent Glycan-Pathogen Interactions.

Kindi Farabi, Yoshiyuki Manabe, Hiroaki Ichikawa, Shuto Miyake, Masato Tsutsui, Kazuya Kabayama, Toshiyuki Yamaji, Katsunori Tanaka, Shang-Cheng Hung, Koichi Fukase

The Journal of organic chemistry 85 ( 24 ) 16014 - 16023 2020.10

Accepted

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Individual interactions between glycans and their receptors are usually weak, although these weak interactions can combine to realize a strong interaction (multivalency). Such multivalency plays a crucial role in the recognition of host cells by pathogens. Glycodendrimers are useful materials for the reconstruction of this multivalent interaction. However, the introduction of a large number of glycans to a dendrimer core is fraught with difficulties. We herein synthesized antipathogenic glycodendrimers using the self-activating click chemistry (SACC) method developed by our group. The excellent reactivity of SACC enabled the efficient preparation of sialyl glycan and Gb3 glycan dendrimers, which exhibited strong avidity toward hemagglutinin on influenza virus and Shiga toxin B subunit produced by Escherichia coli, respectively. We demonstrated the usefulness of SACC-based glycodendrimers as antipathogenic compounds.

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Efficient Synthesis of Antigenic Trisaccharides ContainingN-Acetylglucosamine: Protection of NHAc as NAc2

Masato Tsutsui, Julinton Sianturi, Seiji Masui, Kento Tokunaga, Yoshiyuki Manabe, Koichi Fukase

European Journal of Organic Chemistry (Wiley)  2020 ( 12 ) 1802 - 1810 2020.03

Lead author, Accepted,  ISSN  1434-193X

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Front Cover: Efficient Synthesis of Antigenic Trisaccharides Containing N-Acetylglucosamine: Protection of NHAc as NAc2 (Eur. J. Org. Chem. 12/2020)

Masato Tsutsui, Julinton Sianturi, Seiji Masui, Kento Tokunaga, Yoshiyuki Manabe, Koichi Fukase

European Journal of Organic Chemistry (Wiley)  2020 ( 12 ) 1782 - 1782 2020.03

Lead author,  ISSN  1434-193X

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