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＜journal article＞
Ligand-Controlled Stereoselective Synthesis and Biological Activity of 2-Exomethylene Pseudo-glycoconjugates: Discovery of Mincle-Selective Ligands

Other Titles
Ligand-controlled Stereoselective Synthesis and Biological Activities of 2-Exomethylene Pseudo-glycoconjugates: Discovery of Mincle-Selective Ligands
Creator
Creator Name
Ikazaki, Takahiro
伊ケ崎, 孝洋
イカザキ, タカヒロ
Affiliation
Affiliation Name
Graduate School of Pharmaceutical Science, Kyushu University
九州大学大学院薬学府創薬科学専攻
Author PID
20546478
Creator Name
Ishikawa, Eri
石川, 絵里
イシカワ, エリ
Affiliation
Affiliation Name
Department of Molecular Immunology Research Institute for Microbial Diseases, Osaka University
大阪大学微生物病研究所
Affiliation
Affiliation Name
Laboratory of Molecular Immunology Immunology Frontier Research Center, Osaka University
大阪大学免疫学フロンティア研究センター
Creator Name
Tamashima, Hiroto
玉島, 博人
タマシマ, ヒロト
Affiliation
Affiliation Name
Graduate School of Pharmaceutical Science, Kyushu University
九州大学大学院薬学府創薬科学専攻
Author PID
80623462
Creator Name
Akiyama, Hisako
秋山, 央子
アキヤマ, ヒサコ
Affiliation
Affiliation Name
Juntendo Advanced Research Institute for Health Science, Juntendo University
順天堂大学
Affiliation
Affiliation Name
RIKEN Center for Brain Science
理化学研究所脳神経科学研究センター
Creator Name
Kimuro, Yusuke
木室, 佑亮
キムロ, ユウスケ
Affiliation
Affiliation Name
Graduate School of Pharmaceutical Science, Kyushu University
九州大学大学院薬学府創薬科学専攻
Author PID
K007240
0000-0003-2182-3914
Creator Name
Yoritate, Makoto
寄立, 麻琴
ヨリタテ, マコト
Affiliation
Affiliation Name
Graduate School of Pharmaceutical Science, Kyushu University
九州大学大学院薬学研究院創薬科学部門
Author PID
K008016
Creator Name
Matoba, Hiroaki
的場, 博亮
マトバ, ヒロアキ
Affiliation
Affiliation Name
Graduate School of Pharmaceutical Science, Kyushu University
九州大学大学院薬学研究院創薬科学部門
Author PID
30610951
Creator Name
Imamura, Akihiro
今村, 彰宏
イマムラ, アキヒロ
Affiliation
Affiliation Name
Department of Applied Bioorganic Chemistry and Institute for Glyco-core Research (iGCORE), Gifu University
岐阜大学
Author PID
20203002
Creator Name
Ishida, Hideharu
石田, 秀治
イシダ, ヒデハル
Affiliation
Affiliation Name
Department of Applied Bioorganic Chemistry and Institute for Glyco-core Research (iGCORE), Gifu University
岐阜大学
Author PID
40312946
Creator Name
Yamasaki, Sho
山崎, 晶
ヤマサキ, ショウ
Affiliation
Affiliation Name
Department of Molecular Immunology Research Institute for Microbial Diseases, Osaka University
大阪大学微生物病研究所
Affiliation
Affiliation Name
Laboratory of Molecular Immunology Immunology Frontier Research Center, Osaka University
大阪大学免疫学フロンティア研究センター
Author PID
K006452
0000-0003-3420-555X
Creator Name
Hirai, Go
平井, 剛
ヒライ, ゴウ
Affiliation
Affiliation Name
Graduate School of Pharmaceutical Science, Kyushu University
九州大学大学院薬学研究院創薬科学部門
Language
English
Publisher
Wiley
Date
2023-04-25
Source Title
Angewandte Chemie International Edition
Vol
62
Issue
22
First Page
e202302569
Publication Type
Accepted Manuscript
Access Rights
open access
Rights
This is the peer reviewed version of the following article: T. Ikazaki, E. Ishikawa, H. Tamashima, H. Akiyama, Y. Kimuro, M. Yoritate, H. Matoba, A. Imamura, H. Ishida, S. Yamasaki, G. Hirai, Angew. Chem. Int. Ed. 2023, 62, e202302569. , which has been published in final form at https://doi.org/10.1002/anie.202302569. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
Related DOI
isVersionOf
https://doi.org/10.1002/anie.202302569
Abstract Glycoconjugate analogues in which the sp^3-hybridized C2 position of the carbohydrate structure (normally bearing a hydroxy group) is converted into a compact sp2-hybridized exomethylene group are exp...ected to have unique biological activities. We established ligand-controlled Tsuji–Trost-type glycosylation methodology to directly prepare a variety of these 2-exomethylene 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.show more

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Details

PISSN
1433-7851
EISSN
1521-3773
NCID
AA0052535X
Record ID
7173600
Subject Terms
Glucosylceramides
Glycan Analogues
Immune Receptors
Reagent-Controlled Glycosylation
Tsuji–Trost Allylation
Notes
The title differs from the publisher's edition. For the title of the author's edition, see Other Titles.
出版社版とはタイトルが異なる。著者版のタイトルについては、その他のタイトルを見よ。
Type
Research Article
Funding Information
Funder Name
Japan Society for the Promotion of Science (JSPS)
日本学術振興会
Award Number
21K19053
Award Title
中分子グライコミメティクスの開拓
Funder Name
Japan Society for the Promotion of Science (JSPS)
日本学術振興会
Award Number
21H02070
Award Title
Synthetic chemistry for the development of oligosaccharide-type sialidase inhibitors
遷移状態ー基質ハイブリッドアナログ型酵素阻害剤の創製
Funder Name
Japan Society for the Promotion of Science (JSPS)
日本学術振興会 J
Award Number
22K14683
Award Title
Development of a new method for generating glycosyl radical and application to C-glycosylation
新規グリコシルラジカル発生法の開発と無保護C-グリコシル化反応への応用
Funder Name
Japan Agency for Medical Research and Development
日本医療研究開発機構
Funder Name
Mizutani Foundation for Glycoscience
水谷糖質科学振興財団
Funder Name
Takeda Science Foundation
武田科学振興財団
Created Date 2024.04.22
Modified Date 2024.04.25

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