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

被引：11

作者：

Farabi, Kindi ^{[1
]}

Manabe, Yoshiyuki ^{[1
,2
]}

Ichikawa, Hiroaki ^{[1
]}

Miyake, Shuto ^{[1
]}

Tsutsui, Masato ^{[1
]}

Kabayama, Kazuya ^{[1
,2
]}

Yamaji, Toshiyuki ^{[3
]}

Tanaka, Katsunori ^{[4
,5
]}

Hung, Shang-Cheng ^{[6
]}

Fukase, Koichi ^{[1
,2
]}

机构：

[1] Osaka Univ, Grad Sch Sci, Dept Chem, Osaka 5600043, Japan

[2] Osaka Univ, Project Res Ctr Fundamental Sci, Core Med & Sci Collaborat Res & Educ, Osaka 5600043, Japan

[3] Natl Inst Infect Dis, Dept Biochem & Cell Biol, Tokyo 1628640, Japan

[4] RIKEN, Biofunct Synthet Chem Lab, Wako, Saitama 3510198, Japan

[5] Tokyo Inst Technol, Sch Mat & Chem Technol, Dept Chem Sci & Engn, Tokyo 1528552, Japan

[6] Acad Sinica, Genom Res Ctr, Taipei 115, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 24期

关键词：

SHIGA-LIKE TOXIN; SOLID-PHASE SYNTHESIS; INFLUENZA-A VIRUS; SIALIC-ACID; CARBOSILANE DENDRIMERS; CARBOHYDRATE-PROTEIN; SIALOSIDE INHIBITORS; GOLD NANOPARTICLES; BACTERIAL LECTIN; RECEPTOR-BINDING;

D O I：

10.1021/acs.joc.0c01547

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：16014 / 16023

页数：10