Linkage-Editing Pseudo-Glycans: A Reductive α-Fluorovinyl- C -Glycosylation Strategy to Create Glycan Analogs with Altered Biological Activities.

Autor:	Moriyama T; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Yoritate M; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Kato N; Faculty of Agriculture, Setsunan University, 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.; RIKEN Center for Sustainable Resource Science, 2-1, Hirosawa, Wako, Saitama 351-0198, Japan., Saika A; Microbial Research Center for Health and Medicine, National Institutes of Biomedical Innovation, Health and Nutrition, 7-6-8 Asagi-Saito, Ibaraki, Osaka 567-0085, Japan.; Institute of Molecular and Cell Biology, Agency for Science, Technology and Research, 11 Biopolis Way, Helios, Singapore 138667, Singapore., Kusuhara W; Research Institute for Microbial Diseases, Osaka University, Yamadaoka, Suita, Osaka 565-0871, Japan.; Immunology Frontier Research Center, Osaka University, Yamadaoka, Suita, Osaka 565-0871, Japan., Ono S; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Nagatake T; Microbial Research Center for Health and Medicine, National Institutes of Biomedical Innovation, Health and Nutrition, 7-6-8 Asagi-Saito, Ibaraki, Osaka 567-0085, Japan.; Department of Life Sciences, School of Agriculture, Meiji University, 1-1-1 Higashi-Mita, Tama, Kawasaki, Kanagawa 214-8571, Japan., Koshino H; RIKEN Center for Sustainable Resource Science, 2-1, Hirosawa, Wako, Saitama 351-0198, Japan., Kiya N; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Moritsuka N; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Tanabe R; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Hidaka Y; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Usui K; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Chiba S; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Kudo N; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Nakahashi R; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Igawa K; Institute for Materials Chemistry and Engineering, IRCCS, Kyushu University, Kasuga, Fukuoka 816-8580, Japan., Matoba H; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Tomooka K; Institute for Materials Chemistry and Engineering, IRCCS, Kyushu University, Kasuga, Fukuoka 816-8580, Japan., Ishikawa E; Research Institute for Microbial Diseases, Osaka University, Yamadaoka, Suita, Osaka 565-0871, Japan.; Immunology Frontier Research Center, Osaka University, Yamadaoka, Suita, Osaka 565-0871, Japan., Takahashi S; RIKEN Center for Sustainable Resource Science, 2-1, Hirosawa, Wako, Saitama 351-0198, Japan., Kunisawa J; Microbial Research Center for Health and Medicine, National Institutes of Biomedical Innovation, Health and Nutrition, 7-6-8 Asagi-Saito, Ibaraki, Osaka 567-0085, Japan., Yamasaki S; Research Institute for Microbial Diseases, Osaka University, Yamadaoka, Suita, Osaka 565-0871, Japan.; Immunology Frontier Research Center, Osaka University, Yamadaoka, Suita, Osaka 565-0871, Japan., Hirai G; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.; RIKEN Center for Sustainable Resource Science, 2-1, Hirosawa, Wako, Saitama 351-0198, Japan.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2024 Jan 24; Vol. 146 (3), pp. 2237-2247. Date of Electronic Publication: 2024 Jan 09.
DOI:	10.1021/jacs.3c12581
Abstrakt:	The acetal ( O -glycoside) bonds of glycans and glycoconjugates are chemically and biologically vulnerable, and therefore C -glycosides are of interest as more stable analogs. We hypothesized that, if the O -glycoside linkage plays a vital role in glycan function, the biological activities of C -glycoside analogs would vary depending on their substituents. Based on this idea, we adopted a "linkage-editing strategy" for the creation of glycan analogs (pseudo-glycans). We designed three types of pseudo-glycans with CH 2 and CHF linkages, which resemble the O -glycoside linkage in terms of bond lengths, angles, and bulkiness, and synthesized them efficiently by means of fluorovinyl C -glycosylation and selective hydrogenation reactions. Application of this strategy to isomaltose (IM), an inducer of amylase expression, and α-GalCer, which activates iNKT cells, resulted in the discovery of CH 2 -IM, which shows increased amylase production ability, and CHF-α-GalCer, which shows activity opposite that of native α-GalCer, serving as an antagonist of iNKT cells.
Databáze:	MEDLINE
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