Synthesis and biological activity of ganglioside GM3 analogues with a (S)-CHF-Sialoside linkage and an alkyne tag.

Autor: Ota E; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan., Takeda D; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-Ku, Fukuoka, 812-8582, Japan., Oonuma K; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan.; RIKEN Center for Sustainable Resource Science, 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan., Kato M; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan., Matoba H; 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., Sodeoka M; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan. sodeoka@riken.jp.; RIKEN Center for Sustainable Resource Science, 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan. sodeoka@riken.jp., Hirai G; Synthetic Organic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan. gohirai@phar.kyushu-u.ac.jp.; RIKEN Center for Sustainable Resource Science, 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan. gohirai@phar.kyushu-u.ac.jp.; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1, Maidashi, Higashi-Ku, Fukuoka, 812-8582, Japan. gohirai@phar.kyushu-u.ac.jp.
Jazyk: angličtina
Zdroj: Glycoconjugate journal [Glycoconj J] 2023 Jun; Vol. 40 (3), pp. 333-341. Date of Electronic Publication: 2023 Mar 20.
DOI: 10.1007/s10719-023-10111-0
Abstrakt: The alkyne tag, consisting of only two carbons, is widely used as a bioorthogonal functional group due to its compactness and nonpolar structure, and various probes consisting of lipids bearing an alkyne tag have been developed. Here, we designed and synthesized analogues of ganglioside GM3 bearing an alkyne tag in the fatty acid moiety and evaluated the effect of the alkyne tag on the biological activity. To eliminate the influence of other factors such as degradation of the glycan chain when evaluating biological activity in a cellular environment, we introduced the tag into sialidase-resistant (S)-CHF-linked GM3 analogues developed by our group. The designed analogues were efficiently synthesized by tuning the protecting group of the glucosylsphingosine acceptor. The growth-promoting effect of these analogues on Had-1 cells was dramatically altered depending upon the position of the alkyne tag.
(© 2023. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)
Databáze: MEDLINE
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