Synthesis and biological activity of ganglioside GM3 analogues with a (S)-CHF-Sialoside linkage and an alkyne tag
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...
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| Veröffentlicht in: | Glycoconjugate journal 2023-06, Vol.40 (3), p.333-341 |
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| container_title | Glycoconjugate journal |
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| creator | Ota, Eisuke Takeda, Daiki Oonuma, Kana Kato, Marie Matoba, Hiroaki Yoritate, Makoto Sodeoka, Mikiko Hirai, Go |
| description | 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. |
| doi_str_mv | 10.1007/s10719-023-10111-0 |
| format | Article |
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S
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| subjects | Biochemistry Biological activity Biology Biomedical and Life Sciences Enzymes Fatty acids G(M3) Ganglioside - analogs & derivatives Ganglioside GM3 Life Sciences Lipids Localization Pathology Proteins Research Article |
| title | Synthesis and biological activity of ganglioside GM3 analogues with a (S)-CHF-Sialoside linkage and an alkyne tag |
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