Linkage-Editing of Melibiosamine: Synthesis and Biological Evaluation of CH 2 - and CHF-Linked Analogs.

Autor: Moritsuka N; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Kiya N; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Moriyama T; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Koshino H; RIKEN Center for Sustainable Resource Science, Wako, Saitama 351-0198, Japan., Yoritate M; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Matoba H; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan., Hirai G; Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Sep 06; Vol. 89 (17), pp. 11909-11920. Date of Electronic Publication: 2024 Aug 09.
DOI: 10.1021/acs.joc.4c01143
Abstrakt: Melibiosamine (Gal-α(1,6)-GlcNH 2 ), consisting of galactose and glucosamine linked by an α(1,6)-glycosidic bond, is an artificial disaccharide derivative that selectively inhibits the proliferation of K562 tumor cells relative to HUC-F2 normal cells. In this study, we employed a linkage-editing strategy to synthesize CH 2 - and CHF-linked melibiosamine analogs through chemo- and stereoselective hydrogenation of fluorovinyl- C -glycoside. ( R )-CHF-Melibiosamine exhibited more potent antiproliferative activity than O -linked melibiosamine, while ( S )-CHF-melibiosamine was less potent.
Databáze: MEDLINE