TY - JOUR
T1 - Linkage-Editing of Melibiosamine
T2 - Synthesis and Biological Evaluation of CH2- and CHF-Linked Analogs
AU - Moritsuka, Natsuho
AU - Kiya, Noriaki
AU - Moriyama, Takahiro
AU - Koshino, Hiroyuki
AU - Yoritate, Makoto
AU - Matoba, Hiroaki
AU - Hirai, Go
N1 - Publisher Copyright:
© 2024 American Chemical Society.
PY - 2024
Y1 - 2024
N2 - Melibiosamine (Gal-α(1,6)-GlcNH2), 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 CH2- 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.
AB - Melibiosamine (Gal-α(1,6)-GlcNH2), 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 CH2- 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.
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U2 - 10.1021/acs.joc.4c01143
DO - 10.1021/acs.joc.4c01143
M3 - Article
AN - SCOPUS:85201052490
SN - 0022-3263
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
ER -