Linkage-Editing of Melibiosamine: Synthesis and Biological Evaluation of CH2- and CHF-Linked Analogs

Natsuho Moritsuka, Noriaki Kiya, Takahiro Moriyama, Hiroyuki Koshino, Makoto Yoritate, Hiroaki Matoba, Go Hirai

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
JournalJournal of Organic Chemistry
DOIs
Publication statusAccepted/In press - 2024

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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