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

Natsuho Moritsuka,

Noriaki Kiya,

Takahiro Moriyama

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 11909 - 11920

Опубликована: Авг. 9, 2024

Melibiosamine (Gal-α(1,6)-GlcNH2), consisting of galactose and glucosamine linked by an α(1,6)-glycosidic bond, is artificial disaccharide derivative that selectively inhibits the proliferation K562 tumor cells relative to HUC-F2 normal cells. In this study, we employed a linkage-editing strategy synthesize CH2- CHF-linked melibiosamine analogs through chemo- stereoselective hydrogenation fluorovinyl-C-glycoside. (R)-CHF-Melibiosamine exhibited more potent antiproliferative activity than O-linked melibiosamine, while (S)-CHF-melibiosamine was less potent.

Язык: Английский

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

Natsuho Moritsuka,

Noriaki Kiya,

Takahiro Moriyama

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 11909 - 11920

Опубликована: Авг. 9, 2024

Melibiosamine (Gal-α(1,6)-GlcNH2), consisting of galactose and glucosamine linked by an α(1,6)-glycosidic bond, is artificial disaccharide derivative that selectively inhibits the proliferation K562 tumor cells relative to HUC-F2 normal cells. In this study, we employed a linkage-editing strategy synthesize CH2- CHF-linked melibiosamine analogs through chemo- stereoselective hydrogenation fluorovinyl-C-glycoside. (R)-CHF-Melibiosamine exhibited more potent antiproliferative activity than O-linked melibiosamine, while (S)-CHF-melibiosamine was less potent.

Язык: Английский

Процитировано

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