Gesellschaft Deutscher Chemiker
Keine Benachrichtigungen
Sie haben noch keine Lesezeichen
Abmelden

Artikel

Facile Synthesis of Clickable Unnatural Sugars in the Unprotected and 1,6‐Di‐O‐Acylated Forms for Metabolic Glycan Labeling

Per-O-acetylated unnatural sugars have been widely used in metabolic glycan labeling (MGL), but they can induce non-enzymatic S-glyco-modification. Here we develop facile synthetic routes for unprotected clickable unnatural sugars and their 1,6-di-O-acylated counterparts at the ten-gram scale, the latter enables MGL with high efficiency while avoiding the non-specific S-glyco-modification


Abstract

Clickable unnatural sugars have been widely used in studying glycosylation in living systems via the metabolic glycan labelling (MGL) strategy. Partial protection of unnatural sugars by 1,6-di-O-acylation increases the labelling efficiency while avoiding the non-specific S-glyco-modification. Herein, we report the facile synthesis of a series of clickable unnatural sugars in both the unprotected and 1,6-di-O-acylated forms at the ten-gram scale. By evaluation of the labelling specificity, efficiency, and biocompatibility of various 1,6-di-O-acylated sugars for MGL in cell lines and living mice, we demonstrate that 1,6-di-O-propionylated unnatural sugars are optimal chemical reporters for glycan labelling. The synthetic routes developed in this work should facilitate the widespread use of MGL with no artificial S-glyco-modification for investigating the functional roles of glycans.

Zum Volltext

Überprüfung Ihres Anmeldestatus ...

Wenn Sie ein registrierter Benutzer sind, zeigen wir in Kürze den vollständigen Artikel.