Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

• Anne-Katrin Späte,
• Verena F. Schart,
• Julia Häfner,
• Andrea Niederwieser,
• Thomas U. Mayer and
• Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

• Biology and Konstanz Research School Chemical Biology (KoRS-CB), Universitätsstraße 10, 78457 Konstanz, Germany 10.3762/bjoc.10.232 Abstract Monitoring glycoconjugates has been tremendously facilitated by the development of metabolic oligosaccharide engineering. Recently, the inverse-electron-demand

• ; metabolic oligosaccharide engineering; Introduction The glycan chains of glycoproteins and lipids have been shown to be involved in numerous biological recognition and regulation events [1]. Glycan research, especially the visualization of glycoconjugates in vitro and in vivo, has significantly profited

• from the recent developments in the area of metabolic oligosaccharide engineering (MOE) and the chemical reporter strategy [2][3][4]. In this approach, functional groups with a unique reactivity are incorporated into glycoconjugates via the cell’s biosynthetic machinery and are subsequently reacted in