title: Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks.
abstract: We present the solid phase synthesis of carbohydrate-functionalized oligo(amidoamines) with different functionalization patterns utilizing a novel alphabet of six differently glycosylated building blocks. Highly efficient in flow conjugation of thioglycosides to a double-bond presenting diethylentriamine precursor is the key step to prepare these building blocks suitable for fully automated solid-phase synthesis. Introduction of the sugar ligands via functionalized building blocks rather than postfunctionalization of the oligomeric backbone allows for the straightforward synthesis of multivalent glycoligands with full control over monomer sequence and functionalization pattern. We demonstrate the potential of this building-block approach by synthesizing oligomers with different numbers and spacing of carbohydrates and also show the feasibility of heteromultivalent glycosylation patterns by combining building blocks presenting different mono- and disaccharides.
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Research Campus Golm, 14424 Potsdam, Germany, and Institute for Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany.
authors.forename: Felix
authors.initials: F
authors.lastname: Wojcik
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Research Campus Golm, 14424 Potsdam, Germany, and Institute for Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany.
authors.forename: Sinaida
authors.initials: S
authors.lastname: Lel
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Research Campus Golm, 14424 Potsdam, Germany, and Institute for Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany.
authors.forename: Alexander G
authors.initials: AG
authors.lastname: O'Brien
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Research Campus Golm, 14424 Potsdam, Germany, and Institute for Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany.
authors.forename: Peter H
authors.initials: PH
authors.lastname: Seeberger
authors.affiliation: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Research Campus Golm, 14424 Potsdam, Germany, and Institute for Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany.
authors.forename: Laura
authors.initials: L
authors.lastname: Hartmann
keywords: continuous flow; flow chemistry: flow synthesis; glycoligands; multivalency; photochemistry; solid-phase synthesis; thioglycosides; thiol–ene