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.
Beilstein J Org Chem. 2013 Nov 7;9:2395-403. doi: 10.3762/bjoc.9.276. eCollection 2013.
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.
我们提出了利用新型的六个不同糖基化砌块的不同功能化模式，固相合成糖基化的寡聚（酰胺胺）。在高效的流动条件下，将硫糖苷键合到具有双键的二亚乙基三胺前体是制备这些砌块的关键步骤，这些砌块适用于全自动化固相合成。通过功能化砌块而不是寡聚骨架的后功能化引入糖配体，可以直接合成具有完全控制单体序列和功能化模式的多价糖缀合物。我们通过合成具有不同数量和间隔的碳水化合物的寡聚物，展示了这种砌块方法的潜力，并且通过组合具有不同单糖和二糖的砌块，也展示了杂多价糖基化模式的可行性。
