Niggemeyer Georg B, Danglad-Flores José A, Seeberger Peter H
Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Potsdam 14476, Germany.
Freie Universität Berlin, Institute of Chemistry and Biochemistry, Berlin 14195, Germany.
J Am Chem Soc. 2025 Jan 15;147(2):1649-1655. doi: 10.1021/jacs.4c11798. Epub 2024 Dec 31.
Automated glycan assembly (AGA) streamlines the synthesis of complex oligosaccharides. The reducing end of the oligosaccharide serves as an attachment site to the polymer support to liberate a free reducing end or an aminopentanol for ready conjugation to carrier proteins or surfaces. The facile installation of different aglycons on oligosaccharides has not been possible via AGA until now. Here, we describe a latent-active approach enabled by a traceless photolabile linker that allows for bidirectional AGA and ready introduction of various aglycons. Oligosaccharide thioglycosides, peptidoglycans, prototypical saponins, and click-chemistry-based conjugates are synthesized to illustrate the versatility of the method.
自动化聚糖组装（AGA）简化了复杂寡糖的合成。寡糖的还原端作为与聚合物载体的连接位点，以释放出游离的还原端或氨基戊醇，以便于与载体蛋白或表面进行偶联。到目前为止，通过AGA还无法在寡糖上轻松安装不同的苷元。在此，我们描述了一种由无痕光不稳定连接子实现的潜在活性方法，该方法允许双向AGA并能方便地引入各种苷元。合成了寡糖硫代糖苷、肽聚糖、典型皂苷和基于点击化学的缀合物，以说明该方法的通用性。
