Lin Mei-Huei, Kuo Yan-Ting, Danglad-Flores José, Sletten Eric T, Seeberger Peter H
Department of Biomolecular Systems, Max-Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14476, Potsdam, Germany.
Department of Chemistry and Biochemistry, Freie Universität Berlin, Arnimallee 22, 14195, Berlin, Germany.
Chemistry. 2024 May 28;30(30):e202400479. doi: 10.1002/chem.202400479. Epub 2024 Apr 17.
The chemical synthesis of complex oligosaccharides relies on efficient and highly reproducible glycosylation reactions. The outcome of a glycosylation is contingent upon several environmental factors, such as temperature, acidity, the presence of residual moisture, as well as the steric, electronic, and conformational aspects of the reactants. Each glycosylation proceeds rapidly and with a high yield within a rather narrow temperature range. For better control over glycosylations and to ensure fast and reliable reactions, a systematic analysis of 18 glycosyl donors revealed the effect of reagent concentration, water content, protecting groups, and structure of the glycosyl donors on the activation temperature. With these insights, we parametrize the first step of the glycosylation reaction to be executed reliably and efficiently.
复杂寡糖的化学合成依赖于高效且高度可重复的糖基化反应。糖基化的结果取决于几个环境因素，如温度、酸度、残留水分的存在，以及反应物的空间、电子和构象方面。每次糖基化在相当窄的温度范围内快速进行且产率很高。为了更好地控制糖基化反应并确保快速可靠的反应，对18种糖基供体进行的系统分析揭示了试剂浓度、含水量、保护基团以及糖基供体结构对活化温度的影响。有了这些认识，我们对糖基化反应的第一步进行参数化，以便可靠而高效地进行。
