Bakhatan Yasmeen, Sukhran Yonatan, Tsau Lou-Sheng, Lin Sung-Chi, Wang Cheng-Chung, Hurevich Mattan
Institute of Chemistry, The Hebrew University of Jerusalem, Jerusalem, 91904, Israel.
Institute of Chemistry, Academia Sinica, Taipei, 115, Taiwan.
Chemistry. 2025 Aug 7;31(44):e202501249. doi: 10.1002/chem.202501249. Epub 2025 Jul 18.
Optimization of glycosylation temperatures is essential for automated solid-phase glycan assembly. Constructing a reliable optimization system that mimics key reaction components is crucial for increasing the atom economy and the energy efficiency of the process. Although glycosyl acceptors play a pivotal role in glycosylation, evaluating their effect on glycosylation efficiency (GE) is nontrivial. While screening various glycosyl acceptors for optimization is impractical, compromising for simple alkyl acceptors produces results of dubious relevance. We demonstrate that optimization with a modified trans-4-aminocyclohexanol-based acceptor accurately reflects the optimal glycosylation temperature of several glycosyl acceptors, overcoming previous limitations. The contextual use of both n-alkyl and glycan-mimetic acceptors for automated optimization enabled translation of optimized glycosylation temperature to highly efficient solid-phase synthesis (SPS) of disaccharides.
糖基化温度的优化对于自动化固相聚糖组装至关重要。构建一个模拟关键反应组分的可靠优化系统对于提高该过程的原子经济性和能源效率至关重要。尽管糖基受体在糖基化中起关键作用，但评估它们对糖基化效率（GE）的影响并非易事。虽然筛选各种糖基受体进行优化不切实际，但采用简单的烷基受体则会产生相关性存疑的结果。我们证明，使用基于修饰的反式-4-氨基环己醇的受体进行优化能够准确反映几种糖基受体的最佳糖基化温度，克服了先前的局限性。将正烷基和聚糖模拟受体用于自动化优化，能够将优化后的糖基化温度转化为二糖的高效固相合成（SPS）。
