College of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, Fujian, P. R. China.
College of Chemistry, Fuzhou University, Fuzhou 350108, P. R. China.
J Org Chem. 2024 May 3;89(9):6364-6370. doi: 10.1021/acs.joc.4c00356. Epub 2024 Apr 22.
Introducing glycans represents an efficient chemical approach to improve the pharmacological properties of therapeutic biomolecules. Herein, we report an efficient synthesis of glycoconjugates through chlorooxime-thiol conjugation. The reactive glycosyl chlorooximes, derived from pyranoses or furanoses, readily couple to a wide range of thiol-containing substrates, including peptides, sugars, and thiophenols. This method features mild reaction conditions and fast kinetics. Capability for aqueous media and gram-scale synthesis demonstrates the potential of this method in the bioconjugation of saccharides with biologically active molecules.
糖基化是一种有效的化学方法，可以改善治疗性生物分子的药理学性质。在此，我们通过氯肟-巯基偶联反应报告了糖缀合物的高效合成方法。反应性糖基氯肟可从吡喃糖或呋喃糖衍生而来，可轻易与多种含巯基的底物（包括肽、糖和硫酚）偶联。该方法具有温和的反应条件和快速的反应动力学。在水相介质和克级规模合成方面的能力，展示了该方法在具有生物活性的分子与糖进行生物偶联方面的潜力。
