Njeri Dancan K, Ragains Justin R
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA 70803.
European J Org Chem. 2022 Dec 19;2022(47). doi: 10.1002/ejoc.202201261. Epub 2022 Dec 16.
is a Gram-negative bacteria associated with drug resistance and infection in healthcare settings. An understanding of both the biological roles and antigenicity of surface molecules of this organism may provide an important step in the prevention and treatment of infection through vaccination or the development of monoclonal antibodies. With this in mind, we have performed the multistep synthesis of a conjugation-ready pentasaccharide -glycan from with a longest linear synthetic sequence of 19 steps. This target is particularly relevant due to its role in both fitness and virulence across an apparently broad range of clinically relevant strains. Synthetic challenges include formulating an effective protecting group scheme as well as the installation of a particularly difficult glycosidic linkage between the anomeric position of a 2,3-diacetamido-2,3-dideoxy-D-glucuronic acid and the 4-position of D-galactose.
是一种与医疗环境中的耐药性和感染相关的革兰氏阴性细菌。了解该生物体表面分子的生物学作用和抗原性，可能是通过疫苗接种或单克隆抗体开发来预防和治疗感染的重要一步。考虑到这一点，我们已经从……进行了一种可用于偶联的五糖聚糖的多步合成，最长线性合成序列为19步。由于该靶点在一系列明显广泛的临床相关菌株的适应性和毒力方面都发挥作用，因此它特别重要。合成挑战包括制定有效的保护基方案，以及在2,3 - 二乙酰氨基 - 2,3 - 二脱氧 - D - 葡萄糖醛酸的异头位置与D - 半乳糖的4 - 位之间安装特别困难的糖苷键。
