Total Synthesis of a Pentasaccharide O‐Glycan from Acinetobacter baumannii
Total Synthesis of a Pentasaccharide O‐Glycan from Acinetobacter baumannii
复制标题
鲍曼不动杆菌五糖 O-聚糖的全合成
DOI：
10.1002/ejoc.202201261
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发表时间：
2022
影响因子：
2.8
通讯作者：
Ragains, Justin R.
中科院分区：
文献类型：
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作者：
Njeri, Dancan K.;Ragains, Justin R.
鲍曼不动杆菌是一种革兰氏阴性菌，与医疗机构中的耐药性和感染相关。了解这种生物体表面分子的生物学作用和抗原性，可能会为通过接种疫苗或开发单克隆抗体预防和治疗感染提供重要的一步。考虑到这一点，我们已经进行了从mA的缀合就绪的五肽O-聚糖的多步合成。鲍曼不动杆菌具有19步的最长线性合成序列。由于其在明显广泛的临床相关菌株中的适应性和毒力中的作用，该靶标特别相关。合成挑战包括制定有效的保护基团策略以及在2，3-二乙酰氨基-2，3-二脱氧-D-葡萄糖醛酸的异头位置和D-半乳糖的4位之间安装特别困难的糖苷键。
Acinetobacter baumanniiis 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 pentasaccharideO‐glycan fromA. baumanniiwith 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 strategy 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.