Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China; Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Potsdam 14476, Germany.
Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China.
Chin J Nat Med. 2020 Aug;18(8):628-632. doi: 10.1016/S1875-5364(20)30075-3.
D-Glycero-D-mannno-heptose 1β, 7-bisphosphate (HBPβ) is an important intermediate for constructing the core structure of Gram-negative bacterial lipopolysaccharides and was reported as a pathogen-associated molecular pattern (PAMP) that regulates immune responses. HBPβ with 3-O-amyl amine linker and its monophosphate derivative D-glycero-D-mannno-heptose 7-phosphate (HP) with 1α-amyl amine linker have been synthesized as candidates for immunity study of HBPβ. The O3-amyl amine linker of heptose was installed by dibutyltin oxide-mediated regioselective alkylation under fine-tuned protecting condition. The stereoselective installation of 1β-phosphate ester was achieved by NIS-mediated phosphorylation at low temperature. The strategy for installation of 3-O-amyl amine linker onto HBP derivative can be expanded to the syntheses of other conjugation-ready carbohydrates bearing anomeric phosphoester.
D-甘油-D-甘露庚糖 1β,7-双磷酸（HBPβ）是构建革兰氏阴性细菌脂多糖核心结构的重要中间体，被报道为一种调节免疫反应的病原体相关分子模式（PAMP）。具有 3-O- 戊基胺连接子的 HBPβ及其单磷酸衍生物 D-甘油-D-甘露庚糖 7-磷酸（HP）具有 1α-戊基胺连接子，已被合成作为 HBPβ免疫研究的候选物。庚糖的 O3- 戊基胺连接子通过在精细调节的保护条件下，使用二丁基氧化锡介导的区域选择性烷基化进行安装。通过在低温下通过 NIS 介导的磷酸化实现 1β-磷酸酯的立体选择性安装。将 3-O-戊基胺连接子安装到 HBP 衍生物上的策略可以扩展到其他具有糖端磷酸酯的可缀合碳水化合物的合成中。
