Total synthesis of D-glycero-D-mannno-heptose 1β, 7-bisphosphate with 3-O-amyl amine linker and its monophosphate derivative  

作　　者：ZOU Xiao-Peng QIN Chun-Jun HU Jing FU Jun-Jie TIAN Guang-Zong MOSCOVITZ Oren SEEBERGER Peter H. YIN Jian 

机构地区：[1]Key Laboratory of Carbohydrate Chemistry and Biotechnology,Ministry of Education,School of Biotechnology,Jiangnan University,Wuxi 214122,China [2]Department of Biomolecular Systems,Max Planck Institute of Colloids and Interfaces,Potsdam 14476,Germany [3]Wuxi School of Medicine,Jiangnan University,Wuxi 214122,China

出　　处：《Chinese Journal of Natural Medicines》2020年第8期628-632,共5页中国天然药物（英文版）

基　　金：supported by the National Natural Science Foundation of China(Nos.21877052 and 21907039);the Natural Science Foundation of Jiangsu Province(Nos.BK20180030and BK20190575);the High-end Foreign Experts Recruitment Program;National First-class Discipline Program of Light Industry Technology and Engineering(No.LITE2018-14);the 111 Project(No.111-2-06);the Max Planck Society International Partner Group Program;China Scholarship Council(CSC);the Max-Planck Society for generous financial support。

摘　　要：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.HBPβwith 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.

关 键 词：HBPβ-3-O-amyl amine HP-1α-O-amyl amine 3-O-Alkylation NIS-mediated phosphorylation 

分 类 号：R914.5[医药卫生—药物化学]