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

作者机构：Key Laboratory of Carbohydrate Chemistry and BiotechnologyMinistry of EducationSchool of BiotechnologyJiangnan UniversityWuxi 214122China Department of Biomolecular SystemsMax Planck Institute of Colloids and InterfacesPotsdam 14476Germany Wuxi School of MedicineJiangnan UniversityWuxi 214122China 

出 版 物：《Chinese Journal of Natural Medicines》 (中国天然药物（英文版）)

年 卷 期：2020年第18卷第8期

页      面：628-632页

核心收录：

学科分类：1007[医学-药学(可授医学、理学学位)] 100701[医学-药物化学] 10[医学] 

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 

主　　题：HBPβ-3-O-amyl amine HP-1α-O-amyl amine 3-O-Alkylation NIS-mediated phosphorylation 

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 ***βwith 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 *** stereoselective installation of 1β-phosphate ester was achieved by NIS-mediated phosphorylation at low *** 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.