Concise Synthesis of Lactococcus garvieae Lipoteichoic Acids Through an Additive-Modulated Preactivation Protocol and the Immunological Studies

作     者：Tianlu Li Tong Li Yue Yang Haoru Zhuang Jianwu Lv Ning Zhou Miaomiao Zhang Fengshan Wang Yiqun Geng Richard R.Schmidt Peng Peng 

作者机构：National Glycoengineering Research CenterShandong Key Laboratory of Carbohydrate Chemistry and GlycobiologyNMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate Based MedicineShandong UniversityQingdao 266237 State Key Laboratory of Bioactive Substance and Function of Natural MedicinesInstitute of Materia MedicaChinese Academy of Medical Sciences and Peking Union Medical CollegeBeijing 100050 Department of ChemistryUniversity of KonstanzD-78457 Konstanz 

出 版 物：《CCS Chemistry》 (中国化学会会刊（英文）)

年 卷 期：2024年第6卷第2期

页      面：403-414页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基　　金：supported by the National Natural Science Foundation of China(grant nos.21977063,92053110,and 22177061) the National Key Research and Development Program of China(grant no.2018YFA0902000) the China Postdoctoral Science Foundation(grant no.2020M680090) the Qilu Youth Scholar Program of Shandong University,the Central Government Guide Local Science and Technology Development Funds(grant no.YDZX20203700002579) the Nonprofit Central Research Institute Fund of Chinese Academy of Medical Sciences(grant no.2021-RC350-002) the CAMS Innovation Fund for Medical Sciences(CIFMS)(grant no.2021-1-I2M-026) 

主　　题：1,2-cis glycosidation stereoselectivity lipoteichoic acid total synthesis additive-modulated trichloroacetimidate glycosidation immune response 

摘      要：Lipoteichoic acids(LTAs)are macroamphiphiles composed of alditol,lipid,phosphate,and carbohydrate *** to their inherent complexity,it is a severe challenge to access LTAs with structural integrity from natural sources for biological or immunological ***,we describe the first total synthesis of Lactococcus garvieae LTA(type II LTA),containing five distinct 1,2-cis gluco/galactopyranosidic linkages,via a novel additive-modulated O-glycosyl trichloroacetimidate preactivation glycosidation *** strategy features(1)high glycosidation yields and excellent 1,2-cis stereoselectivities independent of the donor anomeric configuration,(2)common and inexpensive reagents as promoters and additives,(3)application to standard glycosyl imidate donors without resorting to participating protection,and(4)general application to reactive and less reactive glycosyl ***,via the precise stereocontrolled construction of three galactopyranosidic and two glucopyranosidic bonds on a multigram scale,a series of structurally well-defined LTA molecules were successfully *** evaluation of these type II synthetic LTAs showed a structure–activity relationship in the stimulation of a proinflammatory response.