Chemoenzymatic Synthesis of Common Legionaminic Acid−Containing Pentasaccharide of Capsular Polysaccharides from Acinetobacter baumannii K27 and K44  

作　　者：Jiarong Peng Tianhui Hao Wenjing Ma Zhuojia Xu Tiehai Li 

机构地区：[1]School of Chinese Materia Medica,Nanjing University of Chinese Medicine,Nanjing,Jiangsu,210023 China [2]State Key Laboratory of Chemical Biology,Shanghai Institute of Materia Medica,Chinese Academy of Sciences,Shanghai,201203 China [3]University of Chinese Academy of Sciences,Beijing,100049 China

出　　处：《Chinese Journal of Chemistry》2025年第1期33-38,共6页中国化学(英文版)

基　　金：financially supported by the National Natural Science Foundation of China(22077130 and 22377134);Shanghai Municipal Science and Technology Major Project.

摘　　要：Acinetobacter baumannii infections pose a great threat to public health owing to upsurging antibiotic resistance.Capsular polysaccharides(CPS)are major virulence determinants of pathogenic bacteria and have attracted much attention as potential targets for vaccine development.However,the obtainability of structurally well-defined CPS-related oligosaccharides remains challenging.Herein,we report an efficient chemoenzymatic strategy for the first total synthesis of common CPS pentasaccharide repeating unit of Acinetobacter baumannii K27 and K44,containing a difficult-to-constructα-linked 5,7-di-N-acetyllegionaminic acid(Leg5,7Ac_(2))residue.The chemical synthesis of a branched tetrasaccharide precursor was accomplished by flexible orthogonal protecting-group manipulations and stereocontrolled glycosylations.Furthermore,the enzyme-catalyzed stereoselective installment of legionaminic acid residue into the tetrasaccharide,using one-pot multienzyme(OPME)synthesis system to produce sugar nucleotide CMP-Leg5,7diN_(3) and subsequentα2,6-sialyltransferase-catalyzed glycosylation,was achieved to synthesize the pentasaccharide.

关 键 词：Acinetobacterbaumanni Capsular polysaccharide Legionaminic acid Bacterial oligosaccharide Chemoenzymatic synthesisl Stereoselectiveglycosylation Enzyme-catalyzed synthesis Synthesis design 

分 类 号：O62[理学—有机化学]