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

文献类型：期刊论文

作者Peng, Jiarong2,3; Hao, Tianhui1,2; Ma, Wenjing1,2; Xu, Zhuojia2; Li, Tiehai1,2,3
刊名CHINESE JOURNAL OF CHEMISTRY
出版日期2024-09-16
页码6
关键词Acinetobacter baumannii Capsular polysaccharide Legionaminic acid Bacterial oligosaccharide Chemoenzymatic synthesis Stereoselective glycosylation Enzyme-catalyzed synthesis Synthesis design
ISSN号1001-604X
DOI10.1002/cjoc.202400794
通讯作者Xu, Zhuojia(xuzhuojia@simm.ac.cn) ; Li, Tiehai(tiehaili@simm.ac.cn)
英文摘要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-construct alpha-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 subsequent alpha 2,6-sialyltransferase-catalyzed glycosylation, was achieved to synthesize the pentasaccharide.
WOS关键词5,7-DIAMINO-3,5,7,9-TETRADEOXYNON-2-ULOSONIC ACIDS ; CARBOHYDRATE VACCINES ; HOSPITALS ; CHEMISTRY ; UNIT
资助项目National Natural Science Foundation of China[22077130] ; National Natural Science Foundation of China[22377134] ; Shanghai Municipal Science and Technology Major Project
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001313711900001
出版者WILEY-V C H VERLAG GMBH
源URL[http://119.78.100.183/handle/2S10ELR8/313347]  
专题中国科学院上海药物研究所
通讯作者Xu, Zhuojia; Li, Tiehai
作者单位1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Chem Biol, Shanghai 201203, Peoples R China
3.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Jiangsu, Peoples R China
推荐引用方式
GB/T 7714		 Peng, Jiarong,Hao, Tianhui,Ma, Wenjing,et al. Chemoenzymatic Synthesis of Common Legionaminic Acid-Containing Pentasaccharide of Capsular Polysaccharides from Acinetobacter baumannii K27 and K44[J]. CHINESE JOURNAL OF CHEMISTRY,2024:6.
APA Peng, Jiarong,Hao, Tianhui,Ma, Wenjing,Xu, Zhuojia,&Li, Tiehai.(2024).Chemoenzymatic Synthesis of Common Legionaminic Acid-Containing Pentasaccharide of Capsular Polysaccharides from Acinetobacter baumannii K27 and K44.CHINESE JOURNAL OF CHEMISTRY,6.
MLA Peng, Jiarong,et al."Chemoenzymatic Synthesis of Common Legionaminic Acid-Containing Pentasaccharide of Capsular Polysaccharides from Acinetobacter baumannii K27 and K44".CHINESE JOURNAL OF CHEMISTRY (2024):6.

入库方式： OAI收割

来源：上海药物研究所

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