Chemoenzymatic Synthesis of Common Legionaminic Acid−Containing Pentasaccharide of Capsular Polysaccharides from Acinetobacter baumannii K27 and K44
Jiarong Peng , Tianhui Hao , Wenjing Ma , Zhuojia Xu , Tiehai Li
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (1) : 33 -38.
Chemoenzymatic Synthesis of Common Legionaminic Acid−Containing Pentasaccharide of Capsular Polysaccharides from Acinetobacter baumannii K27 and K44
Comprehensive Summary: 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 α-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 α2, 6-sialyltransferase-catalyzed glycosylation, was achieved to synthesize the pentasaccharide.
Acinetobacter baumannii / Capsular polysaccharide / Legionaminic acid / Bacterial oligosaccharide / Chemoenzymatic synthesis / Stereoselective glycosylation / Enzyme-catalyzed synthesis / Synthesis design
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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