Synthetic Zwitterionic <i>Streptococcus pneumoniae</i> Type 1 Oligosaccharides Carrying Labile <i>O</i> ‐Acetyl Esters

نویسندگان

چکیده

We here report the first total synthesis of Streptococcus pneumoniae serotype 1 (Sp1) oligosaccharide, a unique zwitterionic capsular polysaccharide carrying labile O-acetyl esters. The target oligosaccharides, featuring rare a-2,4-diamino-2,4,6-trideoxy galactose (AAT) and a-galacturonic acids, were assembled up to 9-mer level, in highly stereoselective manner using trisaccharide building blocks. lability esters imposed careful deprotection scheme prevent migration hydrolysis. was investigated detail at various pD values NMR spectroscopy, show that hydrolysis C-3-O-acetyl readily takes place under neutral conditions. Structural investigation showed oligomers adopt right-handed helical structure with acetyl exposed on periphery helix close proximity neighboring AAT residues, thereby imposing conformational restrictions AATα1−4GalA(3OAc) glycosidic linkages, supporting shape polysaccharide, has been proposed be critical for its biological activity.

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ژورنال

عنوان ژورنال: Angewandte Chemie

سال: 2022

ISSN: ['1521-3773', '1433-7851', '0570-0833']

DOI: https://doi.org/10.1002/ange.202211940