Total Synthesis of an Aeromonas hydrophila Pt679 O-Antigen Pentasaccharide Repeat Unit Containing β- l -Rha, β- d -QuiNAc, and α- d -Fuc3NAc
Abstract
The total synthesis of the complex pentasaccharide repeating unit related to the O-polysaccharide from Aeromonas hydrophila Pt679 is reported. Suitably protected derivatives of the rare β- d -QuiNAc and α- d -Fuc3NAc units are synthesized from d -glucosamine hydrochloride and 1,2;5,6-di- O -isopropylidene-α- l -allofuranose, respectively, and used for stereoselective glycosylation. The 1,2- cis rhamnosidic linkage is successfully accomplished using picoloyl-mediated hydrogen bond-assisted aglycon delivery (HAD method). The target pentasaccharide in the form of its 2-aminoethyl glycoside is ready for further conjugation through the terminal amine functionality without hampering the reducing end stereochemistry.
Fields of Study & Subjects
Carbohydrate Chemistry and Synthesis
Glycosylation and Glycoproteins Research
Organic Chemistry Synthesis Methods
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Volume
- 91
- Issue
- 7
- Pages
- 2928–2938
- Publication date
- 9 February 2026
- Language
- EN