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Total Synthesis of an Aeromonas hydrophila Pt679 O-Antigen Pentasaccharide Repeat Unit Containing β-l-Rha,
Subrata Das1, Sujan De1, Balaram Mukhopadhyay1
1Sweet Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, Nadia 741246, India.
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.
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