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Total Synthesis of a Rare-Sugar-Enriched O-Antigenic Tetrasaccharide Repeating Unit of Acinetobacter lwoffii EK30A
Supratim Jana1, Mrinmoy Manash Bharali1,2, Abhishek Santra1,2
1Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500007, India.
Abstract:
Herein, we communicate a concise synthetic strategy for the first total synthesis of the O-antigenic tetrasaccharide repeating unit of Acinetobacter lwoffii EK30A polysaccharide. The structurally unique tetrasaccharide possesses three consecutive 1,2-cis-glycosidic linkages and two rare sugar units, i.e., d-FucpNAc and d-Quip4NAc. All functionalized monosaccharides were efficiently synthesized from naturally abundant and inexpensive d-galactose to make the synthetic route affordable and convenient. The tetrasaccharide was synthesized using highly stereoselective, convergent (1 + 2 + 1) and carefully optimizing a high-yielding glycosylation strategy.
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