Synthesis of Glucuronic Acid-Containing Fragments of a Heparin Sulfate Mimetic

Synthesis of the Key Saccharide Fragments of the Glucuronic Acid-Containing Repeat Unit of Pentosan Polysulfate, a Heparin Sulfate Mimetic: M. G. Banwell, S. Marshall (née Campbell), J. S. Ward, B. D. Schwartz
SynOpen 2023, 7, 381–393

The glycosaminoglycan polysaccharide pentosan polysulfate (PPS) – marketed under the brand name ELMIRON® – is a synthetically derived, heparin-like mimetic that is used clinically for alleviating bladder pain, as well as being used to treat osteoarthritis in dogs and horses. The preparation of PPS is complex and starts with the isolation from beech tree bark of the hemi-cellulose-type polysaccharide xylan, followed by sulfation, oxidative depolymerization, salt-forming and membrane-based nano-filtration steps which lead to a heterogeneous product within the 3,000 to 10,000 amu range. Recently, a collaboration between the group of Professors Martin G. Banwell from Jinan University, Guangzhou (P. R. of China) and Brett D. Schwartz from The Australian National University (Canberra, Australia) resulted in a novel approach to key saccharide fragments of PPS.

Professor Banwell said: “This work defines a pathway by which the key parts of a clinically deployed oligosaccharide can be prepared and should allow for the development of improved variants.”

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