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CC BY 4.0 · SynOpen 2023; 07(03): 381-393
DOI: 10.1055/a-2126-0346
paper

Synthesis of the Key Saccharide Fragments of the Glucuronic Acid-Containing Repeat Unit of Pentosan Polysulfate, a Heparin Sulfate Mimetic

Martin G. Banwell  ∗
a   Institute for Advanced and Applied Chemical Synthesis, College of Pharmacy, Jinan University, Guangzhou, Guangdong, 510632, P. R. of China
,
Sarah Marshall
b   Research School of Chemistry, The Australian National University, Canberra, ACT 2601, Australia
,
Jas S. Ward
b   Research School of Chemistry, The Australian National University, Canberra, ACT 2601, Australia
,
Brett D. Schwartz∗
b   Research School of Chemistry, The Australian National University, Canberra, ACT 2601, Australia
› Author AffiliationsWe thank Jinan University, the Australian National University and Beta Therapeutics Pty Ltd for financial support.
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Abstract

Suitably protected mono- and di-saccharide residues associated with the glucuronic acid-containing repeat unit related to pentosan polysulfate have been prepared. The stereo-controlled coupling, using trichloroacetimidate chemistry, of certain of these is also described and the structure of a disaccharide so-formed has been confirmed by single-crystal X-ray analysis.

Key Words

heparanase - mimetic - pentosan polysulfate (PPS) - trichloroacetimidate - xylose

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2126-0346. Included are an outline of the general synthetic protocols employed in this study, plots derived from the single-crystal X-ray analyses of compounds 17, 18 and 40 together with summaries of key NMR spectral data used to establish the structures of compounds 3, 12 and 13, 31 and 32 and 34. Copies of the 1H and 13C NMR spectra of compounds 2, 3, 4 (R =Me), 5, 7, 9, 11–17, 19, 21–34 and 36–40 are also provided.
  • Supporting Information


Publication History

Received: 08 May 2023

Accepted after revision: 07 July 2023

Accepted Manuscript online:
10 July 2023

Article published online:
21 August 2023

© 2023. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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