Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides by a Covalent Catch-and-Release Approach.

Francesco Palmieri, Chin Huang, Digantkumar Chapla, Kelley W Moremen, Geert-Jan Boons

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Article in Angewandte Chemie (International ed. in English), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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Authors and funding

5 authors.

Francesco PalmieriDivision of Chemical Biology and Drug Discovery, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, Utrecht, the Netherlands.

Chin HuangComplex Carbohydrate Research Center, University of Georgia, Athens, Georgia, USA.

Digantkumar ChaplaComplex Carbohydrate Research Center, University of Georgia, Athens, Georgia, USA.

Kelley W MoremenComplex Carbohydrate Research Center, University of Georgia, Athens, Georgia, USA.

Geert-Jan BoonsDivision of Chemical Biology and Drug Discovery, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, Utrecht, the Netherlands.

Funding

3-O-sulfation of heparan sulfate as a regular of protein functionR01HL151617 · NHLBI · UNIVERSITY OF GEORGIA · PI BOONS, GEERT-JAN, MOREMEN, KELLEY W. · 2020 to 2023

$1.8M

EC H2020 Marie Curie doctorate COFUND RESCUENHLBI NIH HHS R01 HL151617

6 · The paper itself

Abstract

A covalent catch-and-release approach is described for the chemoenzymatic synthesis of HS oligosaccharides. It exploits that a glycan modified by a hydrazide tag can under mild acidic conditions efficiently be reacted with an aldehyde-containing resin to give an immobilized hydrazone product. The hydrazone is stable under neutral conditions, allowing stringent washing conditions to remove all other components. The product can be released by transiminolysis using aqueous hydroxylamine, which, after evaporation, yields a compound that can be immediately employed in the next cycle of modification. As many as 11 consecutive transformations could be performed to give a homogenous octasaccharide having a complex pattern of sulfation and epimerization. The methodology provides opportunities to prepare convenient collections of biologically important HS oligosaccharides for structure-function studies.

Indexed as

Heparan SulfateOligosaccharidesHydrazonesHeparan SulfateHydrazonesOligosaccharidescarbohydrateschemoenzymaticenzymesheparan sulfatehydrazonessolid‐phase extraction

Identifiers

PMID42438938

DOI10.1002/anie.2903805

PMCPMC13528540

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