Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5271498 | Tetrahedron Letters | 2013 | 4 Pages |
Abstract
We have developed an efficient chemoenzymatic synthesis of heparan sulfate oligosaccharides employing the para-nitrophenyl (p-NP) β-glucuronide as an acceptor compatible with enzymatic elongation and one that significantly simplifies oligosaccharide purification on C-18 resin. Employing ceric ammonium nitrate as oxidative reagent to remove the p-NP group unexpectedly also removed the glucuronic acid residue at the reducing-end, affording a smaller oligosaccharide. The application of ceric ammonium sulfate allowed the removal of the p-NP without concomitant loss of the adjacent glucuronic acid offering a route to longer heparin sulfate oligosaccharide products.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Chao Cai, Lingyun Li, Cate Harvey, Jian Liu, Robert J. Linhardt,