Toward the chemoenzymatic synthesis of heparan sulfate oligosaccharides: Oxidative cleavage of p-nitrophenyl group with ceric ammonium salts

Chao Cai, Lingyun Li, Cate Harvey, Jian Liu, Robert J. Linhardt

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12 Scopus citations

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.

Original languageEnglish
Pages (from-to)4471-4474
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number33
DOIs
StatePublished - 14 Aug 2013
Externally publishedYes

Keywords

  • Ceric ammonium salt
  • Chemoenzymatic synthesis para-Nitrophenyl glucuronic acid
  • Deprotection
  • Heparan sulfate oligosaccharides

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