Towards the chemoenzymatic synthesis of heparan sulfate oligosaccharides: Oxidative cleavage ofp-nitrophenyl group with ceric ammonium salts.
We have developed an efficient chemoenzymatic synthesis of heparan sulfate oligosaccharides employing thepara-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 thep-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 thep-NP without concomitant loss of the adjacent glucuronic acid offering a route to longer heparin sulfate oligosaccharide products.
Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, NY 12180, USA.
Chao
C
Cai
Lingyun
L
Li
Cate
C
Harvey
Jian
J
Liu
Robert J
RJ
Linhardt
Heparan sulfate oligosaccharides; ceric ammonium salt; chemoenzymatic synthesis; deprotection; para-nitrophenyl glucuronic acid