Biology; Chemistry and chemical biology; Chemical and biological engineering; Biomedical engineering
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Chemoenzymatic synthesis of unmodified heparin oligosaccharides: Cleavage of p-nitrophenyl glucuronide by alkaline and Smith degradation, X. Zhang, Y. Xu, J. Liu, L. Lin, E. Schmidt, R.J. Linhardt, Organic and Biomolecular Chemistry, 15, 1222–1227, 2017.
A heparin oligosaccharide having a completely natural structure was successfully synthesized through a chemoenzymatic approach using an unnatural glycosyl acceptor, p-nitrophenyl glucuronide (GlcA-pNP). The use of an inexpensive and commercially available GlcA-pNP acceptor facilitates oligosaccharide recovery and purification on C-18 resin during chemoenzymatic synthesis. Oligosaccharide chain extension and modification afforded a heptasaccharide with gluconic acid residues at its reducing and non-reducing ends. Treatment with periodate oxidation followed by Smith degradation or alkaline elimination resulted in the selective cleavage of vicinal diol-containing glucronic acid residues affording highly sulfated heparin pentasaccharide having a completely natural structure. This methodology should facilitate the chemoenzymatic synthesis of a family of highly sulfated heparin oligosaccharides with unmodified structures for biological evaluation.;
Organic and Biomolecular Chemistry, 15, 1222–1227; Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
The Linhardt Research Labs.; The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS);
Royal Society of Chemistry
The Linhardt Research Labs Online Collection; Rensselaer Polytechnic Institute, Troy, NY; Organic and Biomolecular Chemistry; https://harc.rpi.edu/;