dc.contributor.author | Zhang, Xing | |
dc.contributor.author | Xu, Yongmei | |
dc.contributor.author | Hsieh, Po Hung | |
dc.contributor.author | Liu, Jian | |
dc.contributor.author | Lin, Lei | |
dc.contributor.author | Schmidt, Eric P. | |
dc.contributor.author | Linhardt, Robert J. | |
dc.date | 2017 | |
dc.date.accessioned | 2022-06-23T04:20:06Z | |
dc.date.available | 2022-06-23T04:20:06Z | |
dc.date.issued | 2017-01-01 | |
dc.identifier.citation | 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. | |
dc.identifier.issn | 14770520 | |
dc.identifier.uri | https://hdl.handle.net/20.500.13015/5342 | |
dc.identifier.uri | https://doi.org/10.1039/C6OB02603F | |
dc.description | Organic and Biomolecular Chemistry, 15, 1222–1227 | |
dc.description | 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. | |
dc.description.abstract | 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. | |
dc.description.sponsorship | National Institutes of Health | |
dc.language | en_US | |
dc.language.iso | ENG | |
dc.publisher | Royal Society of Chemistry | |
dc.relation.ispartof | The Linhardt Research Labs Online Collection | |
dc.relation.ispartof | Rensselaer Polytechnic Institute, Troy, NY | |
dc.relation.ispartof | Organic and Biomolecular Chemistry | |
dc.relation.uri | https://harc.rpi.edu/ | |
dc.subject | Biology | |
dc.subject | Chemistry and chemical biology | |
dc.subject | Chemical and biological engineering | |
dc.subject | Biomedical engineering | |
dc.title | Chemoenzymatic synthesis of unmodified heparin oligosaccharides: Cleavage of p-nitrophenyl glucuronide by alkaline and Smith degradation | |
dc.type | Article | |
dcterms.accessRights | A full text version is available in DSpace@RPI | |
dcterms.isPartOf | Journal | |
dcterms.isVersionOf | https://doi.org/10.1039/C6OB02603F | |
dc.rights.holder | In Copyright : this Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). https://rightsstatements.org/page/InC/1.0/ | |
dc.creator.identifier | https://orcid.org/0000-0003-2219-5833 | |
dc.relation.department | The Linhardt Research Labs. | |
dc.relation.department | The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS) | |
rpi.description.pages | 1222-1227 | |
rpi.description.volume | 15 | |