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dc.contributor.authorZhang, Xing
dc.contributor.authorXu, Yongmei
dc.contributor.authorHsieh, Po Hung
dc.contributor.authorLiu, Jian
dc.contributor.authorLin, Lei
dc.contributor.authorSchmidt, Eric P.
dc.contributor.authorLinhardt, Robert J.
dc.date2017
dc.date.accessioned2022-06-23T04:20:06Z
dc.date.available2022-06-23T04:20:06Z
dc.date.issued2017-01-01
dc.identifier.citationChemoenzymatic 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.issn14770520
dc.identifier.urihttps://hdl.handle.net/20.500.13015/5342
dc.identifier.urihttps://doi.org/10.1039/C6OB02603F
dc.descriptionOrganic and Biomolecular Chemistry, 15, 1222–1227
dc.descriptionNote : 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.abstractA 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.sponsorshipNational Institutes of Health
dc.languageen_US
dc.language.isoENG
dc.publisherRoyal Society of Chemistry
dc.relation.ispartofThe Linhardt Research Labs Online Collection
dc.relation.ispartofRensselaer Polytechnic Institute, Troy, NY
dc.relation.ispartofOrganic and Biomolecular Chemistry
dc.relation.urihttps://harc.rpi.edu/
dc.subjectBiology
dc.subjectChemistry and chemical biology
dc.subjectChemical and biological engineering
dc.subjectBiomedical engineering
dc.titleChemoenzymatic synthesis of unmodified heparin oligosaccharides: Cleavage of p-nitrophenyl glucuronide by alkaline and Smith degradation
dc.typeArticle
dcterms.accessRightsA full text version is available in DSpace@RPI
dcterms.isPartOfJournal
dcterms.isVersionOfhttps://doi.org/10.1039/C6OB02603F
dc.rights.holderIn 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.identifierhttps://orcid.org/0000-0003-2219-5833
dc.relation.departmentThe Linhardt Research Labs.
dc.relation.departmentThe Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)
rpi.description.pages1222-1227
rpi.description.volume15


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