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dc.contributor.authorHung, Shang-Chengen_US
dc.contributor.authorLu, Xin-Anen_US
dc.contributor.authorLee, Jinq-Chyien_US
dc.contributor.authorChang, Margaret Dah-Tsyren_US
dc.contributor.authorFang, Shun-lungen_US
dc.contributor.authorFan, Tan-chien_US
dc.contributor.authorZulueta, Medel Manuel L.en_US
dc.contributor.authorZhong, Yong-Qingen_US
dc.date.accessioned2014-12-08T15:21:34Z-
dc.date.available2014-12-08T15:21:34Z-
dc.date.issued2012en_US
dc.identifier.issn1477-0520en_US
dc.identifier.urihttp://hdl.handle.net/11536/15327-
dc.identifier.urihttp://dx.doi.org/10.1039/c1ob06415ken_US
dc.description.abstractA convenient route for the synthesis of heparin oligosaccharides involving regioselective protection of D-glucosamine and a concise preparation of rare L-ido sugars from diacetone alpha-D-glucose is described. Stereoselective coupling of a D-glucosamine-derived trichloroacetimidate with a 1,6-anhydro-beta-L-idopyranosyl 4-alcohol gave the desired a-linked disaccharide, which was used as repeating unit for dual chain elongation and termination. Stepwise assembly from the reducing to the non-reducing end with a D-glucosamine-derived monosaccharide as starting unit furnished the oligosaccharide skeletons having different chain lengths. A series of functional group transformations afforded the expected heparin oligosaccharides with 3, 5 and 7 sugar units. Interaction of these oligosaccharides with eosinophil-derived neurotoxin (EDN), a cationic ribonuclease and a mediator produced by human eosinophils, was further investigated. The results revealed that at 5 mu g mL(-1), the heptasaccharide has sufficiently strong interference to block EDN binding to Beas-2B cells. The tri- and pentasaccharides have moderate inhibitory properties at 50 mu g mL(-1) concentration, but no inhibition has been observed at 10 mu g mL(-1). The IC(50) values of the tri-, penta- and heptasaccharides are 69.4, 47.2 and 0.225 mu g mL(-1), respectively.en_US
dc.language.isoen_USen_US
dc.titleSynthesis of heparin oligosaccharides and their interaction with eosinophil-derived neurotoxinen_US
dc.typeArticleen_US
dc.identifier.doi10.1039/c1ob06415ken_US
dc.identifier.journalORGANIC & BIOMOLECULAR CHEMISTRYen_US
dc.citation.volume10en_US
dc.citation.issue4en_US
dc.citation.spage760en_US
dc.citation.epage772en_US
dc.contributor.department應用化學系zh_TW
dc.contributor.departmentDepartment of Applied Chemistryen_US
dc.identifier.wosnumberWOS:000298751900011-
dc.citation.woscount18-
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