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Article: Toward fully synthetic homogeneous β -human Follicle-Stimulating hormone (β -hFSH) with a biantennary N-linked dodecasaccharide. synthesis of β -hFSH with chitobiose units at the natural linkage sites

TitleToward fully synthetic homogeneous β -human Follicle-Stimulating hormone (β -hFSH) with a biantennary N-linked dodecasaccharide. synthesis of β -hFSH with chitobiose units at the natural linkage sites
Authors
Issue Date2009
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html
Citation
Journal Of The American Chemical Society, 2009, v. 131 n. 16, p. 5792-5799 How to Cite?
AbstractA highly convergent synthesis of the sialic acid-rich biantennary N-linked glycan found in human glycoprotein hormones and its use in the synthesis of a fragment derived from the β -domain of human Follicle-Stimulating Hormone (hFSH) are described. The synthesis highlights the use of the Sinay radical glycosidation protocol for the simultaneous installation of both biantennary side-chains of the dodecasaccharide as well as the use of glycal chemistry to construct the tetrasaccharide core in an efficient manner. The synthetic glycan was used to prepare the glycosylated 20-27aa domain of the β -subunit of hFSH under a Lansbury aspartylation protocol. The proposed strategy for incorporating the prepared N-linked dodecasaccharide-containing 20-27aa domain into β -hFSH subunit was validated in the context of a model system, providing protected β -hFSH subunit functionalized with chitobiose at positions 7 and 24. © 2009 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/168402
ISSN
2015 Impact Factor: 13.038
2015 SCImago Journal Rankings: 7.123
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorNagorny, Pen_US
dc.contributor.authorFasching, Ben_US
dc.contributor.authorLi, Xen_US
dc.contributor.authorChen, Gen_US
dc.contributor.authorAussedat, Ben_US
dc.contributor.authorDanishefsky, SJen_US
dc.date.accessioned2012-10-08T03:18:31Z-
dc.date.available2012-10-08T03:18:31Z-
dc.date.issued2009en_US
dc.identifier.citationJournal Of The American Chemical Society, 2009, v. 131 n. 16, p. 5792-5799en_US
dc.identifier.issn0002-7863en_US
dc.identifier.urihttp://hdl.handle.net/10722/168402-
dc.description.abstractA highly convergent synthesis of the sialic acid-rich biantennary N-linked glycan found in human glycoprotein hormones and its use in the synthesis of a fragment derived from the β -domain of human Follicle-Stimulating Hormone (hFSH) are described. The synthesis highlights the use of the Sinay radical glycosidation protocol for the simultaneous installation of both biantennary side-chains of the dodecasaccharide as well as the use of glycal chemistry to construct the tetrasaccharide core in an efficient manner. The synthetic glycan was used to prepare the glycosylated 20-27aa domain of the β -subunit of hFSH under a Lansbury aspartylation protocol. The proposed strategy for incorporating the prepared N-linked dodecasaccharide-containing 20-27aa domain into β -hFSH subunit was validated in the context of a model system, providing protected β -hFSH subunit functionalized with chitobiose at positions 7 and 24. © 2009 American Chemical Society.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.htmlen_US
dc.relation.ispartofJournal of the American Chemical Societyen_US
dc.titleToward fully synthetic homogeneous β -human Follicle-Stimulating hormone (β -hFSH) with a biantennary N-linked dodecasaccharide. synthesis of β -hFSH with chitobiose units at the natural linkage sitesen_US
dc.typeArticleen_US
dc.identifier.emailLi, X:xuechenl@hku.hken_US
dc.identifier.authorityLi, X=rp00742en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/ja809554xen_US
dc.identifier.pmid19341309-
dc.identifier.scopuseid_2-s2.0-70149089001en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-70149089001&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume131en_US
dc.identifier.issue16en_US
dc.identifier.spage5792en_US
dc.identifier.epage5799en_US
dc.identifier.isiWOS:000265460200027-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridNagorny, P=35074640500en_US
dc.identifier.scopusauthoridFasching, B=14526909400en_US
dc.identifier.scopusauthoridLi, X=24168958800en_US
dc.identifier.scopusauthoridChen, G=9744566700en_US
dc.identifier.scopusauthoridAussedat, B=6505949882en_US
dc.identifier.scopusauthoridDanishefsky, SJ=7202925243en_US

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