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 Journal Article

   

Authors:	Nagorny, P.; Fasching, B.; Li, X.; Chen, G.; Aussedat, B.; Danishefsky, S. J.
Article Title:	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
Abstract:	A 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.
Keywords:	unclassified drug; validity; chemical structure; glycoproteins; chemical reaction; n-linked; sialic acids; chitobiose; convergent synthesis; follicle stimulating hormone; functionalized; glycoprotein hormones; glycosidations; glycosylated; model system; n-linked glycans; side chains; tetrasaccharides; carboxylic acids; hormones; beta follicle stimulating hormone; carbohydrate derivative; dodecasaccharide; follitropin; tetrasaccharide; chemical bond; glycosidation; hormone synthesis
Journal Title:	Journal of the American Chemical Society
Volume:	131
Issue:	16
ISSN:	0002-7863
Publisher:	American Chemical Society
Date Published:	2009-04-29
Start Page:	5792
End Page:	5799
Language:	English
DOI:	10.1021/ja809554x
PROVIDER:	scopus
PMCID:	PMC2756579
PUBMED:	19341309
DOI/URL:	http://www.scopus.com/inward/record.url?eid=2-s2.0-70149089001&partnerID=40&md5=e25e776a2685630b5c57b9f94c4ae5e5
Notes:	--- - "Cited By (since 1996): 13" - "Export Date: 30 November 2010" - "CODEN: JACSA" - "Source: Scopus"

https://synapse.mskcc.org/synapse/works/has_related_data_chk/1112