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Total synthesis of the ?-subunit of human glycoprotein hormones: toward fully synthetic homogeneous human follicle-stimulating hormone.

ABSTRACT: Described herein is the first total chemical synthesis of the unique ?-subunit of the human glycoprotein hormone (?-hGPH). Unlike the biologically derived glycoprotein hormones, which are isolated as highly complex mixtures of glycoforms, ?-hGPH obtained by chemical synthesis contains discrete homogeneous glycoforms. Two such systems have been prepared. One contains the disaccharide chitobiose at the natural N-glycosylation sites. The other contains dodecamer oligosaccharides at these same sites. The dodecamer sugar is a consensus sequence incorporating the key features associated with human glycoproteins.

SUBMITTER: Aussedat B

PROVIDER: S-EPMC3288947 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

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Total synthesis of the α-subunit of human glycoprotein hormones: toward fully synthetic homogeneous human follicle-stimulating hormone.

Aussedat Baptiste B Fasching Bernhard B Johnston Eric E Sane Neeraj N Nagorny Pavel P Danishefsky Samuel J SJ

Journal of the American Chemical Society 20120206 7

Described herein is the first total chemical synthesis of the unique α-subunit of the human glycoprotein hormone (α-hGPH). Unlike the biologically derived glycoprotein hormones, which are isolated as highly complex mixtures of glycoforms, α-hGPH obtained by chemical synthesis contains discrete homogeneous glycoforms. Two such systems have been prepared. One contains the disaccharide chitobiose at the natural N-glycosylation sites. The other contains dodecamer oligosaccharides at these same sites ...[more]

PMID: 22280541

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Toward fully synthetic homogeneous beta-human follicle-stimulating hormone (beta-hFSH) with a biantennary N-linked dodecasaccharide. synthesis of beta-hFSH with chitobiose units at the natural linkage sites.

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