title: Total synthesis of the α-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 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. The dodecamer sugar is a consensus sequence incorporating the key features associated with human glycoproteins.
authors.affiliation: Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10065, USA.
authors.forename: Baptiste
authors.initials: B
authors.lastname: Aussedat
authors.forename: Bernhard
authors.initials: B
authors.lastname: Fasching
authors.forename: Eric
authors.initials: E
authors.lastname: Johnston
authors.forename: Neeraj
authors.initials: N
authors.lastname: Sane
authors.forename: Pavel
authors.initials: P
authors.lastname: Nagorny
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky
mesh_terms: D000595:Amino Acid Sequence; D060326:Chemistry Techniques, Synthetic; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D043373:Follicle Stimulating Hormone, Human / Q000138:chemical synthesis* / Q000737:chemistry; D015292:Glycoprotein Hormones, alpha Subunit / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006801:Humans; D008958:Models, Molecular; D008969:Molecular Sequence Data
chemical_list: D004187:Disaccharides; D043373:Follicle Stimulating Hormone, Human; D015292:Glycoprotein Hormones, alpha Subunit; C032438:chitobiose