Automated synthesis of a protected N-linked glycoprotein core pentasaccharide.
[structure: see text] Described is the first automated solid-phase synthesis of the core N-linked pentasaccharide, common to all N-linked glycoproteins via stepwise assembly from mono- and disaccharide building blocks. The challenging beta-mannosidic linkage was incorporated by the inclusion of a disaccharide trichloroacetimidate. This automated synthesis provides rapid access to an oligosaccharide common to an entire class of glycoconjugates.
Ratner
Daniel M
DM
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Swanson
Erika R
ER
Seeberger
Peter H
PH
D000081:Acetamides; D001331:Automation; D002240:Carbohydrate Sequence; D062845:Chloroacetates; D006023:Glycoproteins / Q000138:chemical synthesis* / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D014238:Trichloroacetic Acid / Q000737:chemistry
D000081:Acetamides; D062845:Chloroacetates; D006023:Glycoproteins; D009844:Oligosaccharides; D014238:Trichloroacetic Acid; C009528:trichloroacetamide