title: An aminooxy-functionalized non-nucleosidic phosphoramidite for the construction of multiantennary oligonucleotide glycoconjugates on a solid support.
abstract: In this unit, a method is described that allows construction of multiantennary oligonucleotide glycoconjugates on a solid support. A bis(hydroxymethyl)malondiamide-based phosphoramidite that contains two phthaloyl-protected aminooxy groups compatible with normal chain assembly is prepared. The aminooxy functions can be deblocked with a hydrazinium acetate treatment and subsequently oximated on-support with fully acetylated 4-oxobutyl alpha-D-mannopyranoside. The resulting reagent is then used to prepare a conjugate containing two non-nucleosidic building blocks (i.e., four alpha-D-mannopyranosyl units) close to the 5' terminus of the oligonucleotide.
authors.affiliation: University of Turku, Turku, Finland.
authors.forename: Johanna
authors.initials: J
authors.lastname: Katajisto
authors.forename: Pasi
authors.initials: P
authors.lastname: Virta
authors.forename: Harri
authors.initials: H
authors.lastname: Lönnberg
mesh_terms: D002851:Chromatography, High Pressure Liquid; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D008358:Mannose / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*
chemical_list: D006001:Glycoconjugates; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D008358:Mannose