An aminooxy-functionalized non-nucleosidic phosphoramidite for the construction of multiantennary oligonucleotide glycoconjugates on a solid support.
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.
Katajisto
Johanna
J
University of Turku, Turku, Finland.
Virta
Pasi
P
Lönnberg
Harri
H
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*
D006001:Glycoconjugates; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D008358:Mannose