H. Salo et al., Aminooxy functionalized oligonucleotides: Preparation, on-support derivatization, and postsynthetic attachment to polymer support, BIOCONJ CHE, 10(5), 1999, pp. 815-823
Three novel phosphoramidites, each bearing a phthaloyl-protected aminooxy t
ail, were prepared and applied in automated oligonucleotide synthesis. Afte
r chain assembly, the phthaloyl protection was removed with hydrazinium ace
tate. Normal succinyl linker turned to be stable under these conditions, an
d hence the support-bound oligonucleotide could be converted to a pyrene ox
ime conjugates by reacting with pyrene carbaldehyde or cis-retinal. Standar
d ammonolytic deprotection then released the deprotected conjugate in solut
ion. Alternatively, the crude aminooxy-tethered oligonucleotide was immobil
ized to microscopic polymer particles by reacting the aminooxy function wit
h the particle-bound aldehyde or epoxide groups. These immobilized oligonuc
eotides were shown to serve properly as probes in a mixed phase hybridizati
on assay.