Disulfide-tethered solid supports for synthesis of photoluminescent oligonucleotide conjugates: Hydrolytic stability and labeling on the support



: Salo H, Guzaev A, Lonnberg H

Publisher: AMER CHEMICAL SOC

: 1998

Bioconjugate Chemistry

BIOCONJUGATE CHEMISTRY

: BIOCONJUGATE CHEM

: 9

: 3

: 365

: 371

: 7

: 1043-1802

DOI: https://doi.org/10.1021/bc970194g


Several new disulfide-tethered solid supports (S1-S5) were synthesized, and their resistance against ammonolysis was tested. Among these supports, only the one bearing an N-[15-[(4,4'-dimethoxytrityl)oxy]-12,13-dithiapentadecanoyl] linker (S4b) tolerated ammonolysis and exhibited properties compatible with the oligonucleotide synthesis by phosphoramidite strategy. The applicability of this disulfide linker structure in postsynthetic oligonucleotide labeling on the support was demonstrated by introduction of two photoluminescent lanthanide chelates or two dansyl groups to the N-4-(6-aminohexyl) amino-modified cytosine residues at the 5' end of the oligonucleotide sequence. Subsequent release of the resulting conjugates as their 3'-phosphates was achieved by reductive cleavage of the disulfide bond and precipitation of the conjugate from the solution with ethanol. The fluorescently tagged oligomer obtained showed hybridization properties similar to those of oligonucleotides labeled in solution.



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