title: Preparation of a disulfide-linked precipitative soluble support for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3´-(2-chlorophenylphosphate) building blocks.
abstract: The preparation of a disulfide-tethered precipitative soluble support and its use for solution-phase synthesis of trimeric oligodeoxyribonucleotide 3´-(2-chlorophenylphosphate) building blocks is described. To obtain the building blocks, N-acyl protected 2´-deoxy-5´-O-(4,4´-dimethoxytrityl)ribonucleosides were phosphorylated with bis(benzotriazol-1-yl) 2-chlorophenyl phosphate. The "outdated" phosphotriester strategy, based on coupling of P(V) building blocks in conjunction with quantitative precipitation of the oligodeoxyribonucleotide with MeOH is applied. Subsequent release of the resulting phosphate and base-protected oligodeoxyribonucleotide trimer 3'-pTpdC(Bz)pdG(ibu)-5' as its 3'-(2-chlorophenyl phosphate) was achieved by reductive cleavage of the disulfide bond.
authors.affiliation: Department of Chemistry, University of Turku, FIN-20014 Turku, Finland ; current address: Rega Institute for Medical Research, Minderbroedersstraat 10, KU Leuven, 3000- Leuven, Belgium.
authors.forename: Amit M
authors.initials: AM
authors.lastname: Jabgunde
authors.affiliation: Department of Chemistry, University of Turku, FIN-20014 Turku, Finland.
authors.forename: Alejandro Gimenez
authors.initials: AG
authors.lastname: Molina
authors.affiliation: Department of Chemistry, University of Turku, FIN-20014 Turku, Finland.
authors.forename: Pasi
authors.initials: P
authors.lastname: Virta
authors.affiliation: Department of Chemistry, University of Turku, FIN-20014 Turku, Finland.
authors.forename: Harri
authors.initials: H
authors.lastname: Lönnberg
keywords: disulfide linker; oligodeoxyribonucleotides; phosphotriester chemistry; precipitation; soluble support