145498-69-7Relevant academic research and scientific papers
Synthesis of Oligo(deoxyribonucleoside phosphorodithioate)s by the Dithiaphospholane Approach
Okruszek, Andrzej,Sierzchala, Agnieszka,Fearon, Karen L.,Stec, Wojciech J.
, p. 6998 - 7005 (2007/10/03)
A novel method of synthesis of oligo(deoxyribonucleoside phosphorodithioate)s (S2-ODNs), based on the ring-opening condensation of nucleoside 3'-O-(2-thiono-1,3,2-dithiaphospholane)s with 5'-O-deprotected nucleosi(ti)des in the presence of a strong organic base such as DBU, is presented.The process has been adapted to the requirements of automated solid-phase oligonucleotide synthesis with a relatively short condensation step (5 min) and reasonable step-yield (>95percent).N-Methylpyrrolidin-2-ylidenyl (Pya) was found to be the group of choice for the protection of reactive aminofunctions of nucleobases in nucleotide substrates.Sarcosine-containing linker (LCA CPG SAR) was employed due to its known resistance to cleavage by DBU.Several medium-size S2-ODNs were prepared by this approach.Their identity and purity was confirmed by means of 31P NMR, gel electrophoresis, and mass spectrometry.It has been demonstrated that, contrary to a recent report, S2-ODNs are not degraded by DNaseI.
The synthesis of di- and oligo(deoxyribonucleoside phosphorodithioates) by dithiaphospholane method
Okruszek,Sierzchala,Sochacki,Stec
, p. 7585 - 7588 (2007/10/02)
Four dinucleoside phosphorodithioates: T(PS2)T (1a), d(C(PS2)C) (1b), d(A(PS2)A) (1c) and d(G(PS2)G) (1d) were synthesized by reacting solid support-bound nucleosides with nucleoside 5'-O-DMT-3'-O-(2-thio-1,3,2-dithiaphospholanes) (2a-d) in the presence of DBU. Pyrimidine pentamers and decamers, free from phosphorothioate contamination, were obtained by this method.
