145498-68-6Relevant academic research and scientific papers
The synthesis of di- and oligo(deoxyribonucleoside phosphorodithioates) by dithiaphospholane method
Okruszek,Sierzchala,Sochacki,Stec
, p. 7585 - 7588 (1992)
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.
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.
