127088-91-9Relevant academic research and scientific papers
Solution phase synthesis of dithymidine phosphorodithioate using new S- protecting groups in combination with a chemoselective coupling reagent (PyNOP)
Kehler, Jan,Pueschl, Ask,Dahl, Otto
, p. 23 - 32 (2007/10/03)
A method for the synthesis of O-thymidin-3'-yl S-alkyl dithiophosphate monomers 1 with different S-protecting groups has been developed. These have been used for solution phase synthesis of dithymidine phosphorodithioate by a new phosphotriester method. C
Synthesis of deoxydinucleoside phosphorodithioates
Brill, Wolfgang K.-D.,Nielsen, John,Caruthers, Marvin H.
, p. 3972 - 3980 (2007/10/02)
The synthesis of a new class of DNA analogues called phosphorodithioate DNA is described. This analogue, which has a deoxynucleoside-OPS2O-deoxynucleoside internucleotide linkage, is isosteric and isopolar with the normal phosphodiester, inert toward nucleases, and potentially useful for a large number of biochemical and biological applications. Two methods are described for synthesizing this derivative. One route begins by condensing a deoxynucleoside phosphorodiamidite with a second appropriately protected deoxynucleoside to yield a deoxydinucleoside phosphoramidite. Sulfhydrolysis with H2S generates the H-phosphonothioate, which upon oxidation with sulfur yields the deoxydinucleoside phosphorodithioate. Alternatively, sequential treatment of the deoxydinucleoside phosphoramidite with a mercaptan and sulfur yields the deoxydinucleoside phosphorodithioate triester. These deoxydinucleotides in protected form can then be used to introduce the dithioate internucleotide linkage into DNA. The second route for generating dithioate DNA uses deoxynucleoside phosphorothioamidites. Two derivatives, the deoxynucleoside 3′-N,N-dimetnyl- or 3′-(N,N-tetramethylenephosphorothioamidite), were found to be especially attractive synthons as they could be prepared in stable form via a one-flask synthesis procedure and used to form the deoxydinucleoside thiophosphite rapidly (1-2 min with tetrazole as activator) in high yield. Subsequent oxidation with sulfur generates the completely protected phosphorodithioate linkage.
Synthesis of oligonucleotide phosphorodithioates
Beaton,Brill,Grandas,Ma,Nielsen,Yau,Caruthers
, p. 2377 - 2388 (2007/10/02)
The synthesis of DNA containing sulfur at the two nonbonding internucleotide valencies is reported. Several different routes using either tervalent or pentavalent mononucleotide synthons are described.
Oxidative and nonoxidative formation of internucleotide linkages
Brill,Yau,Caruthers
, p. 6621 - 6624 (2007/10/02)
Activation of nucleoside 3'-hydrogenphosphonodithioates with iodine in the presence of nucleosides and amines yields dinucleoside phosphorodithioates and nucleoside phosphorodithioamidates, respectively. Similar activation of nucleoside 3'-methylphosphono
Deoxyribonucleoside Phosphorodithioates. Preparation of Dinucleoside Phosphorodithioates from Nucleoside Thiophosphoramidites
Dahl, Bjarne H.,Bjergarde, Kirsten,Sommer, Vibeke B.,Dahl, Otto
, p. 896 - 901 (2007/10/02)
A series of protected thymidine thiophosphoramidites have been prepared and their properties evaluated.Although less reactive than phosphoramidites, thiophosphoramidites with small N-substituents (methyl) are useful synthons for the preparation of nucleoside phosphorodithioates, as demonstrated by the preparation of a thymidine dimer.The coupling reactions are not as clean as those of the analogous phosphoramidites since the alkylthio group is somewhat labile.
