170236-36-9

Upstream product

• 23669-79-6 DMT-dU 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 951-78-0 2'-deoxyuridine 
• 117560-95-9 Methanesulfonic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 

Downstream Products

• 170236-33-6 3'-azido-N₄-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2',3'-dideoxycytidine 
• 184241-37-0 4-Amino-1-{(2R,4S,5S)-4-azido-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one 
• 158846-98-1 5'-O-dimethoxytrityl-3'-azido-2',3'-dideoxyuridine 

Relevant academic research and scientific papers

Synthesis of 3′-S-phosphorothiolate oligonucleotides for their potential use in RNA interference

The potency of RNA interference (RNAi) undoubtedly can be improved through chemical modifications to the small interfering RNAs (siRNA). By incorporation of the 3′-S-phosphorothiolate modification into strands of RNA, it is hoped that specific regions of a siRNA duplex can be stabilised to enhance the target binding affinity of a selected antisense strand into the activated RNA-induced silencing complex (RISC*). Oligonucleotides composed entirely of this modification are desirable so unconventional 5′ → 3′synthesis is investigated, with initial solution-phase testing proving successful. The phosphoroamidite monomer required for solid-phase synthesis has also been produced. Copyright Taylor & Francis Group, LLC.

Thermal stabilisation of RNA·RNA duplexes and G-quadruplexes by phosphorothiolate linkages

The effect of 3′-S-phosphorothiolate linkages on the stability of RNA·RNA duplexes and G-quadruplex structures has been studied. 3′-Thio-2′-deoxyuridine was incorporated into RNA duplexes and thermal melting studies revealed that the resulting 3′-S-phosph

PROCESS FOR PREPARING DISULPHIDES AND THIOSULPHINATES AND COMPOUNDS PREPARED

Process for preparing a compound of the formula (I) R1-S(O)x—S(O)yR2 in which R1 represents a molecular hydrocarbon radical which can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si and X, where X represents a halogen; R2, independently of R1, represents a carbon-containing group or a molecular hydrocarbon radical which can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si and X, where X represents a halogen, and x and y are selected from 0 and 1 in such a way that the sum of x and y is not more than 1, characterized in that a compound of formula (II) R1-S(O)x—R3-Si(R4)(R5)(R6) in which R3 represents a hydrocarbon chain of two carbon atoms, which is optionally unsaturated and/or substituted, and R4, R5 and R6, which are identical or different, each represent, independently of one another, a hydrocarbon group, is reacted with a compound of formula (VII) R2-S(O)y—X in which X represents a halogen, intermediate compounds, and compounds prepared.

Anti-retroviral and cytostatic activity of 2′,3′-dideoxyribonucleoside 3′-disulfides

Herein, we report the synthesis, antiviral and cytostatic effects of nucleosides bearing a 3′-disulfide function as prodrugs of potentially active 3′-mercaptonucleotides. The lack of the anti-HIV effects in mutant CEM/TK-cells for most of the thymidine disulfides suggests that a phosphorylation step involving thymidine kinase is necessary for the eventual antiviral activity of the thymidine nucleosides. The comparable anti-HIV activities of most of the disulfides and their rapid reduction in CEM cell extracts imply an inhibitory effect of the 2′,3′-dideoxy-3′-mercaptothymidine 5′-triphosphate metabolite. The cytostatic effects of the disulfides in CEM/0 and Molt4/C8 cells appeared to be strongly dependent on the nature of the non-nucleosidic disulfide moiety and were decreased in preserving the anti-retroviral activity.

New carbamate supports for the preparation of 3'-amino-modified oligonucleotides

A novel approach for the preparation of oligonucleotides carrying amino groups at the 3'-end is described. Several CPG supports having aminoalkyl groups and 3'-amino-2',3'-dideoxynucleosides linked through base-labile carbamate linkages such as 2-(2- nitrophenyl)ethoxycarbonyl and fluorenylmethoxycarbonyl were prepared using two different strategies. These supports are compatible to the standard solid phase phosphite-triester methodology and yield oligonucleotides containing amino groups at the 3'-end. Several properties of the 3'-amino oligonucleotides, such as nuclease resistance, hybridization, and preparation of oligonucleotide conjugates are discussed.