287980-23-8

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 55520-67-7 5-vinyl-2'-deoxyuridine 
• 117626-99-0 3'-O-Acetyl-2'-deoxy-5-ethynyluridine 
• 117626-97-8 5'-O-(4,4'-dimethoxytrityl)-5-(1-phenyl-1H-1,2,3-triazol-4-yl)-2'-deoxyuridine 
• 61135-33-9 2'-deoxy-5-ethynyluridine 
• 117626-98-9 3'-Acetyl-2'-deoxy-5-ethynyl-5'-(4,4'-dimethoxytrityl)uridine 

Downstream Products

• 117626-80-9 Sodium; {[(2R,3S,5R)-5-(2,4-dioxo-5-vinyl-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryl}-acetate 
• 287980-24-9 5′-O-(4,4′-dimethoxytrityl)-3′-O-[2-cyanoethoxy-(N,N-diisopropylamino)-phosphino]-5-vinyl-2′-deoxyuridine 

Relevant academic research and scientific papers

Chemoselective Modification of Vinyl DNA by Triazolinediones

A new method for the post-synthetic modification of nucleic acids was developed that involves mixing a phenyl triazolinedione (PTAD) derivative with DNA containing a vinyl nucleobase. The resulting reactions proceeded through step-wise mechanisms, giving either a formal [4+2] cycloaddition product, or, depending on the context of nucleobase, PTAD addition along with solvent trapping to give a secondary alcohol in water. Catalyst-free addition between PTAD and the terminal alkene of 5-vinyl-2′-deoxyuridine (VdU) was exceptionally fast, with a second-order rate constant of 2×103 m?1 s?1. PTAD derivatives selectively reacted with VdU-containing oligonucleotides in a conformation-selective manner, with higher yields observed for G-quadruplex versus duplex DNA. These results demonstrate a new strategy for copper-free bioconjugation of DNA that can potentially be used to probe nucleic acid conformations in cells.

Detection of methylcytosine by DNA photoligation via hydrophobic interaction of the alkyl group

We report the nonenzymatic detection of 5-methylcytosine by using template-directed photoligation through 5-vinyl-2′-deoxyuridine derivatives with high selectivity. In this paper, we propose a new detection method by using hydrophobic interaction. The photoligation yield of the 5-methylcytosine case was approximately 5.6-fold higher than that in the case of cytosine.

Template-directed reversible photocircularization of DNA via 5-vinyldeoxycytidine

An efficient and reversible template-directed photoligation of oligodeoxynucleotides (ODNs) using 5-vinyldeoxycytidine ((v)c) was described. When ODN containing (v)C at the 5' end was photoirradiated with ODN containing thymine at the 3' end in the presence of a template ODN, an efficient photoligation was observed. Reversible photopadlocking of a circular DNA by the photocircularization using (v)C was demonstrated. (C) 2000 Elsevier Science Ltd.

Synthesis and Antiviral Activity of Phosphonoacetic and Phosphonoformic Acid Esters of 5-Bromo-2'-deoxyuridine and Related Pyrimidine Nucleosides and Acyclonucleosides

Phosphonoacetic acid (PAA, 1) was coupled with various acyclonucleosides, 2'-deoxyuridines, cytidines, and arabinosyluracils, with 2,4,6-triisopropylbenzenesulfonyl chloride (TPS) or dicyclohexylcarbodiimide (DCCI) as condensing agents, to give a range of phosphonate esters.The carboxylic ester linkage of PAA to the 5'-position of 5-bromo-2'-deoxyuridine (BUdR, 3) was achieved via the mixed anhydride formed from (diethylphosphono)acetic acid and trifluoroacetic anhydride.Phosphonoformic acid (PFA, 2) was coupled with BUdR by using the DCCI method to give the phosphonate ester (59).Of these compounds only phosphonate esters in the 2'-deoxyuridine series showed significant activity against herpes simplex virus types 1 and 2.The BUdR-PAA derivative (7) and the BUdR-PFA derivative (59) were highly active, especially the latter, which was more active than the parent nucleoside BUdR (3) against the type 2 virus.The active compounds may exert their effects by extracellular or intracellular hydrolysis to the corresponding antiviral agents, but an intrinsic component of antiviral activity may also be involved.