255723-76-3

Upstream product

• 23669-79-6 DMT-dU 
• 6046-63-5 1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-chlorouracil 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 50-90-8 5-chloro-2'-deoxyuridine 

Downstream Products

• 1424271-75-9 5'-O-dimethoxytrityl-5-chloro-2'-deoxyuridine, 3'-[(2-cyanoethyl)(N,N-diisopropyl)]phosphoramidite 

Relevant academic research and scientific papers

Thermally reversible and irreversible interstrand photocrosslinking of 5-chloro-2′-deoxy-4-Thiouridine modified DNA oligonucleotides

We describe highly efficient interstrand photocrosslinking of a DNA duplex containing 5-chloro-2′-deoxy-4-Thiouridine (ClSdU) in one strand, proceeding via a two-step photochemical cascade, involving the formation of a thermally reversible crosslink between ClSdU and thymidine in the target strand and its subsequent conversion to a thermally stable fluorescent crosslink. These results show that ClSdU has great potential to be a valuable DNA photo-crosslinking reagent for chemical biology applications.

Inhibition of human thymidine phosphorylase by conformationally constrained pyrimidine nucleoside phosphonic acids and their "open-structure" isosteres

A series of conformationally constrained uridine-based nucleoside phosphonic acids containing annealed 1,3-dioxolane and 1,4-dioxane rings and their "open-structure" isosteres were synthesized and evaluated as potential multisubstrate-like inhibitors of t

Structure, stability and function of 5-chlorouracil modified A:U and G:U base pairs

The thymine analog 5-chlorouridine, first reported in the 1950s as anti-tumor agent, is known as an effective mutagen, clastogen and toxicant as well as an effective inducer of sister-chromatid exchange. Recently, the first microorganism with a chemically different genome was reported; the selected Escherichia coli strain relies on the four building blocks 5-chloro-2′- deoxyuridine (ClU), A, C and G instead of the standard T, A, C, G alphabet [Marlie re, P., Patrouix, J., Doering, V., Herdewijn, P., Tricot, S., Cruveiller, S., Bouzon, M. and Mutzel, R. (2011) Chemical evolution of a bacterium's genome. Angew. Chem. Int. Ed., 50, 7109-7114]. The residual fraction of T in the DNA of adapted bacteria was a massive number of mutations, including >1500 A to G or G to A transitions in a culture. The former is most likely due to wobble base pairing between ClU and G, which may be more common for ClU than T. To identify potential changes in the geometries of base pairs and duplexes as a result of replacement of T by ClU, we determined four crystal structures of a B-form DNA dodecamer duplex containing ClU:A or ClU:G base pairs. The structures reveal nearly identical geometries of these pairs compared with T:A or T:G, respectively, and no consequences for stability and cleavage by an endonuclease (EcoRI). The lack of significant changes in the geometry of ClU:A and ClU:G base pairs relative to the corresponding native pairs is consistent with the sustained unlimited self-reproduction of E. coli strains with virtually complete T→ClU genome substitution.