169243-52-1

Upstream product

• 59-14-3 5-bromo-2'-deoxyuridine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 169243-63-4 [2-(1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl ester 
• 169243-64-5 {2-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-phenyl}-carbamic acid tert-butyl ester 
• 114552-32-8 N-tert-butoxycarbonyl-2-trimethylstannylaniline 
• 54-42-2 5-Iodo-2'-deoxyuridine 

Relevant academic research and scientific papers

A Carbazole-Derived Nitroxide That Is an Analogue of Cytidine: A Rigid Spin Label for DNA and RNA

A variety of semirigid and rigid spin labels comprise a valuable arsenal for measurements of biomolecular structures and dynamics by electron paramagnetic resonance (EPR) spectroscopy. Here, we report the synthesis and characterization of rigid spin labels ? and ?m for DNA and RNA, respectively, that are carbazole-derived nitroxides and analogues of cytidine. ? and ?m were converted to their phosphoramidites and used for their incorporation into oligonucleotides by solid-phase synthesis. Analysis of ? and ?m by single-crystal X-ray crystallography verified their identity and showed little deviation from planarity of the nucleobase. Analysis of the continuous-wave (CW) EPR spectra of the spin-labeled DNA and RNA duplexes confirmed their incorporation into the nucleic acids and the line-shape was characteristic of rigid spin labels. Circular dichroism (CD) and thermal denaturation studies of the ?-labeled DNAs and ?m-labeled RNAs indicated that the labels are nonperturbing of duplex structure.

Hybridization properties of oligonucleotides bearing a tricyclic 2'- deoxycytidine analog based on a carbazole ring system

A tricyclic carbazole-like 2'-deoxycytidine analog has been synthesized via a Stille biaryl coupling on 5-iodo-2'-deoxyuridine followed by cyclization. The carbazole nucleoside was incorporated in oligonucleotides (ONs) and shown to pair specifically with guanine. Duplexes resulting from the carbazole analog ONs and complementary RNA have elevated T(m)s especially when the carbazole nucleosides are clustered.