196872-67-0

Basic information

• Product Name: 1-[2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl]anthra[1,2-g]pteridine-2,4(1H,3H)-dione
• CAS NO: 196872-67-0
• Molecular Weight: 666.69
• Mol File: 196872-67-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-[2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl]anthra[1,2-g]pteridine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl]anthra[1,2-g]pteridine-2,4(1H,3H)-dione(196872-67-0)
• EPA Substance Registry System: 1-[2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-ribofuranosyl]anthra[1,2-g]pteridine-2,4(1H,3H)-dione(196872-67-0)

Safety Data

• Hazardous Substances Data: 196872-67-0(Hazardous Substances Data)

Upstream product

• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 3601-89-6 Hoffer's chlorosugar 
• 196872-60-3 4H-2,4,5,14-Tetraaza-pentaphene-1,3-dione 
• 613-13-8 2-aminoanthracene 

Downstream Products

• 196872-77-2 4-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-4H-2,4,5,14-tetraaza-pentaphene-1,3-dione 

Relevant articles and documents

Nucleotides. Part LIV. Synthesis of condensed N1-(2'-deoxy-β-D- ribofuranosyl)lumazines, new fluorescent building blocks in oligonucleotide synthesis

Various condensed areno[g]lumazine derivatives 2, 3, and 5-7 were synthesized as new fluorescent aglycones for glycosylation reactions with 2- deoxy-3,5-di-O-(p-toluoyl)-α/β-D-erythro-pentofuranosyl chloride (10) to form, in a Hilbert-Johnson-Birkofer reaction, the corresponding N1-(2'- deoxyribonucleosides) 15-21. The β-D-anomers 15, 17, 19, and 21 were deblocked to 24-27 and, together with N1-(2'-deoxy-β-D- ribofuranosyl)lumazine (22) and its 6,7-diphenyl derivative 23, dimethoxytritylated in 5'-position to 28-33. These intermediates were then converted into the 3'-(2-cyanoethyl diisopropylphosphoramidites) 34-39 which function as monomeric building block in oligonucleotide syntheses as well as into the 3'-(hydrogen succinates) 40-45 which can be used for coupling with the solid-support material. A series of lumazine-modified oligonucleotides were synthesized and the influence of the new nucleobases on the stability of duplex formation studied by measuring the T(m) values in comparison to model sequences. A substantial increase in the T(m) is observed on introduction of areno[g]lumazine moieties in the oligonucleotide chain stabilizing obviously the helical structures by improved stacking effects. Stabilization is strongly dependent on the site of the modified nucleobase in the chain.