367518-77-2

Upstream product

• 1007-99-4 2-amino-6-chloro-5-nitro-3H-pyrimidine-4-one 
• 418760-15-3 2-deoxy-α,β-D-erythropentofuranosyl azide 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 367518-76-1 2-deoxy-3-O-dimethoxytrityl-5-O-tert-butyl(dimethyl)silyl-α,β-D-erythropentofuranosyl azide 
• 367518-85-2 (2R,3S)-5-Azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-ol 
• 367518-84-1 3,5-di-O-acetyl-2-deoxy-D-ribofuranosyl azide 
• 4594-52-9 1,3,5-tri-O-acetyl-2-deoxyribose 

Downstream Products

• 367518-79-4 C₅₅H₆₆N₇O₁₇PSi 
• 367518-81-8 6-[2’-deoxy-3’-O-dimethoxytrityl-α-D-ribofuranose-1’-yl]amino-5-nitro-2-(phenoxylacetyl)amino-3H-pyrimidine-4-one 
• 367518-78-3 6-[2’-deoxy-3’-O-dimethoxytrityl-β-D-ribofuranose-1’-yl]amino-5-nitro-2-(phenoxylacetyl)amino-3H-pyrimidine-4-one 
• 367518-86-3 6-[2’-deoxy-3’-O-dimethoxytrityl-5’-O-tert-butyl(dimethyl)silyl-α,β-D-ribofuranose-1’-yl]amino-5-nitro-2-(phenoxylacetyl)amino-3H-pyrimidine-4-one 

Relevant academic research and scientific papers

SOLID-PHASE SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING N6-(2-DEOXY-ALPHA,BETA-DERYTHROPENTOFURANOSYL)-2,6-DIAMINO-4-HYDROXY-5-FORMAMIDOPYRIMIDINE (Fapy.dG)

A strategy using reverse phosphoramidites for synthesizing oligonucleotides containing Fapy.dG is disclosed.

Synthesis of Oligonucleotides Containing the N6-(2-Deoxy-α,β-d-erythropentofuranosyl)-2,6-diamino-4-hydroxy-5-formamidopyrimidine (Fapy?dG) Oxidative Damage Product Derived from 2′-Deoxyguanosine

N6-(2-Deoxy-α,β-d-erythropentofuranosyl)-2,6-diamino-4-hydroxy-5-formamidopyrimidine (Fapy?dG) is a major DNA lesion produced from 2′-deoxyguanosine under oxidizing conditions. Fapy?dG is produced from a common intermediate that leads to 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-OxodGuo), and in greater quantities in cells. The impact of Fapy?dG on DNA structure and function is much less well understood than that of 8-OxodGuo. This is largely due to the significantly greater difficulty in synthesizing oligonucleotides containing Fapy?dG than 8-OxodGuo. We describe a synthetic approach for preparing oligonucleotides containing Fapy?dG that will facilitate intensive studies of this lesion in DNA. A variety of oligonucleotides as long as 30 nucleotides are synthesized. We anticipate that the chemistry described herein will provide an impetus for a wide range of studies involving Fapy?dG.

Synthesis and characterization of oligodeoxynucleotides containing formamidopyrimidine lesions and nonhydrolyzable analogues

Oligodeoxynucleotides containing formamidopyrimidine lesions and C-nucleoside analogues at defined sites were prepared by solid-phase synthesis and in some cases enzymatic ligation. Formamidopyrimidine lesions were introduced as dinucleotides to prevent r