1415304-21-0

Basic information

• Product Name: 5′-O-(4,4′-dimethoxytrityl)-N²-(dimethylformamidyl)-8-(2″-furyl)-2′-deoxyguanosine
• Synonyms: 5′-O-(4,4′-dimethoxytrityl)-N²-(dimethylformamidyl)-8-(2″-furyl)-2′-deoxyguanosine
• CAS NO: 1415304-21-0
• Molecular Weight: 690.756
• Mol File: 1415304-21-0.mol

Chemical Properties

• CAS DataBase Reference: 5′-O-(4,4′-dimethoxytrityl)-N²-(dimethylformamidyl)-8-(2″-furyl)-2′-deoxyguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 5′-O-(4,4′-dimethoxytrityl)-N²-(dimethylformamidyl)-8-(2″-furyl)-2′-deoxyguanosine(1415304-21-0)
• EPA Substance Registry System: 5′-O-(4,4′-dimethoxytrityl)-N²-(dimethylformamidyl)-8-(2″-furyl)-2′-deoxyguanosine(1415304-21-0)

Safety Data

• Hazardous Substances Data: 1415304-21-0(Hazardous Substances Data)

Upstream product

• 1061729-78-9 (2''-furyl)-2'-deoxyguansine 
• 1415304-20-9 N²-(dimethylformamidyl)-8-(2″-furyl)-2′-deoxyguansine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 13389-03-2 8-bromo-2'-deoxyguanosine 

Downstream Products

• 1415304-22-1 3′-O-[(2-cyanoethoxy)(diisopropylamino)phosphino]-5′-O-(4,4′-dimethoxytrityl)-N²-(dimethylformamidyl)-8-(2″-furyl)-2′-deoxyguanosine 

Relevant articles and documents

Utility of 5'-o-2,7-dimethylpixyl for solid-phase synthesis of oligonucleotides containing acid-sensitive 8-aryl-guanine adducts

To study the structural and biological impact of 8-aryl-2'-deoxyguanosine adducts, an efficient protocol is required to incorporate them site-specifically into oligonucleotide substrates. Traditional phosphoramidite chemistry using 5'- O-DMT protection can be limiting because 8-aryl-dG adducts suffer from greater rates of acid-catalyzed depurination than dG and are sensitive to the acidic deblock conditions required to remove the DMT group. Herein we show that the 5'-O-2,7- dimethylpixyl (DMPx) protecting group can be used to limit acid exposure and improve DNA synthesis efficiency for DNA substrates containing 8-aryl-dG adducts. Our studies focus on 8-aryl-dG adducts with 8-substituents consisting of furyl (FurdG), phenyl (PhdG), 4-cyanophenyl (CNPhdG), and quinolyl (QdG). These adducts differ in ring size and sensitivity to acid-promoted deglycosylation. A kinetic study for adduct hydrolysis in 0.1 M aqueous HCl determined that FurdG was the most acid-sensitive (55.2-fold > dG), while QdG was the most resistant (5.6-fold > dG). The most acid-sensitive FurdG was chosen for optimization of solid-phase DNA synthesis. Our studies show that the 5'-O-DMPx group can provide a 4-fold increase in yield compared to 5'- O-DMT for incorporation of FurdG into DNA substrates critical for determining adduct impact on DNA synthesis and repair.

C8-heteroaryl-2′-deoxyguanosine adducts as conformational fluorescent probes in the narl recognition sequence

The optical, redox, and electronic properties of C8-heteroaryl- 2′-deoxyguanosine (dG) adducts with C8-substituents consisting of furyl (FurdG), pyrrolyl (PyrdG), thienyl ( ThdG), benzofuryl (Bfu