141076-17-7

Basic information

• Product Name: 5''-O-(DIMETHOXYTRITYL)-S6-(2,4-DINITROPHENYL)-N2-PHENYLACETYL-2''-DEOXYTHIOGUANOSINE
• Synonyms: 5''-O-(DIMETHOXYTRITYL)-S6-(2,4-DINITROPHENYL)-N2-PHENYLACETYL-2''-DEOXYTHIOGUANOSINE
• CAS NO: 141076-17-7
• Molecular Formula: C₄₅H₃₉N₇O₁₀S
• Molecular Weight: 869.91
• Mol File: 141076-17-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5''-O-(DIMETHOXYTRITYL)-S6-(2,4-DINITROPHENYL)-N2-PHENYLACETYL-2''-DEOXYTHIOGUANOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5''-O-(DIMETHOXYTRITYL)-S6-(2,4-DINITROPHENYL)-N2-PHENYLACETYL-2''-DEOXYTHIOGUANOSINE(141076-17-7)
• EPA Substance Registry System: 5''-O-(DIMETHOXYTRITYL)-S6-(2,4-DINITROPHENYL)-N2-PHENYLACETYL-2''-DEOXYTHIOGUANOSINE(141076-17-7)

Safety Data

• Hazardous Substances Data: 141076-17-7(Hazardous Substances Data)

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 141076-16-6 N²-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine 
• 869355-10-2 N²-phenylacetyl-2'-deoxy-6-thioguanosine 
• 99519-11-6 3',5'-diacetyl-N²-phenylacetyl-2'-deoxyguanosine 
• 141076-15-5 3',5'-diacetyl-N²-phenylacetyl-2'-deoxy-6-thioguanosine 
• 302584-91-4 3',5'-diacetyl-N₂-phenylacetyl-6-mesitylenesulphonyl-2'-deoxyguanosine 
• 120022-75-5 2,4,6-Trimethyl-benzenesulfonate1-[9-((2R,4S,5R)-4-acetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-2-phenylacetylamino-9H-purin-6-yl]-1-methyl-pyrrolidinium; 

Downstream Products

• 141076-12-2 5'-O-(4,4-dimethoxytriphenylmethyl)-N²-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine-3'-O-(2-cyanoethyl-N,N-diisopropylamino)-phosphoramidite 

Relevant articles and documents

Synthesis by post-synthetic substitution of oligomers containing guanine modified at the 6-position with S-, N-, O-derivatives

6-(2,4-dinitrophenyl)thioguanine phosphoramidite monomers with the 2-amino group of the base protected by either the isobutyryl or phenylacetyl group were incorporated into oligodeoxynucleotides with an automatic DNA synthesizer. N2-protection with the isobutyryl group was unsatisfactory because of the difficulty of removing it after synthesis of the oligemer. However, post-synthetic conversion of the N2-phenylacetyl protected 6-(2,4-dinitrophenyl)thioguanine gives oligomers containing 6-thioguanine, 2,6-diaminopurine, 2-amino-6-methylaminopurine, O6-methylguanine or guanine in high yield and purity. Potentially oligemers containing other labile functional groups at the 6-position could be produced by the procedure. DNA duplexes containing 6-thioguanine paired to cytosine had a markedly lower melting temperature (Tm) than counterparts containing G:C. However a DNA duplex containing 4-thiothymine paired to A had a Tm similar to that of a DNA duplex containing T:A. The distortion in DNA structure caused by 6-thioguanine may play a role in the biological effect of this compound.