302584-91-4

Upstream product

• 773-64-8 2-mesitylenesulphonyl chloride 
• 99519-11-6 3',5'-diacetyl-N²-phenylacetyl-2'-deoxyguanosine 

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 
• 141076-17-7 N-[9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-(2,4-dinitro-phenylsulfanyl)-9H-purin-2-yl]-2-phenyl-acetamide 
• 141076-16-6 N²-phenylacetyl-2'-deoxy-6-(2,4-dinitrophenyl)thioguanosine 
• 141076-15-5 3',5'-diacetyl-N²-phenylacetyl-2'-deoxy-6-thioguanosine 
• 869355-10-2 N²-phenylacetyl-2'-deoxy-6-thioguanosine 
• 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; 

Relevant academic research and scientific papers

Synthesis and characterization of DNA containing O6-carboxymethylguanine

O6-Carboxymethylguanine was formed in DNA treated with N-nitrosoglycocholic acid and believed to be implicated in human gastrointestinal and colorectal tumour. An efficient method is presented here for synthesis of oligodeoxynucleotides containing O6-carboxy-methylguanine at pre-determined positions. The synthetic protocol also allows for production of oligomers containing O6-aminocarbonyl-methylguanine. These guanine-modified oligomers have been fully characterized and could provide a useful tool for biological studies of these modified bases. (C) 2000 Elsevier Science Ltd.

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.