183194-53-8

Upstream product

• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 204929-06-6 2-amino-6-methyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidine 
• 204929-11-3 (2R,3S,5R)-5-(2-Amino-4-methoxy-6-methyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol 
• 183194-50-5 2-Amino-7-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-methyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 
• 62981-82-2 2-amino-6-methyl-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 183194-52-7 N-[7-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-methyl-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl]-isobutyramide 

Relevant academic research and scientific papers

7-Deazapurine Oligodeoxyribonucleotides: The Effects of 7-Deaza-8-methylguanine on DNA Structure and Stability

Oligodeoxyribonucleotides containing 7-deaza-2′-deoxy-8-methylguanosine (m8c7Gd; 2b) were prepared. For this purpose, the phosphonate 3a and the phosphoramidite 3b were synthesized and employed in solidphase oligodeoxyribonucleotide synthesis. The structures and the thermodynamic data of duplex formation of oligodeoxyribonucleotides containing 2b were investigated by temperature-dependent CD and UV spectra and compared with those containing 7-deaza-2′-deoxy-7-methylguanosine (m7c7Gd) or 7-deaza-2′-deoxy-guanosine (c7Gd; 2a). In general, compound 2b reduces the duplex stability. In case of the sequence d(m8c7G-C)4 (18), the B → Z transition was facilitated by the incorporation of 2b. Moreover, a single 7-deaza-8-methylguanine residue present in an oligodeoxyribonucleotide tract of guanine residues destabilizes the dG quadruplex significantly. This destabilization is more pronounced than in the case of 7-deazaguanine or 7-deaza-7-methyl-guanine.

Oligonucleotides containing 7- Or 8-methyl-7-deazaguanine: Steric requirements of major groove substituents on the DNA structure

Methyl groups in alternating octanucleotides containing 7-methyl-7-deazaguanine and cytosine have steric freedom and maintain the B-DNA structure, whereas the isomeric 8-methyl-7-deazaguanine causes a B-Z transition.