196925-91-4

Upstream product

• 693-02-7 hex-1-yne 
• 174462-92-1 N-(7-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-iodo-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl)-isobutyramide 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 196925-90-3 N-[5-Hex-1-ynyl-7-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-2-yl]-isobutyramide 
• 172163-62-1 7-iodo-7-deaza-2'-deoxyguanosine 
• 172163-63-2 2-Amino-5-hex-1-ynyl-7-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one 
• 174462-91-0 7-[2-deoxy-β-D-erythro-pentofuranosyl]-5-iodo-2-(isobutyrylamino)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one 

Relevant academic research and scientific papers

123. 7-Deazaguanine DNA: Oligonucleotides with Hydrophobic or Cationic Side Chains

The phosphoramidites 6b and 9 as well as the phosphonate 6a derived from 7-(hex-1-ynyl)- and 7-[5-(trifluoroacetamido)pent-1-ynyl]-substituted 7-deaza-2′-deoxyguanosines 1 and 10, respectively, were prepared (Scheme 1). They were employed in solid-phase oligodeoxynucleotide synthesis of the alternating octamers d(hxy7c7G-C)4 (12), d(C-hxy7c7G)4 (13), and d(npey7c7G-C)4 (15) as well as of other oligonucleotides (see 22-25; Table 2; hxy = hex-1-ynyl, npey = 5-aminopent-1-ynyl). The Tm values and the thermodynamic data of duplex formation were determined and correlated with the major-groove modification of the DNA fragments. A hexynyl side chain introduced into the 7-position of a 7-deazaguanine residue (see 1) was found to fit into the major groove without any protrusion. The incorporation of the (5-aminopent-1-ynyl)-modified 7-deaza-2′-deoxyguanosine 2 into single-stranded oligomers of the type 24 and 25 did not lead to change in duplex stability compared to the parent oligonucleotides. The self-complementary oligomer 15 with alternating npey7c7Gd (2) and dC units did not lead to a cooperative melting, either due to orientational disorder or interaction of the 5-aminopent-1-ynyl moiety with a base or with phosphate residues nearby or on the opposite strand.

Duplex stability of oligonucleotides containing 7-substituted 7-deaza- and 8-aza-7-deazapurine nucleosides

The synthesis of 7-substituted 7-deaza- and 8-aza-7-deazapurine 2'deoxyribonucleosides, their incorporation into oligonucleotides, and the stability of corresponding duplexes is described.