851787-55-8

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 377777-55-4 1β-(2,2'-bipyridin-5-yl)-1,2-dideoxy-D-ribofuranose 
• 14233-64-8 (3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one 
• 15862-19-8 5-bromo-2,2'-bipyridyl 
• 851787-51-4 Imidazole-1-carbothioic acid O-((2S,3S,3aR,9aR)-2-[2,2']bipyridinyl-5-yl-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl) ester 
• 377777-50-9 5-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-[2,2']bipyridinyl 
• 377777-53-2 (2S,3S,3aS,9aR)-2-[2,2']Bipyridinyl-5-yl-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 
• 377777-54-3 5-((2R,3aS,9aR)-5,5,7,7-Tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-[2,2']bipyridinyl 
• 160539-05-9 5-iodo-2,2'-bipyridine 

Relevant academic research and scientific papers

A stable DNA duplex containing a non-hydrogen-bonding and non-shape-complementary base couple: Interstrand stacking as the stability determining factor

The stabilizing effect of a dG:dC base-pair can also be imparted to a DNA duplex by a non-hydrogen- bonding, non-shape-complementary nucleoside analogue when interstrand stacking interactions come into play. This is the case, for example, with dBP, which

Bipyridyl- and biphenyl-DNA: A recognition motif based on interstrand aromatic stacking

The synthesis and incorporation into oligonucleotides of C-nucleosides containing the two aromatic, non-hydrogen-bonding nucleobase substitutes biphenyl (I) and bipyridyl (Y) are described. Their homo- and hetero-recognition properties in different sequential arrangements were then investigated via UV-melting curve analysis, gelmobility assays, CD- and NMR spectroscopy. An NMR analysis of a dodecamer duplex containing one biphenyl pair in the center, as well as CD data on duplexes with multiple insertions provide further evidence for the zipper-like interstrand stacking motif that we proposed earlier based on molecular modeling. UV-thermal melting experiments with duplexes containing one to up to seven I- or Y base pairs revealed a constant increase in Tm in the case of I and a constant decrease for Y. Mixed I/Y base pairs lead to stabilities in between the homoseries. Insertion of alternating I/abasic site- or Y/abasic site pairs strongly decreases the thermal stability of duplexes. Asymmetric distribution of I- or Y residues on either strand of the duplex were also investigated in this context. Duplexes with three natural base pairs at both ends and 50% of I pairs in the center are still readily formed, while duplexes with blunt ended I pairs tend to aggregate unspecifically. Duplexes with one natural overhang at the end of a I-I base pair tract can both aggregate or form ordered duplexes, depending on the nature of the natural bases in the overhang.