851787-54-7

Upstream product

• 92-66-0 4-bromo-1,1'-biphenyl 
• 3315-91-1 4-biphenylylmagnesium bromide 
• 14233-64-8 (3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one 
• 851787-50-3 Imidazole-1-carbothioic acid O-((2S,3S,3aR,9aR)-2-biphenyl-4-yl-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl) ester 
• 851787-48-9 (2S,3S,4R,5R)-2-([1,1'-biphenyl]-4-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran 
• 851787-49-0 (2S,3S,3aS,9aR)-2-Biphenyl-4-yl-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-ol 
• 851787-52-5 (2R,3aS,9aR)-2-Biphenyl-4-yl-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacyclooctene 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 851787-53-6 (2R,3S,5R)-5-Biphenyl-4-yl-2-hydroxymethyl-tetrahydro-furan-3-ol 

Relevant academic research and scientific papers

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.

Polycyclic aromatic DNA-base surrogates: High-affinity binding to an adenine-specific base-flipping DNA methyltransferase

Filling the hole is a strategy that confers high-affinity DNA binding to the M·TaqI DNA methyltransferase. Aromatic base surrogates (e.g. pyrene, red in picture) were introduced into DNA by means of organocuprate-mediated C-glycosylations. A new competitive binding assay revealed that DNA with aromatic base surrogates placed opposite to the target base binds to M·TaqI with up to 400-fold-enhanced affinity.