229469-60-7

Upstream product

• 1392279-59-2 C₂₇H₂₄Cl₂O₅ 
• 1392279-55-8 C₂₆H₂₂Cl₂O₅ 
• 173327-56-5 3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose 
• 34371-14-7 2-deoxy-D-ribonolactone 
• 452-51-7 D-2-deoxyribose 
• 591-17-3 meta-bromotoluene 
• 169526-37-8 (6aR,9aS)-2,2,4,4-tetraisopropyltetrahydro-8H-furo[3,2-f ][1,3,5,2,4]trioxadisilocin-8-one 

Downstream Products

• 1396637-30-1 C₆H₁₅N*C₄₅H₄₉N₂O₁₃P 
• 1392279-50-3 C₂₂H₂₉N₂O₁₀P 
• 1392279-58-1 C₄₅H₄₉N₂O₁₃P 
• 1392279-57-0 C₁₄H₁₈O₄ 
• 1392279-56-9 C₃₅H₃₆O₆ 
• 805240-85-1 1',2'-dideoxy-β-1'-(3-methylphenyl)-5'-O-(4,4'-dimethoxytrityl)-D-ribofuranose 

Relevant academic research and scientific papers

Expanding the horizon of the thymine Isostere biochemistry: Unique cyclobutane dimers formed by photoreaction between a thymine and a toluene residue in the dinucleotide framework

Substituted toluenyl groups are considered as close isosteres of the thymine residue. They can be recognized by DNA polymerases as if they were thymine. These toluene derivatives are generally inert toward radical additions, including the [2+2] photocycloadditions, due to the stable structure of the aromatic ring and are usually used as solvents for radical reactions. Surprisingly, after incorporating toluene into the dinucleotide framework, we found that the UV excited thymine residue readily dimerizes with the toluenyl moiety through a [2+2] photoaddition reaction. Furthermore, the reaction site on the toluenyl moiety is not the C5=C6 bond, as commonly observed in cyclobutane pyrimidine dimers, but the C4=C5 or C3=C4 instead. Such a reaction pattern suggests that in the stacked structure, it is one of these bonds, not the C5=C6, that is close to the thymine C5=C6 bond. A similar structural feature is found in DNA duplex with a thymine replaced by a 2,4-difluorotoluene. Our results argue that although the substituted toluenyl moieties closely mimic the size and shape of the thymine residue, their more hydrophobic nature determines that they stack on DNA bases differently from the natural thymine residue and likely cause local conformational changes in duplex DNA.

Synthesis of C-aryl-nucleosides and O-aryl-glycosides via cuprate glycosylation

(Chemical Equation Presented) 2′-Deoxy-C-aryl-nucleosides have found increasing importance in studying DNA-DNA and DNA-protein interactions, as unnatural DNA-base pairs, and as oligonucleotide based fluorophores. Access to the required C-aryl-nucleosides

Nonpolar thymidine analogs

Nonpolar thymidine analogs are provided comprising a dihalogenated or trihalogenated base of the structure: where R1 is a sugar moiety; R2 is H or CH3; an imaging moiety or a cytotoxic moiety and X1 and X2

A set of nonpolar thymidine nucleoside analogues with gradually increasing size

(Chemical Equation Presented) We describe a series of nonpolar nucleoside analogues having similar shapes and gradually increasing size. The structure of the nucleobase thymine was mimicked with toluene derivatives, replacing 02/04 with hydrogen, fluorine, chlorine, bromine, and iodine. Glycosidic bonds were formed by reactions of lithiated 2,4-dihalotoluenes with a deoxyribonolactone derivative. Structural analysis by NMR showed similar conformations across the series. The compounds are useful for study of the biological recognition of nucleotides and nucleic acids.

Optimization of interstrand hydrophobic packing interactions within unnatural DNA base pairs

As part of an effort to expand the genetic alphabet, we have evaluated a large number of predominantly hydrophobic unnatural base pairs. We now report the synthesis and stability of unnatural base pairs formed between simple phenyl rings modified at diffe

Disiloxane-protected 2-deoxyribonolactone as an efficient precursor to 1,2-dideoxy-1-β-aryl-D-ribofuranoses

(matric presented) Aryl C-nucleosides are analogues of natural nucleosides where the bases have been replaced with aromatic moieties. Work herein describes the highly stereoselective syntheses of non-hydrogen-bonding carbocyclic derivatives using a disiloxane-protected 2-deoxy-D-ribono-1,4-lactone as a stable and readily accessible starting material. Unlike the bis(TBDMS)-protected congener, this compound enables the use of sterically congested ortho-substituted aryllithium reagents in the initial addition reaction.