6875-83-8Relevant academic research and scientific papers
Preparation of stilbene-tethered nonnatural nucleosides for use with blue-fluorescent antibodies
Chen,Beuscher IV,Stevens,Wirsching,Lerner,Janda
, p. 1725 - 1732 (2007/10/03)
The synthesis of the first examples of stilbene-tethered hydrophobic C-nucleosides is described. Compounds of this type are targeted for use with our recently reported "blue-fluorescent antibodies with the aim of probing native and nonnatural DNA. The nucleophilic addition of aryl Grignard reagents to either a protected 2′-deoxy-1′-chloro-ribofuranose or a protected 2′-deoxy-ribonolactone was the key synthetic step and afforded C-nucleosides in good yields. Both routes resulted in a final product that was ≥ 90% of the β-anomer. Amide- and ether-based linkers for attachment of trans-stilbene to the nucleobase were assessed for utility during synthesis and in binding of the ligands to a blue-fluorescent monoclonal antibody. X-ray structures of each complex were obtained and serve as a guideline for second-generation stilbene-tethered C-nucleosides. The development of these hydrophobic nucleosides will be useful in current native and nonnatural DNA studies and invaluable for investigations regarding novel, nonnatural genomes in the future.
A One-Step Conversion of p-Methoxybenzyl Ethers into Methoxymethyl Ethers by the Action of Dimethoxymethane in the Presence of Tin(II) Bromide and Bromomethyl Methyl Ether
Oriyama, Takeshi,Kimura, Mikio,Koga, Gen
, p. 885 - 887 (2007/10/02)
The combined use of dimethoxymethane with catalytic amounts of tin(II) bromide and bromomethyl methyl ether cleaves p-methoxybenzyl ethers to give methoxymethyl ethers in good yields.The chemoselective conversion of p-methoxybenzyl ethers in the presence of the benzyl ether function into methoxymethyl ethers has also occurred successfully.
