220952-00-1Relevant articles and documents
Selective Chemical Functionalization at N6-Methyladenosine Residues in DNA Enabled by Visible-Light-Mediated Photoredox Catalysis
Nappi, Manuel,Hofer, Alexandre,Balasubramanian, Shankar,Gaunt, Matthew J.
supporting information, p. 21484 - 21492 (2021/01/11)
Selective chemistry that modifies the structure of DNA and RNA is essential to understanding the role of epigenetic modifications. We report a visible-light-activated photocatalytic process that introduces a covalent modification at a C(sp3)-H bond in the methyl group of N6-methyl deoxyadenosine and N6-methyl adenosine, epigenetic modifications of emerging importance. A carefully orchestrated reaction combines reduction of a nitropyridine to form a nitrosopyridine spin-trapping reagent and an exquisitely selective tertiary amine-mediated hydrogen-atom abstraction at the N6-methyl group to form an α-amino radical. Cross-coupling of the putative α-amino radical with nitrosopyridine leads to a stable conjugate, installing a label at N6-methyl-adenosine. We show that N6-methyl deoxyadenosine-containing oligonucleotides can be enriched from complex mixtures, paving the way for applications to identify this modification in genomic DNA and RNA.
Photocontrol over cooperative porphyrin self-assembly with phenylazopyridine ligands
Hirose, Takashi,Helmich, Floris,Meijer
supporting information, p. 304 - 309 (2013/02/23)
The cooperative self-assembly of chiral zinc porphyrins is regulated by a photoresponsive phenylazopyridine ligand (1; see picture). Porphyrin stacks depolymerize into dimers upon axial ligation and the strength of the coordination is regulated by its pho
Cross coupling strategies towards the synthesis of the streptonigrin CD moiety
Crous, Renier,Dwyer, Catherine,Holzapfel, Cedric W.
, p. 721 - 726 (2007/10/03)
An efficient route to an appropriate model of the streptonigrin 4- phenylpyridine CD moiety is reported. 4-Chloro-3-nitropyridine was found to be the key precursor and its reactivity in cross coupling reactions was further investigated.