31747-59-8Relevant academic research and scientific papers
Methoxyphenol and dihydrobenzofuran as oxidizable labels for electrochemical detection of DNA
Simonova, Anna,Balintov, Jana,Pohl, Radek,Havran, Ludk,Fojta, Miroslav,Hocek, Michal
, p. 1703 - 1712 (2014)
4-Hydroxy-3-methoxyphenyl (MOP) and 2,3-dihydrobenzofuran- 5-yl (DHB) groups were tested as potential new oxidizable labels for electrochemical detection of DNA. The corresponding 5-aryl-cytosine and 7-aryl-7-deazaadenine 2′-deoxyribonucleoside triphospha
Phosphine-Free Stille-Migita Chemistry for the Mild and Orthogonal Modification of DNA and RNA
Krause, André,Hertl, Alexander,Muttach, Fabian,J?schke, Andres
, p. 16613 - 16619 (2014)
An optimized catalyst system of [Pd2(dba)3] and AsPh3 efficiently catalyzes the Stille reaction between a diverse set of functionalized stannanes and halogenated mono-, di- and oligonucleotides. The methodology allows for the facile conjugation of short and long nucleic acid molecules with moieties that are not compatible with conventional chemical or enzymatic synthesis, among them acid-, base-, or fluoride-labile protecting groups, fluorogenic and synthetically challenging moieties with good to near-quantitative yields. Notably, even azides can be directly introduced into oligonucleotides and (deoxy)nucleoside triphosphates, thereby giving direct access to "clickable" nucleic acids.
Exploiting Substrate Promiscuity to Develop Activity-Based Probes for Ten-Eleven Translocation Family Enzymes
Ghanty, Uday,Denizio, Jamie E.,Liu, Monica Yun,Kohli, Rahul M.
, p. 17329 - 17332 (2018)
Ten-eleven translocation (TET) enzymes catalyze repeated oxidations of 5-methylcytosine in genomic DNA. Because of the challenges of tracking reactivity within a complex DNA substrate, chemical tools to probe TET activity are limited, despite these enzyme's crucial role in epigenetic regulation. Here, building on precedents from related Fe(II)/α-ketoglutarate-dependent dioxygenases, we show that TET enzymes can promiscuously act upon cytosine bases with unnatural 5-position modifications. Oxidation of 5-vinylcytosine (vC) in DNA results in the predominant formation of a 5-formylmethylcytosine product that can be efficiently labeled to provide an end-point read-out for TET activity. The reaction with 5-ethynylcytosine (eyC), moreover, results in the formation of a high-energy ketene intermediate that can selectively trap any active TET isoform as a covalent enzyme-DNA complex, even in the complex milieu of a total cell lysate. Exploiting substrate promiscuity therefore offers a new and needed means to directly track TET activity in vitro or in vivo.
Phenothiazine-linked nucleosides and nucleotides for redox labelling of DNA
Simonova, Anna,Havran, Luděk,Pohl, Radek,Fojta, Miroslav,Hocek, Michal
, p. 6984 - 6996 (2017/09/01)
Nucleosides and 2′-deoxyribonucleoside triphosphates (dNTPs) bearing phenothiazine (PT) attached to a nucleobase (cytosine or 7-deazaadenine) either directly or through an acetylene linker were prepared through Suzuki or Sonogashira cross-coupling and triphosphorylation, and were studied as building blocks for polymerase construction of modified DNA. The directly PT-substituted dNTPs were better substrates for polymerases than the alkyne-linked dNTPs but all of them were used in enzymatic synthesis of DNA using primer extension, nicking enzyme amplification, PCR or 3′-tail labelling by terminal deoxynucleotidyl transferase. The phenothiazine served as an oxidizable redox label (giving two analytically useful signals of oxidation on electrode) for nucleosides and DNA and was also used in orthogonal combination with previously developed benzofurazane or nitrophenyl labels for redox coding of DNA bases. Therefore, the title PT-linked dNTPs are useful additions to the portfolio of nucleotides for enzymatic synthesis of redox-labelled DNA for electrochemical analysis.
A new efficient stereoselective method for the synthesis of (E)-5-aminoallyl-pyrimidine-5′-triphosphates using palladium-catalyzed heck reaction
Kore, Anilkumar R.,Senthilvelan, Annamalai,Shanmugasundaram, Muthian,Sandoval, David,Pardo, Andrew
, p. 221 - 228 (2015/04/27)
An efficient overall two-step strategy for the synthesis of, starting from commercially available pyrimidine-5′-triphosphate is described. The method involves regioselective iodination of pyrimidine-5′-triphosphate, followed by the palladium-catalyzed Heck coupling with allylamine. The catalytic reaction is highly stereoselective and compatible with many functional groups present in the reactants.
Aminophenyl- and nitrophenyl-labeled nucleoside triphosphates: Synthesis, enzymatic incorporation, and electrochemical detection
Cahova, Hana,Havran, Ludek,Brazdilova, Petra,Pivonkova, Hana,Pohl, Radek,Fojta, Miroslav,Hocek, Michal
supporting information; experimental part, p. 2059 - 2062 (2009/02/06)
(Chemical Equation Presented) Primer extension is used to incorporate labeled nucleoside triphosphates into oligonucleotides (ONs). Aminophenyl and nitrophenyl modifications serve as electrochemical labels that are detectable by either oxidation or reduct
