13389-03-2Relevant articles and documents
Preparation of pyrenyl-modified nucleosides via Suzuki-Miyaura cross-coupling reactions
Amann, Nicole,Wagenknecht, Hans-Achim
, p. 687 - 691 (2002)
The modified nucleosides 5-pyrenyl-2′-deoxyuridine (1) and 8-pyrenyl-2′-deoxyguanosine (2) were synthesized via palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of pyren-1-yl boronic acid (3) to either 5-iodo-2′-deoxyuridine (4), or 8-bromo-2′-deoxyguanosine (7), respectively. No protecting groups for the hydroxy and amino functions of the nucleoside are needed during the preparation. Both pyrene derivatives are suitable nucleoside models for the spectrosopic investigation of reductive electron transfer (in 1), or oxidative hole transfer (in 2).
8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells
Lin,Cheng,Ishiguro,Sartorelli
, p. 1194 - 1198 (1985)
A variety of 8-substituted guanosine and 2'-deoxyguanosine derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells in culture. The most active agents in the guanosine series were 8-substituted -N(CH3)2, -NHCH3, -NH2, -OH, and -SO2CH3, which caused 68, 42, 34, 33, and 30% of erythroleukemia cells to attain benzidine positivity, a functional measure of maturation, at concentrations of 5, 1, 0.4, 5, and 5 mM, respectively. The 8-OH derivative of the 2'-deoxyguanosine series produced comparable activity, causing 62% benzidine-positive cells at a level of 0.2 mM. These findings indicate that 8-substituted analogues of guanosine and 2'-deoxyguanosine have the potential to terminate leukemia cell proliferation through conversion to end-stage differentiated cells.
Selective C8-Metalation of Purine Nucleosides via Oxidative Addition
Kampert, Florian,Brackemeyer, Dirk,Tan, Tristan Tsai Yuan,Ekkehardt Hahn
, p. 4181 - 4185 (2018)
8-Bromo-2′-deoxy-3′,5′-di-O-acetylguanosine (1), 8-bromo-2′,3′,5′-tri-O-acetylguanosine (2), 8-bromo-2′-deoxy-3′,5′-di-O-acetyladenosine (3), and 8-bromo-2′,3′,5′-tri-O-acetyladenosine (4) react with [Pd(PPh3)4] via a C8-Br oxidative addition to give the C8-palladated azolato complexes [5]-[8] featuring an unprotonated N7 ring nitrogen atom. The complexes feature diastereotopic trans-disposed triphenylphosphine ligands, which allowed the determination of 2JPP for complexes of the type trans-[PdL2(PPh3)2] (2JPP = 442 Hz for [7]). In addition, two complex molecules of [7] form a trans-Watson-Crick/Hoogsteen AA base pair in the solid state. N7-protonation of the guanosine-derived complexes [5] and [6] with HBF4·Et2O and of adenosine-derived complexes [7] and [8] using lutidinium triflate yields complexes [9]BF4 and [10]BF4 and complexes [11]OTf and [12]OTf bearing protic NH,NR-NHC ligands derived from guanosine and adenosine, respectively.
Synthesis of oligonucleotides bearing an arylamine modification in the C8-position of 2′-deoxyguanosine
Meier,Graesl,Detmer,Marx
, p. 691 - 694 (2005)
C8-Arylamine-dG adducts were converted into their corresponding 5′-0-DMTr-3′-0-phosphoramidite-C8-arylamine-dG derivatives. These compounds were used for the automated synthesis of site-specifically modified oligonucleotides. The oligonucleotides were stu
An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson-Crick versus Hoogsteen base pairing
Schlitt, Katherine M.,Millen, Andrea L.,Wetmore, Stacey D.,Manderville, Richard A.
, p. 1565 - 1571 (2011)
Pyrrole- and indole-linked C8-deoxyguanosine nucleosides act as fluorescent reporters of H-bonding specificity. Their fluorescence is quenched upon Watson-Crick H-bonding to dC, while Hoogsteen H-bonding to G enhances emission intensity. The indole-linked probe is ～ 10-fold brighter and shows promise as a fluorescent reporter of Hoogsteen base pairing. The Royal Society of Chemistry 2011.
Synthesis of Phosphoramidite Monomers Equipped with Complementary Bases for Solid-Phase DNA Oligomerization
Romero-Pérez, Sonia,López-Martín, Isabel,Martos-Maldonado, Manuel C.,Somoza, álvaro,González-Rodríguez, David
supporting information, p. 41 - 45 (2020/01/03)
We describe the preparation of two monomers that bear complementary nucleobases at the edges (guanine-2′-deoxycytidine and 2-aminoadenine-2′-deoxyuridine) and that are conveniently protected and activated for solid-phase automated DNA synthesis. We report the optimized synthetic routes leading to the four nucleobase derivatives involved, their cross-coupling reactions into dinucleobase-containing monomers, and their oligomerization in the DNA synthesizer.
Tracking Hole Transport in DNA Hairpins Using a Phenylethynylguanine Nucleobase
Brown, Kristen E.,Singh, Arunoday P. N.,Wu, Yi-Lin,Mishra, Ashutosh Kumar,Zhou, Jiawang,Lewis, Frederick D.,Young, Ryan M.,Wasielewski, Michael R.
supporting information, p. 12084 - 12092 (2017/09/07)
The hole transport dynamics of DNA hairpins possessing a stilbene electron acceptor and donor along with a modified guanine (G) nucleobase, specifically 8-(4′-phenylethynyl)deoxyguanosine, or EG, have been investigated. The nearly indistinguishable oxidation potentials of EG and G and unique spectroscopic characteristics of EG+? make it well-suited for directly observing transient hole occupation during charge transport between a stilbene electron donor and acceptor. In contrast to the cation radical G+?, EG+? possesses a strong absorption near 460 nm and has a distinct Raman-active ethynyl stretch. Both spectroscopic characteristics are easily distinguished from those of the stilbene donor/acceptor radical ion chromophores. Employing EG, we observe its role as a shallow hole trap, or as an intermediate hole transport site when a deeper trap state is present. Using a combination of ultrafast absorption and stimulated Raman spectroscopies, the hole-transport dynamics are observed to be similar in systems having EG vs G bases, with small perturbations to the charge transport rates and yields. These results show EG can be deployed at specified locations throughout the sequence to report on hole occupancy, thereby enabling detailed monitoring of the hole transport dynamics with base-site specificity.
