DNA Modification under Mild Conditions by Suzuki–Miyaura Cross‐Coupling for the Generation of Functional Probes

Lercher, Lukas; McGouran, Joanna F.; Kessler, Benedikt M.; Schofield, Christopher J.; Davis, Benjamin G.

doi:10.1002/anie.201304038

Cited by 119 publications

(127 citation statements)

References 68 publications

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“…In the field of homogenous Pd-mediated chemistry, Davis developed biomolecule compatible Pd-complexes and strategies to tag and modify peptides, sugars [19], proteins [20,21 ] and DNA [23]. Davis elegantly exemplified the in vitro labelling of biomolecules by incorporation of various chemical tags by chemical (e.g.…”

Section: Homogenous Pd-mediated Chemistrymentioning

confidence: 99%

Palladium-mediated chemistry in living cells

Chankeshwara

Indrigo

Bradley

2014

Current Opinion in Chemical Biology

103

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Section: Homogenous Pd-mediated Chemistrymentioning

confidence: 99%

Palladium-mediated chemistry in living cells

Chankeshwara

Indrigo

Bradley

2014

Current Opinion in Chemical Biology

103

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“…This has been used to produce fluorescent phenyl-guanine or benzothiophene-guanine analogues 96 . A more reactive 5-iodothymine has also been explored that could undergo the coupling reaction at lower temperatures 97 . For Stille coupling, both 5-iodothymine and 2-iodoadenine have been explored to react with high excess of organostannane under the catalysis of palladium(0) triarylphosphine, heated to 60 °C in dimethylformamide 98,99 .…”

Section: Labelling Methodsmentioning

confidence: 99%

Fluorescent nucleobases as tools for studying DNA and RNA

2017

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Understanding the diversity of dynamic structures and functions of DNA and RNA in biology requires tools that can selectively and intimately probe these biomolecules. Synthetic fluorescent nucleobases that can be incorporated into nucleic acids alongside their natural counterparts have emerged as a powerful class of molecular reporters of location and environment. They are enabling new basic insights into DNA and RNA, and are facilitating a broad range of new technologies with chemical, biological and biomedical applications. In this Review, we will present a brief history of the development of fluorescent nucleobases and explore their utility as tools for addressing questions in biophysics, biochemistry and biology of nucleic acids. We provide chemical insights into the two main classes of these compounds: canonical and non-canonical nucleobases. A point-by-point discussion of the advantages and disadvantages of both types of fluorescent nucleobases is made, along with a perspective into the future challenges and outlook for this burgeoning field.

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“…[35,42] [176] N-Arylierung ist eine leistungsfähige Methode zur Herstellung von N-C(sp 2 )-Bindungen in vielen Wirkstoffmolekülen und komplexen Naturstoffen. [182][183][184][185] Eine breite Auswahl von Arylhalogeniden und Arylboronsäuren ist im Handel erhältlich und steht als Bausteine fürd ie Modifikation von Aminen mittels der genannten Metall-katalysierten Reaktionen zur Verfügung. Eher routinemäßig angewendete Methoden fürd ie Arylierung von Aminen sind Übergangsmetall-katalysierte Kreuzkupplungen wie die Buchwald-Hartwig-Reaktion, [36,177,178] die Chan-Lam-Reaktion [179][180][181] sowie Ullmann-Goldberg-Kupplungen.…”

Section: Lysinarylierungunclassified

Arylierungschemie für die Biokonjugation

et al. 2019

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Mittels Biokonjugationschemie können modifizierte Biomoleküle hergestellt werden, deren Funktionsumfang das natürliche Maß übersteigt. Hierbei ist die Entwicklung hocheffizienter und selektiver Biokonjugationsreaktionen von Bedeutung, die unter milden, biokompatiblen Bedingungen ablaufen. Vielversprechend sind hierbei Verfahren, bei denen Bindungen zwischen einem Nukleophil und einem sp2‐hybridisierten Kohlenstoffatom gebildet werden, wodurch in manchen Fällen Moleküle mit einzigartigen Eigenschaften erhalten werden können. In diesem Aufsatz werden Biokonjugationsstrategien für die Arylierung von Schwefel, Stickstoff, Selen, Sauerstoff und Kohlenstoff sowie ihre Anwendungen für die Modifikation von Peptiden, Proteinen, Kohlenhydraten und Nukleinsäuren zusammengefasst.

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DNA Modification under Mild Conditions by Suzuki–Miyaura Cross‐Coupling for the Generation of Functional Probes

Cited by 119 publications

References 68 publications

Palladium-mediated chemistry in living cells

Palladium-mediated chemistry in living cells

Fluorescent nucleobases as tools for studying DNA and RNA

Arylierungschemie für die Biokonjugation

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