Preparation of Pyrene‐Modified Purine and Pyrimidine Nucleosides via Suzuki—Miyaura Cross‐Couplings and Characterization of Their Fluorescent Properties.

Mayer, Elke; Valis, Linda; Huber, Robert; Amann, Nicole; Wagenknecht, Hans‐Achim

doi:10.1002/chin.200411188

Cited by 1 publication

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“…The first alternative to create applicable optical properties is to attach organic chromophores covalently to DNA bases ( 1). Over the last years we attached synthetically the organic chromophores pyrene, 47–49 ethynylpyrene, 50,51 phenothiazine, 52 benzpyrene, 53 and dipyrromethene boron difluoride (BODIPY) 54 to the natural DNA bases. The site of attachment of the fluorophores was chosen to be either the 5‐position of the pyrimidines (U/T and C) or the 8‐position of the purines (A and G).…”

Section: Dna Base Modifications and Base Substitutesmentioning

confidence: 99%

“…We use two different synthetic strategies to prepare these modified oligonucleotides 55 : (i) the DNA building block chemistry and (ii) the postsynthetic oligonucleotide modification. In the first case, [47][48][49]52,56 the nucleosides are halogenated in order to introduce a reactive functional group. These halogenated DNA bases represent the starting material for the subsequent Pdcatalyzed Suzuki-Miyaura-type cross-coupling reactions using the corresponding boronic acid or boronic acid esters of the chromophores.…”

Section: Dna Base Modifications and Base Substitutesmentioning

confidence: 99%

“…Extended coupling times have to be applied in many cases due to the enhanced steric hindrance of the chromophore-modified nucleoside phosphoramidite. Recently, we applied this modification strategy for the preparation of pyrene-modified nucleosides as models for charge transfer, 48,[57][58][59][60] pyrenemodified uridines to study of DNA-mediated electron transfer processes, 52,61,62 and pyrene-modified guanosine as a duplex-sensitive optical probe for DNA. 53,56,63 Alternatively to the DNA building block strategy, organic chromophores could be incorporated into oligonucleotides by solid-phase methodologies.…”

Section: Dna Base Modifications and Base Substitutesmentioning

confidence: 99%

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Fluorescent DNA Base Modifications and Substitutes: Multiple Fluorophore Labeling and the DETEQ Concept

Wagenknecht

2008

Annals of the New York Academy of Sciences

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There is an increasing need for fluorescent nucleic acid probes that are able to sense genetic variations without the application of enzymes. The incorporation of organic fluorophores either as DNA base modifications or as DNA base substitutions represents a powerful and versatile method for such new fluorescent DNA assays. Multiple labeling of oligonucleotides using several adjacent chromophore-modified DNA bases yields fluorescence enhancement and modulation that are sensitive to single-base mismatches in the complementary oligonucleotide. Charge transfer processes that cause fluorescence quenching are DNA-base mediated and occur over several base pairs distance. Our "DETEQ" setup, consisting of a fluorescence DNA base substitution and the charge acceptor as a second modification two base pairs away, allows the homogeneous detection of single-base mutations simply by fluorescence readout. This could lead to new DNA microarrays which are based on charge transfer processes and can be analyzed by commonly used fluorescence readout techniques.

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