Reduction of metal ions by boranephosphonate DNA

Roy, Subhadeeo; Olesiak, Magdalena; Pádár, Petra; McCuen, Heather Brummel; Caruthers, Marvin H.

doi:10.1039/c2ob26661j

Cited by 19 publications

(31 citation statements)

References 24 publications

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“…Fast isomer Slow isomer ESI+ (m/z) NH 3 10.37 (13) CH 3 NH 2 9.97 (11) Et 2 NH 9.49 (15) 8.03 (17) 6.92 (19) 2.14 (21) 8.89 (23) 8.76 (25) 6.75 (28) NH 2 8.49 (30) 9.32 (24) 8.59 (26) 10.43 (14) 10.28 (12) 10.15 (16) 8.56 (18) 7.39 (20) 2.62 (22) 903. 64 We also note that because this chemistry is orthogonal to other methods of DNA modification such as copper activated click reactions 18 or palladium catalyzed Stille couplings 19 , it opens avenues for labelling DNA with multiple functional groups and fluorophores.…”

Section: Nhr'r''mentioning

confidence: 99%

“…25 Concomitantly the boranephosphonate diester undergoes nucleophilic substitution by the solvent (water or methanol) to generate the phosphate diester or triester respectively. These observations hinted at a useful pathway to oxidatively activate the highly stable boranephosphonate internucleotide linkage towards nucleophilic substitution reactions.…”

Section: Substitution Reactions Of Boranephosphonate Dimers Activatedmentioning

confidence: 99%

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Oxidative Substitution of Boranephosphonate Diesters as a Route to Post-synthetically Modified DNA

et al. 2015

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The introduction of modifications into oligonucleotides is important for a large number of applications in the nucleic acids field. However, the method of solid-phase DNA synthesis presents significant challenges for incorporating many useful modifications that are unstable to the conditions for preparing synthetic DNA. Here we report that boranephosphonate diesters undergo facile nucleophilic substitution in a stereospecific manner upon activation by iodine. We have subsequently used this reactivity to post-synthetically introduce modifications including azides and fluorophores into DNA by first synthesizing boranephosphonate-linked 2'-deoxyoligonucleotides and then treating these oligomers with iodine and various nucleophiles. In addition, we show that this reaction is an attractive method for preparing stereodefined phosphorus-modified oligonucleotides. We have also examined the mechanism of this reaction and show that it proceeds via an iodophosphate intermediate. Beyond nucleic acids synthesis, due to the ubiquity of phosphate derivatives in natural compounds and therapeutics, this stereospecific reaction has many potential applications in organophosphorus chemistry.

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Section: Nhr'r''mentioning

confidence: 99%

Section: Substitution Reactions Of Boranephosphonate Dimers Activatedmentioning

confidence: 99%

Oxidative Substitution of Boranephosphonate Diesters as a Route to Post-synthetically Modified DNA

et al. 2015

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“…In fact, boranophosphate-modified oligonucleotides are up to 2-fold more resistant to nucleases than phosphorothioate-modified oligonucleotides (25). Also, boranophosphate-modified oligonucleotides also exert unique reducing properties under certain conditions (26). …”

Section: Introductionmentioning

confidence: 99%

Synthesis, properties, and biological activity of boranophosphate analogs of the mRNA cap: versatile tools for manipulation of therapeutically relevant cap-dependent processes

Kowalska

Nogal

Darżynkiewicz

et al. 2014

Nucleic Acids Research

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Modified mRNA cap analogs aid in the study of mRNA-related processes and may enable creation of novel therapeutic interventions. We report the synthesis and properties of 11 dinucleotide cap analogs bearing a single boranophosphate modification at either the α-, β- or γ-position of the 5′,5′-triphosphate chain. The compounds can potentially serve either as inhibitors of translation in cancer cells or reagents for increasing expression of therapeutic proteins in vivo from exogenous mRNAs. The BH3-analogs were tested as substrates and binding partners for two major cytoplasmic cap-binding proteins, DcpS, a decapping pyrophosphatase, and eIF4E, a translation initiation factor. The susceptibility to DcpS was different between BH3-analogs and the corresponding analogs containing S instead of BH3 (S-analogs). Depending on its placement, the boranophosphate group weakened the interaction with DcpS but stabilized the interaction with eIF4E. The first of the properties makes the BH3-analogs more stable and the second, more potent as inhibitors of protein biosynthesis. Protein expression in dendritic cells was 2.2- and 1.7-fold higher for mRNAs capped with m27,2′-OGppBH3pG D1 and m27,2′-OGppBH3pG D2, respectively, than for in vitro transcribed mRNA capped with m27,3′-OGpppG. Higher expression of cancer antigens would make mRNAs containing m27,2′-OGppBH3pG D1 and m27,2′-OGppBH3pG D2 favorable for anticancer immunization.

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“…,a nd Ag + into the corresponding nanosized metals, [15] such DNAa rrayse nable selective metal deposition at the preprogrammed bpDNA sites (see Figure 1B). Am inimumn umbero fb orane groups in close proximity is needed to inducen anoparticle formation on the templates,w hile high temperatures( 40 8C) lead to uncontrolled metal deposition at the bpDNAs ites.…”

Section: àmentioning

confidence: 98%

Biomolecules in Metal and Semiconductor Nanoparticle Growth

Baumann

Muhammed

Blanch

et al. 2015

Israel Journal of Chemistry

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Exerting control over the size, morphology, and complexity of metal and semiconductor nanoparticles and nanostructures is a requisite for exploring novel phenomena, and the potential applications of these nanomaterials. Bottom‐up colloidal chemistry syntheses can benefit from using biomolecules as active elements to influence the formation of inorganic nanoparticles. In this review, we will discuss how three main biomolecule types, (namely DNA; amino acids, peptides, and proteins; and enzymes), can affect the growth of metal and semiconductor nanoparticles. We will present and discuss the templating and non‐templating roles of those biomolecules, featuring key aspects and prospects of biomolecule‐assisted metal and semiconductor nanoparticle growth.

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Reduction of metal ions by boranephosphonate DNA

Cited by 19 publications

References 24 publications

Oxidative Substitution of Boranephosphonate Diesters as a Route to Post-synthetically Modified DNA

Oxidative Substitution of Boranephosphonate Diesters as a Route to Post-synthetically Modified DNA

Synthesis, properties, and biological activity of boranophosphate analogs of the mRNA cap: versatile tools for manipulation of therapeutically relevant cap-dependent processes

Biomolecules in Metal and Semiconductor Nanoparticle Growth

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