Multistep DNA‐Templated Reactions for the Synthesis of Functional Sequence Controlled Oligomers

McKee, Mireya L.; Milnes, Phillip J.; Bath, Jonathan; Stulz, Eugen; Turberfield, Andrew J.; O’Reilly, Rachel K.

doi:10.1002/anie.201002721

Cited by 145 publications

(78 citation statements)

References 21 publications

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“…[22][23][24][25][26][27] Furthermore, depending on the feed ratio, solvent and co-monomer, apparently perfect alternating copolymers could be prepared provided that the rate constant for cross-propagation to DPE (M 2 ) is significantly higher than the rate constant for self-propagation of the non-DPE monomer (M 1 ) i.e. k 12 << k 11 . One such comonomer is styrene which can form alternating copolymers with DPE but the propensity for alternation is highly dependent upon solvent polarity.…”

Section: Resultsmentioning

confidence: 99%

Monomer Sequence Control via Living Anionic Copolymerization: Synthesis of Alternating, Statistical, and Telechelic Copolymers and Sequence Analysis by MALDI ToF Mass Spectrometry

et al. 2015

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(2015) 'Monomer sequence control via living anionic copolymerization : synthesis of alternating, statistical, and telechelic copolymers and sequence analysis by MALDI ToF mass spectrometry. ', Macromolecules., 48 (3). pp. 610-628.Further information on publisher's website:Publisher's copyright statement:This document is the Accepted Manuscript version of a Published Work that appeared in nal form in Macromolecules, copyright c 2015 American Chemical Society after peer review and technical editing by the publisher. To access the nal edited and published work see http://dx.doi.org/10.1021/ma5016038. Additional information:Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. 3LE. United Kingdom ABSTRACT: Diphenylethylene (DPE) is a monomer which has attracted significant interest from both academia and industry. DPE can undergo (co)polymerization by living anionic polymerization but is incapable of forming a homopolymer due to steric hindrance. Herein the copolymerization of DPE and 1,1-bis(4-tert-butyldimethylsiloxyphenyl)ethylene (DPE-OSi)with styrene or butadiene is described in order to produce (functional) copolymers with controlled co-monomer sequences -either alternating or telechelic. The copolymer sequences are inherently controlled by relative reactivity ratios, which in turn can be tuned by both monomer structure and by the polarity of the polymerization solvent. The composition of the copolymers prepared in this study were analyzed by 1 H NMR spectroscopy and MALDI ToF 2 mass spectrometry, the latter offering a unique opportunity to demonstrate perfect alternating sequences and insight into other sequences such as telechelic polymers.

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Section: Resultsmentioning

confidence: 99%

Monomer Sequence Control via Living Anionic Copolymerization: Synthesis of Alternating, Statistical, and Telechelic Copolymers and Sequence Analysis by MALDI ToF Mass Spectrometry

et al. 2015

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“…Different DNA switching devices [106] or machines, such as tweezers [107,108], walkers [109,110], rotors [111,112] or gears [113] were developed and their potential utilization as optoelectronic devices [114][115][116], as dictated molecular carriers [117,118], and as functionalized units for programmed synthesis and biocatalysis [119][120][121] were reported. By conjugating metal-ion-functionalized G-quadruplex nanostructures to DNA machines, the unique catalytic and optical properties of the G-quadruplexes may be used to follow the switchable operation of the DNA machines or, alternatively, allow the use of the DNA machines as scaffolds for programmed synthesis or for switchable photonics.…”

Section: Metalloporphyrins As Labels For Dna Machinesmentioning

confidence: 99%

Metalloporphyrin/G-quadruplexes: From basic properties to practical applications

Golub

Lü

Willner

2015

J. Porphyrins Phthalocyanines

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Guanine-rich nucleic acids stimulate the formation of planar, Hoogsteen hydrogen bonds-stabilized G-quartet (1), Fig. 1(a). The following p-p stacking of G-quartets, leads to the self-assembly of G-quadruplexes. These G-quadruplexes reveal cation-induced stabilization by means of coordination, mainly in the presence of monovalent ions, generally in the order of stabilization of K + > NH 4 + > Rb + > Na + > Cs + > Li + [1]. The resulting G-quadruplexes may adopt various topologies, such as parallel, anti-parallel or mixed strand configurations [2]. For example, Fig. 1(b) outlines various forms of four-layer guanine-quartets exhibiting different configurations: (i) edge-loop dimeric hairpin structure, (ii) diagonal-loop dimeric hairpin, (iii) unimolecular single strand with diagonal central loop, and (iv) unimolecular edge-type ABSTRACT: Guanine-rich single-stranded nucleic acids self-assemble into G-quadruplex nanostructures (predominately in the presence of K + -ions). Metalloporphyrins bind to the G-quadruplex nanostructures to form supramolecular assemblies exhibiting unique catalytic, electrocatalytic and photophysical properties. This paper addresses the advances in the characterization and the implementation of the metalloporphyrin/G-quadruplexes complexes for various applications. Out of the different complexes, the most extensively studied complexes are the hemin/G-quadruplex horseradish peroxidase-mimicking DNAzyme and the Zn(II)-protoporphyrin IX-functionalized G-quadruplex. Specifically, the hemin/Gquadruplex was found to act as a catalyst for driving different chemical transformations that mimic the native horseradish peroxidase enzyme, and, also, to function as an electrocatalyst for the reduction of H 2 O 2 . Also, the hemin/G-quadruplex stimulates interesting photophysical and photocatalytic processes such as the electron-transfer quenching of semiconductor quantum dots or the chemiluminescence resonance energy transfer to semiconductor quantum dots. Alternatively, Zn(II)-protoporphyrin IX associated with G-quadruplexes exhibit intensified fluorescence properties. Beyond the straight forward application of the metalloporphyrin/G-quadruplexes as catalysts that stimulate different chemical transformations, the specific catalytic, electrocatalytic and photocatalytic functions of hemin/G-quadruplexes are heavily implemented to develop sophisticated colorimetric, electrochemical, and optical sensing platforms. Also, the unique fluorescence properties of Zn(II)-protoporphyrin IX-functionalized G-quadruplexes are applied to develop fluorescence sensing platforms. The article exemplifies different sensing assays for analyzing DNA, ligand-aptamer complexes and telomerase activity using the metalloporphyrins/Gquadruplexes as transducing labels. Also, the use of the hemin/G-quadruplex as a probe to follow the operations of DNA machines is discussed.

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“…Hence, in 2010 we developed a new strategy for the synthesis of ordered functional oligomeric materials by means of sequential DNA-templated reactions, without the need for addition of reagents or the purification of intermediates (37). In principle this mechanism allows for the synthesis of products without a length restriction.…”

Section: Dna-templated Chemistrymentioning

confidence: 99%

DNA-Templated Chemistries for Sequence Controlled Oligomer Synthesis

Milnes

O’Reilly

2014

ACS Symposium Series

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Multistep DNA‐Templated Reactions for the Synthesis of Functional Sequence Controlled Oligomers

Cited by 145 publications

References 21 publications

Monomer Sequence Control via Living Anionic Copolymerization: Synthesis of Alternating, Statistical, and Telechelic Copolymers and Sequence Analysis by MALDI ToF Mass Spectrometry

Monomer Sequence Control via Living Anionic Copolymerization: Synthesis of Alternating, Statistical, and Telechelic Copolymers and Sequence Analysis by MALDI ToF Mass Spectrometry

Metalloporphyrin/G-quadruplexes: From basic properties to practical applications

DNA-Templated Chemistries for Sequence Controlled Oligomer Synthesis

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